BWW Exclusive: THE 101 GREATEST MUSICAL THEATRE CHARACTERS (1940-2020) - from Annie to Elphaba, from Henry Higgins to Alexander Hamilton

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BWW Exclusive: THE 101 GREATEST MUSICAL THEATRE CHARACTERS (1940-2020) - from Annie to Elphaba, from Henry Higgins to Alexander Hamilton

"Just because you are a character doesn't mean that you have character." --Winston Wolf (Harvey Keitel) in "Pulp Fiction"

Get ready to debate! Sports, politics and musical theatre, the three subjects that cause the most arguments. But it's not always safe arguing politics--you either preach to the converted; your words land on deaf ears; or, sadly, everybody's so entrenched on their opposite sides that they will never move. Which leaves sports and musical theatre. But sports always have some objective angle--a score, a batting average, how many interceptions Jameis Winston threw; how can you really argue the dry numbers? Musical theatre, on the other hand, is a hotbed of feelings, tastes and emotions, all subjective, so it's more difficult arguing the "feels" rather than the "facts."

But it's also a lot more fun.

That's why I use a rubric in determining these lists. Although still subjective, it attaches numbers to each entry, in this case musical theatre characters/roles. For the record, the top score received a 98.9, while #101 got a 77.0. The criteria this time was simple: quality of songs (34 points); popularity/memorability/iconic status (33 points); and the character's emotional or comedic range (33 points). Most of these characters carry the greatest shows and songs in theatre history; only one character below doesn't really sing (that would be Man in Chair from THE DROWSY CHAPERONE, who made the list even though he narrates the show and only joins in musically at the end).

This list starts 80 years ago, at the start of the Golden Age of Musicals (Rodgers & Hammerstein on Broadway for the first time with "Oklahoma!" in 1943) and goes all the way to today, with a couple from 2018-2019. So, don't expect anything pre-1940, like the title characters from PORGY AND BESS or Reno Sweeney in ANYTHING GOES.

A "spread the wealth" philosophy is used in concocting something like this. Still, three shows have three characters on the list: GUYS AND DOLLS, MY FAIR LADY and LES MISERABLES. Several more have two characters/roles on the list: HAMILTON, WICKED, SWEENEY TODD, EVITA, MAN OF LA MANCHA, THE KING AND I, CABARET, LITTLE SHOP OF HORRORS, CHICAGO, JESUS CHRIST SUPERSTAR, MAME, COMPANY, ANNIE, INTO THE WOODS, SOUTH PACIFIC, THE PRODUCERS and WEST SIDE STORY.

Sometimes hard decisions had to be made...Pippin or the Leading Player? Nellie or Emile? And how can I pick supporting players over Seymour and Audrey in LITTLE SHOP? Sometimes some of the parts work best in movies (Mary Poppins, I'm talking to you). Sadly, some fantastic shows have great characters, but none that made the 101, like CAMELOT, FOLLIES, THE WIZ, KISS ME KATE, JOSEPH AND THE AMAZING TECHNICOLOR DREAMCOAT, HAIR, PROMISES, PROMISES, THE LION KING, and GODSPELL. For the record, the title character in SHREK landed at #102, barely missing the list, and #103 was Captain Hook from PETER PAN.

The first section of the list, the one that's roughly #80-#101, is peppered with a lot of character parts--Disney villains, animals, nerdy youths, puppets, and suicidal teens. But then, around the halfway point, you'll find mostly iconic roles, giants of musical theatre, one after the other after the other. Each one a goldmine, the best characters from the greatest shows. Any one of them could reside at #1, but which one ultimately gets it? Try to guess right now, and then scroll down to the bottom of the 101 to see if you're correct.

I write these lists to get my mind off the craziness of the world and the pandemic, and hopefully it will momentarily get your minds off it as well. So sit back, scroll through the whole thing, and get ready for a friendly debate. Here they are, counting down from #101 all the way down to #1. Have fun!

THE 101 GREATEST MUSICAL THEATRE CHARACTERS/ROLES (1940-2020)

101. Mayoress Cora Hoover Hooper [ANYONE CAN WHISTLE; 1964]

The show, about a corrupt mayor's staging of a fake miracle to rile up tourism, lasted only 9 regular performances on Broadway and may be forgotten today. But not the lead role of the crooked Mayoress, one of the more under-appreciated roles in Stephen Sondheim's canon. She may not get to sing the memorable title song, but she gets to steal the show. (Angela Lansbury inhabited the role in its way-too-short Broadway run.) Key songs featuring the character: "Me and My Town," "Miracle Song," "A Parade in Town," "I've Got You to Lean On," and "Cora's Chase (The Cookie Chase)."

100. Leo Frank [PARADE; 1999]

Leo Frank is an actual person, a Jewish factory manager accused of raping and murdering a teenage girl in 1913. When studying the evidence, many people think he didn't do it, but the Milledgeville lynch mob in PARADE thinks differently. It seems an unlikely musical idea, but Leo Frank is such a great role, a prosecuted "innocent" man, hence his inclusion here. This is the show that introduced Broadway to the phenomenal and still very underrated Jason Robert Brown. Key songs featuring the character: "How Can I Call This Home?", "Leo at Work/What Am I Waiting For?", "Factory Girls/Come Up to My Office," Leo's Statement: It's Hard to Speak My Heart," "This Is Not Over Yet," "Newt Lee's Reprise," "All the Wasted Time," and "Sh'ma."

99. Orin Scrivello, DDS [LITTLE SHOP OF HORRORS; 1982]

Audrey's abusive boyfriend also happens to be that redundancy...a sadistic dentist. Key songs featuring the character: "Dentist!" and "Now (It's Just the Gas)."

98. Diana Morales [A CHORUS LINE; 1975]

As one of the hopeful dancers vying for a spot in A CHORUS LINE, Diana is best known for failing high school theatre class, especially in their various Method-like activities, and her reactions to the death of an insensitive teacher named Mr. Karp. She also leads one of the great songs about the theatre: "What I Did for Love." Key songs featuring the character: "I Hope I Get It," "Nothing," "One," and "What I Did for Love."

97. Kate Monster [AVENUE Q; 2003]

Kate, a Monster, is the first puppet character on the list (scroll down to find the other, which also happens to be a monster but from a different show). A kindergarten teaching assistant, she yearns to open her own school, one designed just for monsters. A quibbler, charismatic, anxious, lovable, with a beautiful heart to match. Key songs featuring the character: "It Sucks to be Me," "Everyone's a Little Bit Racist," "The Internet is for Porn," "Mix Tape," "You Can Be as Loud as the Hell You Want (When You're Makin' Love)," "Fantasies Come True," "There's a Fine, Fine Line," "The More You Ruv Someone," "I Wish I Could Go Back to College," and "For Now."

96. William Barfee [THE 25TH ANNUAL PUTNAM COUNTY SPELLING BEE; 2005]

Barfee, the nerdy kid who has a peanut allergy, spells his words with his foot. Usually Barfee is played as a short, slightly overweight, dweeby nose-picker. But I've also seen him played as a nit-picky androgynous geek with a heavy dose of OCD and a voice like Kiki DuRane on bitch pills. Either way, it works, and we root for this ultimate outsider. His big number, "Magic Foot," is like a one-man Bob Fosse routine if done right. Key songs featuring the character: "The Twenty-Fifth Annual Putnam County Spelling Bee," "Pandemonium," "Magic Foot," "Second," "Weltanschauung," and "Barfee and Olive Pas de Deux."

95. Snoopy [YOU'RE A GOOD MAN, CHARLIE BROWN; 1967]

The world's most famous beagle climbs on top of his doghouse to become a World War I flying ace. His battles against the dreaded Red Baron are epic. Key songs featuring the character: "Snoopy," "The Book Report," "The Red Baron," "Peanuts Potpourri," "Suppertime," and "Happiness."

94. Elder Arnold Cunningham [THE BOOK OF MORMON; 2011]

The ultimate dweeb, a slovenly schlub, an overweight Nerd with a capital N; he's like a white Mormon Urkel. A Star Wars and Star Trek enthusiast, he may not be self-assured, and he may not tell the truth often, but he's still all heart. And he may have been abandoned all of his life, but on his current Mormon Mission in Uganda, he has a best friend in Elder Price who can never leave his side. Key songs featuring the character: "Hello," "Two By Two," "You and Me (But Mostly Me)," "Hasa Diga Eebowai," "I Am Here for You," "All American Prophet," "Man Up," "Making Things Up Again," "Baptize Me," "I Am Africa," and "Tomorrow Is a Latter Day."

93. Moritz Stiefel [SPRING AWAKENING; 2006]

Moritz, the most troubled and anxious of the SPRING AWAKENING gang, is probably best known for his hair-wild, insane, unpredictable, a follicle-mirror of his inner turmoil. Key songs featuring the character: "The Bitch of Living," "My Junk," "Touch Me," "The Dark I Know Well," "And Then There Were None," "The Mirror-Blue Night," "I Believe," "The Guilty Ones," "Don't Do Sadness/Blue Wind," and "Those You've Known."

92. Ti Moune [ONCE ON THIS ISLAND; 1990]

Ti Moune, a peasant girl, is the central figure of a story passed down through the ages, a story of life, love, heartbreak, and hope. Key songs featuring the character: "One Small Girl," "Waiting for Life," "Discovering Daniel," "Pray," "Forever Yours," "Ti Moune," "The Ball," 'When We Are Wed," "Promises," and "Wedding Sequence."

91. Ursula [THE LITTLE MERMAID; 2008]

The first of four witches on this list (which means, percentage wise, one out of every 25 great musical theatre characters is a witch; can you guess the other three?). And yes, the mermaid Ariel, Prince Eric, and Sebastian the Crab are all iconic characters, but the one who gets spotlighted on this list is one of the great eely-evil character parts, the lip-licking nasty sea witch, Ursula. Modeled after Divine, Ursula is what you get if you combine Patti LuPone, Phyllis Diller, and a giant octopus flailing her tentacles. It's such a good role that you wonder if they should change the show's title from THE LITTLE MERMAID to THE SCARY SEAWITCH. Key songs featuring the character: "I Want the Good Times Back" (cut from the show), "Daddy's Little Angel," "Poor Unfortunate Souls," and "Poor Unfortunate Souls (Reprise)."

90. Matilda Wormwood [MATILDA THE MUSICAL; 2011]

Meet Matilda, a 5-year-old telekinetic prodigy who helps save a teacher while dealing with her own troubled family and her school's cruel headmistress, Miss Trunchbull. It's a perfect role for a girl whose too young or too small to play little orphan Annie. Key songs featuring the character: "Miracle," "Naughty," "Story 1: Once Upon a Time," "When I Grow Up," "Story 3: The Trick Started Well," "Story 4: I'm Here," "Quiet," and "Revolting Children."

89. Tran Van Dinh, a.k.a. The Engineer [MISS SAIGON; 1989]

The Engineer is a half-Vietnamese/half-French pimp and owner of Dreamland, a scorching Saigon strip club at the end of the Vietnam War. He boasts one of the great show-stopping numbers in the history of musical theatre ("The American Dream"). Key songs featuring the character: "Backstage Dreamland," "The Heat is on in Saigon," "The Transaction," "The Morning of the Dragon," "Back in Town/Coo-Coo Princess," "If You Want to Die in Bed," "Let Me See His Western Nose/Kim and the Engineer," "What a Waste," "Chris is Here," "Paper Dragons," and "The American Dream."

88. Vera Charlies [MAME; 1966]

Mame's loud, theatrical friend, a lush with a knack for a zinger or two (or three). Key songs featuring the character: "It's Today," "The Moon Song (The Man in the Moon)," and one of the all-time great duets, "Bosom Buddies."

87. Joanne [COMPANY; 1970]

Acerbic, rich and saucy (i.e. bitchy) older friend of Bobby's, a vodka stinger always within her grasp. This was Elaine Stritch's iconic role, and it's hard to emerge from the Stritchian or even Luponian shadows with it. But Joanne gets to sing "The Ladies Who Lunch," one of the most famously biting of all Stephen Sondheim songs that will get you to rise to your feet. Key songs featuring the character: "Company," "The Little Things You Do Together," "Side by Side by Side/What Would We Do Without You?", "Poor Baby," and "The Ladies Who Lunch."

86. Amalia Balash [SHE LOVES ME; 1963]

Whip-smart and full of life, Amalia only finds solace writing letters to her secret lonely hearts pen pal. She breaks our hearts with "Will He Like Me?"--a song where a young woman must face her own loneliness, breaking free of her fear and going to meet someone for the first time, someone who she fears may not like her. And when her supposed love does not show at a restaurant, she sings the poignant "Dear Friend." And don't forget her big Act 2 turn, "Vanilla Ice Cream," which is that rare number that is both quirky and iconic. The ending when Amalia and her pen pal, Georg, realize the truth always gets me, no matter how many times I have seen the show (or acted in it or directed it). Key songs featuring the character: "No More Candy," "Three Letters," "I Don't Know His Name," "Will He Like Me?" "Mr. Novack, Will You Please?" "Dear Friend," "Where's My Shoe?" "Vanilla Ice Cream," and "Finale."

85. Beetlejuice [BEETLEJUICE: THE MUSICAL. THE MUSICAL. THE MUSICAL; 2018]

A scheming freaky demon who's invisible to all living individuals unless a mortal says his name three times fast. He's boorish, charismatic, over-the-top without any inhibitions, and audiences love him. (Alex Brightman was perfect in the role.) Key songs featuring the character: "The Whole 'Being Dead' Thing," "Fright of Their Lives," "Invisible (Reprise)/On the Roof," "Say My Name," "That Beautiful Sound," "Good Old Fashioned Wedding," and "Creepy Old Guy."

84. Ado Annie [OKLAHOMA!; 1943]

The boy-crazy Ado Annie flirts her way through the groundbreaking Rodgers and Hammerstein first collaboration. But why the name "Ado Annie"? Officially, it was a name derived after playwright Lynn Riggs' half-aunt, Hannah Ada Riggs. Others think it is a derivation of the words "I do"--"Ado"--which is perfect for a girl who cain't say no. Key songs featuring the character: "I Cain't Say No," "The Farmer and the Cowman," and "All Er Nuthin.'"

83. Betty Rizzo [GREASE; 1972]

The tough, smart-mouthed leader of the Pink Ladies will try anything once...except virginity. Key songs featuring the character: "Summer Nights," "Look at Me, I'm Sandra Dee," "Greased Lightnin' (Reprise)," "We Go Together," and "There Are Worse Things I Could Do."

82. Princess Winnifred the Woebegone [ONCE UPON A MATTRESS; 1959]

Likable, child-like princess from the swamps, comedy gold. Carol Burnett originated the role and became instantly known as one of our country's great comediennes because of it. Key songs featuring the character: "Shy," "The Swamps of Home," "Song of Love," "Happily Ever After," and "Finale."

81. Desiree Armfeldt [A LITTLE NIGHT MUSIC; 1973]

"Isn't it rich?" No longer living the glamorous life, Desiree's a second-rate actress touring small towns and in love with Fredrik. The character is given one of the supreme songs in musical theatre history, a little ditty known as "Send in the Clowns." Key songs featuring the character: "The Glamorous Life," "You Must Meet My Wife," "A Weekend in the Country," "The World Won't End/Every Day a Little Death (Reprise)," and "Send in the Clowns (Reprise)."

80. Angel Dumott Schunard [RENT; 1996]

Fashionable drag queen drummer, Collins' AIDS-stricken lover. Although responsible for a dog's death, he's easily the most adored member of the Alphabet City avant garde, a stylish beacon of love and hope, at one point dressing like Pussy Galore. Key songs featuring the character: "You Okay Honey?" "Today 4 U," "Life Support," "Santa Fe," "I'll Cover You," "Christmas Bells," "La Vie Boheme," "Seasons of Love," and "Contact."

79. Elle Woods [LEGALLY BLONDE; 2007]

Iconic sorority girl/fashionista Elle Woods tackles the snobbery of Harvard Law School and becomes the best lawyer of the bunch. Key songs featuring the character: "Omigod You Guys," "Serious," "What You Want," "Positive," "Chip on My Shoulder," "So Much Better," "Take It Like a Man," "Bend and Snap," "There! Right There!" "Legally Blonde," and "Find My Way/Finale."

78. Alfred P. Doolittle [MY FAIR LADY; 1956]

Eliza Doolittle's Cockney dad, a dustman and drunkard, pure comic relief, especially in his standout, "Get Me to the Church on Time." Key songs featuring the character: "With a Little Bit of Luck" and "Get Me to the Church on Time."

77. Roger Elizabeth De Bris [THE PRODUCERS; 2001]

"The worst director of all time," at least according to Max Bialystock (see below). Colorfully and showily gay, Roger must go onstage as Adolph Hitler in Springtime for Hitler when the lead actor gets injured. And yes, Hitler's never been so flamboyant (then again, as mentioned in the show, the fuhrer's middle name is also "Elizabeth"). Key songs featuring the character: "Keep It Gay," "Act 1 Finale," "You Never Say 'Good Luck' on Opening Night," "Springtime for Hitler," and "Prisoners of Love (Reprise)."

76. The Witch [INTO THE WOODS; 1987]

"I'm not good, I'm not nice, I'm just right." The witch's litany of wants that she gives to the Baker and his wife steers the plot of this, Sondheim's most accessible work. In Act 1, she should be a scary-looking, craggily-skinned creature, sometimes made up to resemble a weathered old lady--Ozzy Osbourne meets The Phantom of the Opera. This makes her mid-stream transformation that much more effective. The witch is all things, part creepy creature, part broken-hearted mother. And she gets to do an early rap to boot! Key songs featuring the character: "Prologue: Into the Woods," "Our Little World," "Stay with Me," "Ever After," "Lament," "Your Fault," the glorious "Last Midnight," and "Finale: Midnight/No One is Alone/Children with Listen/Into the Woods."

75. Audrey II [LITTLE SHOP OF HORRORS; 1982]

Nerdy Seymour loves his flower shop co-worker, Audrey, so much that he names his new plant after her; unfortunately, the plant keeps growing out of control and likes to feast on human beings. Key songs featuring the character: "Feed Me (Git It)," "Coda (Act 1 Finale)," "Suppertime," "Sominex/Suppertime II," and "Finale Ultimo (Don't Feed the Plants)."

74. Che Guevara [EVITA; 1978]

Salty, attitudinal one-man Argentinian Greek Chorus to Eva Peron. The part can be played two different ways: As specifically the real-life Che Guevara, who was from Argentina before becoming a revolutionary guerilla leader elsewhere; or as a sort of Everyman (without using the last name). Either way works. Key songs featuring the character: "Oh What a Circus," "Goodnight and Thank You," "Charity Concert," "Peron's Latest Flame," "A New Argentina," "High Flying Adored," "Rainbow Tour," "And the Monkey Kept Rolling In (And Out)," and "A Waltz for Eva and Che."

73. Miss Agatha Hannigan [ANNIE; 1977]

Runs the Municipal Girl's Orphanage, she's a she-devil who hates children (especially Annie) but loves her alcohol. Key songs featuring the character: "Little Girls," "Easy Street," and "Easy Street (Reprise)."

72. Man in Chair [THE DROWSY CHAPERONE; 1998]

A homebody. Probably the one character on this list with the least amount of songs that he sings (he joins in at the end, and that's about it). That's because he's so busy talking about musicals passionately, especially his favorite, THE DROWSY CHAPERONE. His favorite musical, which comes to life in. his apartment, pulls him out of his slump, his anxiety, the Mean Reds (as opposed to the blues). He carries the show with charisma, intelligence, humor and a quick wit...but not song.

71. The Genie [ALADDIN; 2011]

Freed from his lamp by Aladdin, the Genie is a rabidly rapid speaker, a jokey scene-stealer, a larger-than-life hoot who can rap and scat with the best of 'em. Key songs featuring the character: "Arabian Nights," "Friend Like Me," "Act One Finale," "Somebody's Got Your Back," and "Finale Ultimo: Arabian Nights (Reprise)/A Whole New World (Reprise)."

70. Usnavi de la Vega [IN THE HEIGHTS; 2008]

Owner of the Washington Heights grocery store, De La Vega Bodega, with dreams of moving to the Dominican Republic. Usnavi was named by his parents after one of the first things they saw when they initially arrived in the U.S.: A ship with the words "US Navy" on it. Key songs featuring the character: "In the Heights," "It Won't Be Long Now," "96,000," "The Club," "Blackout," "Hundreds of Stories," "Alabanza," "Champagne," and the beautiful "Finale."

69. Fantine [LES MISERABLES; 1986]

Unemployed, on the street, forced to cut her hair and join a life of prostitution, Fantine's fall from grace would be impossible to watch if it weren't for her striving for some sense of dignity. Her love of her daughter, Cosette, supersedes her own health, her own life. Only death, and the knowledge that her daughter will be taken care of, lets her leave her life of misery. Key songs featuring the character: "At the End of the Day," "I Dreamed a Dream," "Lovely Ladies," "Fantine's Arrest," "Fantine's Death: Come to Me," and "Valjean's Death."

68. Miss Adelaide [GUYS AND DOLLS; 1950]

The spotlighted Hot Box Girl, Miss Adelaide, full of life and vivacity, wants one thing in life: to marry her longtime fiancé, Nathan Detroit. But his inability of actually putting a ring on her finger in marital bliss causes her to have a constant head cold. Key songs featuring the character: "A Bushel and a Peck," "Adelaide's Lament," "Take Back Your Mink," "Adelaide's Second Lament," "Sue Me," and "Marry the Man Today."

67. Anita [WEST SIDE STORY; 1957]

Bernardo's sultry, fiery girlfriend, a Puerto Rican immigrant who likes it hot with her beau whenever he returns from his fights for a "private little mix." She's Maria's confidant, and tries to do her best to help the Marie/Tony relationship until the Jets insult and accost her, and she has a change of heart. "If one of you was lying in the street bleeding," she tells them, "I'd walk by and spit on you." Key songs featuring the character: "Dance in the Gym," "America," "Quintet," and "A Boy Like That/I Have a Love."

66. Quasimodo [THE HUNCHBACK OF NOTRE DAME; 2014]

Deaf due to the bells ringing, hunched and disfigured, the unlikely hero of this story dreams from his bell tower of joining Parisian life. Portraying him takes an actor of great sensitivity, a powerful singing voice and keen physical awareness to capture Quasimodo's disability and heart. Key songs featuring the character: "Sanctuary," "Out There," "Topsy Turvy (Part 1)," "Top of the World," "Heaven's Light," "Esmeralda," "Flight into Egypt," and "Made of Stone."

65. Peter Pan [PETER PAN; 1954]

The show PETER PAN should be as cute as a puppy using a Teddy Bear as a pillow, and the title role should robustly jolt any production to life. Sprightly, energetic, lively, bawdy at times, and flying, the character of Peter Pan is a crowing hoot. Can be portrayed by either a boy or a girl. Key songs featuring the character: "I've Got to Crow," "Neverland," "I'm Flying," Wendy," "I Won't Grow Up," "Mysterious Lady," "Ugg-a-Wugg," "To the Ship," "The Battle," and "Neverland (Reprise)."

64. The Beast [BEAUTY AND THE BEAST; 1994]

Commanding, bigger than life, this is an iconic part that should hover over the rest of cast, a furry Goliath looking like Paul Stanley from KISS meets the Big Bad Wolf. And there must be a connection between him and the Beauty of the title, Belle, or he doesn't belong on this list. Key songs featuring the character: "How Long Must This Go On," "If I Can't Love Her," "Something There," "If I Can't Love Her (Reprise)," and "End Duet/Transformation."

63. Grizabella [CATS; 1982]

Her fur matted, she's homeless and lives in the gutter, a former "Glamour Cat" ostracized by the others. She's picked by Old Deuteronomy for rebirth in the Heaviside Layer (cat heaven); she also boasts Andrew Lloyd Webber's most famous song: "Memory." Key songs featuring the character: "Grizabella: The Glamour Cat," "Memory (Prelude)," "Memory," and "The Journey to the Heaviside Layer."

62. Evan Hansen [DEAR EVAN HANSEN; 2015]

A high school senior with extreme anxiety writes letters to himself, thanks to his therapist, about how each day will be good. Sounds simple, but life always gets in the way. Who can't relate to his gamut of emotions, the total edgy teen experience? Key songs featuring the character: "Waving Through a Window," "For Forever," "If I Could Tell Her," "Disappear," "You Will be Found," "To Break in a Glove," "Good For You," and "Words Fail."

61. Celie [THE COLOR PURPLE; 2005]

This strong, iconic black woman writes letters to God during her struggles of abuse, racism and ultimately hope in the American South during the first half of the 20th Century. Although married, we never learn her last name. Key songs featuring the character: "Somebody Gonna Love You" "Our Prayer," "Dear God - Sofia," "Dear God - Shug," "Uh-Oh," "What About Love?", "The Color Purple," "I Curse You Mister," "Miss Celie's Pants," and "I'm Here."

60. Anna Leonowens [THE KING AND I; 1951]

Strong-willed, intelligent, opinionated, ahead of her time when it comes to breaking societal norms, and extraordinarily passionate; a schoolteacher and widow who meets her match with the King of Siam. Key songs featuring the character: "I Whistle a Happy Tune," "Hello Young Lovers," "Getting to Know You," "Song of the King," and "Shall We Dance?"

59. Billy Elliot [BILLY ELLIOT: THE MUSICAL; 2005]

During hard times (a miner's strike), young Billy secretly practices ballet and turns out to be so talented, he gets to attend the Royal Ballet School in London. In terms of roles, this one's so well-known it could be deemed as Annie for young boys. Key songs featuring the character: "Shine," "Expressing Yourself," "The Letter (Mum's Letter)," "Born to Boogie," "Angry Dance," "Swan Lake," and "Electricity."

58. Michael Dorsey/Dorothy Michaels [TOOTSIE; 2019]

Michael Dorsey can't get work as an actor so he dons drag (as "Dorothy Michaels") and lands a job as Juliet's Nurse in Romeo and Juliet. Whatever misgivings some may have had with the overall musical, one thing was for sure: The part of Michael Dorsey and his female alter ego brought down the house. Key songs featuring the character: "Opening Number," "Whaddya Do," "I Won't Let You Down," "There Was John," "Who Are You?" "Unstoppable," "Talk to Me Dorothy," "Arrivederci," and "Thank You (Talk to Me Dorothy Reprise)."

57. Alison Bechdel [FUN HOME; 2015]

A part so complex it takes three actresses to play her: The Small Alison, aged 10, having to deal with her emotionally lost, closeted father's stridence and also realizing that she is attracted to the same sex; Medium Alison, college age, where she falls in love and comes out of the closet; and Adult Alison, middle-aged, writing her memoir and soaring professionally as a cartoonist and personally as an out lesbian. Key songs featuring the character: "It All Comes Back," "Welcome to Our House on Maple Avenue," "Not Too bad" (Medium Alison), "Come to the Fun Home" (Small Alison), "Helen's Etude," "Party Dress," "Changing My Major" (Medium Alison), "Maps," "Ring of Keys" (Small Alison), "Telephone Wire," and "Flying Away (Finale)."

56. Coalhouse Walker Jr. [RAGTIME; 1996]

A Harlem musician whose life spins downward, from in love with Sarah (singing the remarkable "Wheels of a Dream") to seeking retribution for injustices ranging from a destroyed car to the killing of his beloved. Key songs featuring the character: "His Name Was Coalhouse Walker," "Getting' Ready Rag," "Henry Ford," "The Courtship," "Wheels of a Dream," "Justice," "Coalhouse's Soliloquy," "Coalhouse's Demands," "Sarah's Brown Eyes," "He Wanted to Say," and "Make Them Hear You."

55. Velma Kelly [CHICAGO; 1975]

A sultry killer looking for a partner for her act after she gets out of the slammer; Roxie Hart's murderer's row rival. Key songs featuring the character: "All That Jazz," "Cell Block Tango," "I Can't Do It Alone," "My Own Best Friend," "I Know a Girl," "When Velma Takes the Stand," "Class," and "Nowadays/Hot Honey Rag."

54. Galinda/Glinda the Good Witch [WICKED; 2003]

Perky and showy with a good-witch smile, Glinda gets to be the goody-two-shoes in the Land of Oz, but she also exhibits cunning and even ruthlessness. She certainly knows how to be popular, unlike a certain green-faced witch who shall go nameless (see below). Key songs featuring the character: "No One Mourns the Wicked," "What Is This Feeling," "Dancing Through Life," "Popular," "Defying Gravity," "Thank Goodness," and "For Good."

53. Hedwig Robinson [HEDWIG AND THE ANGRY INCH; 1998]

A genderqueer rocker in concert, the notorious Hedwig suffers a breakdown and in the end strips to her true self in this moving cult musical. There's no part quite like it. Key songs featuring the character: "Take Me Down," "The Origin of Love," "Sugar Daddy," "Angry Inch," "Wig in a Box," "Wicked Little Town," "Hedwig's Lament," and "Midnight Radio."

52. The Leading Player [PIPPIN; 1972]

In some ways, this Greek Chorus (either solo or as a group; I've seen both) is a villain, a master of mischievousness, a cheerleader for artifice. The part's hot for the pageant not the person, the parade not the individual. Friendly at first, the Leading Player becomes more authoritative and bullying as the show goes on, until he or she has had enough and coldly stops all illusions to show the lead character, Pippin, how sad existence is without theatricality. Key songs featuring the character: "Magic to Do," "Glory," "Simple Joys," "Morning Glow," "On the Right Track," and "Finale/Magic Shows and Miracles."

51. Cervantes' Manservant/Sancho Panza [MAN OF LA MANCHA; 1965]

The ultimate sidekick, so lovable, simple, sweet, funny...and grounded. He knows his master is off the wall crazy, but he adores him anyway. Key songs featuring the character: "The Missive," "I Really Like Him," "Golden Helmet of Mambrino," "The Dubbing," "A Little Gossip," and "Man of La Mancha (Reprise)."

50. Charity Hope Valentine [SWEET CHARITY; 1966]

It's no accident that Charity's middle name is "Hope"...she's filled with hope, even after perpetual heartache, even after being pushed in a lake by a thief-boyfriend. This dancer for hire at the Fandango Ballroom in New York City isn't a hopeless romantic; she's a hopeful one. Key songs featuring the character: "You Should See Yourself," "Big Spender," "Charity's Soliloquy," "If My Friends Could See Me Now," "There's Gotta Be Something Better Than This," "I'm the Bravest Individual," "Where Am I Going?" and "I'm a Brass Band."

49. Judas Iscariot [JESUS CHRIST SUPERSTAR; 1970]

The irony of JESUS CHRIST SUPERSTAR is that Jesus is not really the lead character; that honor, for lack of a better word, goes to history's biggest scoundrel, the betrayer of all time, Judas. In this, Judas is a volcanic eruption, a rock star in the making, whose every moment onstage should quake the show to life. Key songs featuring the character: "Heaven on Their Minds," "What's the Buzz/Strange Thing Mystifying," "Everything's Alright," "Damned for All Time/Blood Money," "The Last Supper," "The Arrest," "Judas' Death," and "Superstar."

48. Tracy Turnblad [HAIRSPRAY; 2002]

HAIRSPRAY really lives or dies on its Tracy, the larger-than-life lead character who wants to get on the American Bandstand-like dance sensation, "The Corny Collins Show," and ultimately get the show integrated. Imagine Rosa Parks as a pleasantly plump white girl, a hefty dose of likability, energy and good intentions. Key songs featuring the character: "Good Morning, Baltimore," "Mama, I'm a Big Girl Now," "I Can Hear the Bells," "The Nicest Kids in Town (Reprise)," "Welcome to the '60's," "Big, Blonde and Beautiful," "The Big Dollhouse," "Without Love," and "You Can't Stop the Beat."

47. Frank 'N' Furter [THE ROCKY HORROR SHOW; 1973]

What you get when you merge an alien transvestite, a bisexual mad scientist, a flirty diva, an amoral hedonist, an insane genius, and a charismatic leader...and put them all together in a single persona with fishnet stockings and high heels. Key songs featuring the character: "Sweet Transvestite," "I Can Make You a Man," "Planet Schmanet Janet," "Don't Dream It - Be It," and "I'm Going Home."

46. Ensign Nellie Forbush [SOUTH PACIFIC; 1949]

Yes, this is the one list when the cockeyed optimist Nellie Forbush and flamboyant cross-dressing Frank 'N' Furter stand side by side. (I would love to imagine Nellie's reactions to Frank.) Nellie is the spunky nurse, from Little Rock, Arkansas, in the South pacific during World War II, who almost lets her homegrown bigotry destroy her love of Emile de Becque. Key songs featuring the character: "A Cockeyed Optimist," "Twin Soliloquis," "I'm Gonna Wash That Man Right Outa My Hair," "I'm in Love with a Wonderful Guy," "Honey Bun," "Some Enchanted Evening (Reprise)," and "Finale (Dites-Moi)."

45. Nathan Detroit [GUYS AND DOLLS; 1950]

Another Damon Runyon gambler who manages the oldest established traveling craps game in New York and has been engaged to his sniffling fiancée, Adelaide, for fourteen years. Key songs featuring the character: "The Oldest Established" and "Sue Me."

44. Dr. Henry Jekyll/Mr. Edward Hyde [JEKYLL & HYDE; 1997]

The title part is a dream role, where an actor gets to portray two different roles here, one of them a monstrous murderer, having more sides than Les Miz's Jean Valjean and no Phantom of the Opera mask to cover facial expressions; who wouldn't want to play that? (Although to be fair, both Jean Valjean and the Phantom are so iconic that they score much higher on the list.) Crouching Gollum-like, a hat tipping over his wild eyes, the Mr. Hyde side showcases the euphoria of evil, the deliciousness of devilry. "Confrontation," sung to a reflection in the mirror and over-dramatically giving the actor free reign to chew the stage as both Jekyll and Hyde, is a humdinger; it's as if Jean Valjean keeps turning into the vile Thenardier. Key songs featuring the character: "Lost in the Darkness," "Jekyll's Plea," "Pursue the Truth," "Take Me As I Am," "Here's to the Night (Lucy Meets Jekyll)," "This is the Moment," "Alive," "Obsession," "Dangerous Game," "The Way Back," and "Confrontation."

43. Fanny Brice [FUNNY GIRL; 1964]

Fanny, the real life multi-talented singer-comedienne whose rise to stardom in the early Twentieth century is chronicled in FUNNY GIRL, gets a full character arch, from humble beginnings to headliner with the Ziegfeld Follies. Still, it's hard to imagine this without the first to portray Ms. Brice on Broadway, Barbra Streisand, coming to mind; sorry, but whoever is lucky enough to play Brice will always be compared to the phenomenal Ms. Streisand. Key songs featuring the character: "I'm the Greatest Star," "People," "You Are Woman," "Don't Rain on My Parade," "Sadie, Sadie," "Who are You Now?" and "The Music That Makes Me Dance."

42. Norma Desmond [SUNSET BOULEVARD; 1991]

A lost Old Hollywood viper, vulnerable but ready to strike at a moment's notice. Norma was a silent screen goddess gone mad--Mrs. Bates meets Baby Jane. She knows no real life. Having Norma without her insanity is like having the Hunchback of Notre Dame without a hump or the Phantom of the Opera with no mask. Key songs featuring the character: "Surrender," "With One Look," "Salome," "New Ways to Dream," "The Lady's Paying," "The Perfect Year," "As If We Never Said Goodbye," "A Little Suffering," and "The Greatest Star of All (Reprise)."

41. J. Pierpont Finch [HOW TO SUCCEED IN BUSINESS WITHOUT REALLY TRYING; 1961]

In the early 1960's, J. Pierrepont Finch moves on up the corporate ladder with the aid of a self-help book entitled How to Succeed in Business without Really Trying. Yes, he goes from mere window washer to CEO of the World Wide Wicket Company. Finch is the lead in what could be considered a bouncy musical version of Mad Men, only funnier and with really catchy songs. (In one of Mad Men's brilliant turns, they cast Broadway's original Finch, Robert Morse, in a choice morsel role on the long-running series.) Key songs featuring the character: "How to Succeed," "Company Way," "Been a Long Day," "Grand Old Ivy," "Rosemary," "I Believe in You," and "Brotherhood of Man."

40. Fagin [OLIVER!; 1962]

Aging, sneaky, cowardly, smart, eccentric, and extremely complex, this sly career criminal is the antagonist of OLIVER!...but he should be so charismatic and funny that the audience enjoys his devious acts and may even root for him over the orphan. Key songs featuring the character: "You've Got to Pick a Pocket or Two," "I'd Do Anything," "Be Back Soon," and "Reviewing the Situation."

39. Maria [WEST SIDE STORY; 1957]

A Puerto Rican Juliet, the sister of Shark-leader Bernardo, Maria starts off with a touch of feistiness, wide-eyed innocence and heartfelt, first-love passion when she meets Tony. But she ends up jaded and dark at the end when her world dies around her. Key songs featuring the character: "Tonight," "One Hand, One Heart," "Tonight Quintet," "I Feel Pretty," "Somewhere," and "A Boy Like That/I Have a Love."

38. Bloody Mary [SOUTH PACIFIC; 1949]

A hunched, enterprising Tonkinese during World War II, she banters, barters and trades with the sailors stationed on the nearby islands. She's comic relief, but there's seriousness there, too, especially when it comes to her daughter, Liat. Key songs featuring the character: "Bali Ha'I" and "Happy Talk."

37. Pseudolus [A FUNNY THING HAPPENED ON THE WAY TO THE FORUM; 1962]

The part of this Roman slave was originally written for Phil Silvers but made famous by Zero Mostel in its first incarnation, and later by Whoopi Goldberg and Nathan Lane. Sort of a wise-cracking Roman Bugs Bunny B.C.E. Key songs featuring the character: "Comedy Tonight," "Free," "The House of Marcus Lycus," "Every Little Picture," "Everybody Ought to Have a Maid," "Lovely," and "Funeral Sequence."

36. Professor Henry Higgins [MY FAIR LADY; 1956]

A professor of phonetics, a confirmed bachelor and language snob, he can pinpoint where a person lives based solely on their accent. The recitative songs work for such nose-in-the-air snoot who believes someone with a Cockney accent (like Eliza Doolittle, who will later melt his heart) "has no right to live." Key songs featuring the character: "Why Can't the English?" "I'm an Ordinary Man," "The Rain in Spain," "You Did It," "A Hymn to Him," "Without You," and "I've Grown Accustomed to Her face."

35. Alexander Hamilton [HAMILTON; 2015]

Perhaps Lin-Manuel Miranda's opening lyric describes him best: "How does a bastard, orphan, son of a whore and a/Scotsman, dropped in the middle of a forgotten/Spot in the Caribbean by providence, impoverished, in squalor/Grow up to be a hero and a scholar?" How, indeed. Key songs featuring the character: "Alexander Hamilton," "Aaron Burr, Sir," "My Shot," "The Story of Tonight," "Stay Alive," "Meet Me Inside," "History Has Its Eyes on You," "Yorktown (The World Turned Upside Down)," "Dear Theodosia," "Non-Stop," "One Last Time," "We Know," "Hurricane," "It's Quiet Uptown," "Your Obedient Servant," and "The World Was Wide Enough."

34. Mame Dennis [MAME; 1966]

This title character stands at the forefront of great, strong female characters from classic mid-1960's musicals (labeled "diva vehicles" by some), leading a parade of icons that include Dolly Levi (see below), Fanny Brice (see above) and Charity Hope Valentine (see above). I first saw MAME in 1969 with Edie Adams when I was six, and it has stayed with me ever since. I felt like young Patrick, Mame's nephew, and wanted her to take me around the world. I've always tried to follow Mame's philosophies to "open a new window" and that "life is a banquet and most sons of bitches are starving." She's full of zest, a cheerleader of life. Key songs featuring the character: "It's Today," "Open a New Window," "The Moon Song (The Man in the Moon)," "My Best Girl," "We Need a Little Christmas," "Bosom Buddies," "That's How Young I Feel," and "If He Walked Into My Life."

33. Millie Dillmount [THOROUGHLY MODERN MILLIE; 2002]

Milllie is a young lady from the Midwest looking for love in New York City during the Roaring Twenties. It started off as a so-so 1967 movie starring Julie Andrews and then became a Broadway tap-dancing sensation that turned Sutton Foster into a star in 2002. Her "Gimme Gimme," a diva's belting classic, should cause good bumps while her yearning "Jimmy" should showcase a vulnerability. It's a part that runs the entire emotional gamut. Key songs featuring the character: "Not for the Life of Me," "Thoroughly Modern Millie," "How the Other Half Lives," "The Speed Test," "Jimmy," "Forget About the Boy," "I Turned the Corner/Falling in Love with Someone (Reprise)," and "Gimme Gimme."

32. Roxie Hart [CHICAGO; 1975]

Sultry, salty, and desperately cunning, she's a murderess on trial who looks like a floozy Jean Harlow in her blonde wig, a homicidal Gwen Stefani. And CHICAGO is her town...and her show. Key songs featuring the character: "Funny Honey," "We Both Reached for the Gun," "Roxie," "My Own Best Friend," "Me and My Baby," and "Nowadays/Hot Honey Rag."

30. Nicely-Nicely Johnson [GUYS AND DOLLS; 1950]

Not all of the Top-50 parts are leads; some of the supporting roles steal the show. Which is the case with Nicely-Nicely, the nicest, warmest crooked gambler in New York. Is there a more lovable character in musical theatre? Key songs featuring the character: "Fugue for Tinhorns," "The Oldest Established," "Guys and Dolls," "Luck Be a Lady," and the showstopping "Sit Down, You're Rockin' the Boat."

29. The Baker [INTO THE WOODS; 1986]

He and his wife are outsiders in the story, two people who make a deal with a witch with disastrous results. His post-Ever After story becomes truly heartbreaking. When he sings "No One Is Alone" with Jack, Little Red Ridinghood and Cinderella, the audience's collective tears should flow. In Act 2, he gets to sing some of Stephen Sondheim's loveliest songs (which means some of the loveliest songs ever written). Key songs featuring the character: "Into the Woods," "The Cow as White as Milk," "Maybe They're Magic (Reprise)," "It Takes Two," "Prologue: So Happy," "Your Fault," "No More," and "No One Is Alone."

29. Inspector Javert [LES MISERABLES; 1986]

He represents Old Testament rigid, and he cannot accept the changing world that the New Testament represents. He's an obsessive, and he won't sleep until he gets his fugitive prey...a man named Jean Valjean. Although he considers himself upright and of pure moral fiber-"rules" mean more to him than the human spirit. To be called a "Javert" is not a compliment. Key songs featuring the character (some of the titles are spoilers in and of themselves): "Prologue: Work Song," "Fantine's Arrest," "The Runaway Cart," "Fantine's Death: Come to Me," "The Confrontation," "Javert's Intervention," "Stars," "One Day More," "Building the Barricade (Upon These Stones," "Javert's Arrival," "The First Attack," and "Soliloquy (Javert's Suicide)."

28. Georges Seurat/George [SUNDAY IN THE PARK WITH GEORGE; 1984]

"Are isn't easy." Georges (called George) is exact, obsessed, innovative, a perfectionist, and he sacrifices everything for his pointillist paintings. He also gets the greatest song about creating art in "Finishing the Hat." The second act takes place in modern times, and Seurat's descendant, also called George (played by the same actor), is updated but still as troubled as his ancestor. Key songs featuring the character: "Sunday in the Park with George," "Color and Light," "Finishing the Hat," "We Do Not Belong Together, "Beautiful," "Putting It Together," "Lesson #8," and "Move On."

27. Effie Melody White [DREAMGIRLS; 1981]

Sassy, headstrong, driven, with earned cockiness and supreme talent, Effie is given one of the great belter classics in Broadway history: "And I'm Telling You I'm Not Going." It's an Act 1-closing force, Effie's torchy moment of defiance and Dreamgirls' big number that made a star out of two Jennifers--Holliday and Hudson. Although, to be fair, it's not actually the last song of Act 1; that would be the new Dreams' "Love Love Me Baby." But after the gospel explosions of "And I'm Telling You I'm Not Going," especially in the hands of Jennifer Holliday or Jennifer Hudson, no one would remember anything that follows such greatness. Key songs featuring the character: "Move (You're Steppin' on My Heart)," "Fake Your Way to the Top," "Cadillac Car," "Steppin' to the Bad Side," "Party, Party," "Dreamgirls," "Only the Beginning," "Heavy/Stop Bringing Us Down," "It's All Over," "An I'm Telling You I'm Not Going," "I Am Changing," "One Night Only," and "Listen."

26. Max Bialystock [THE PRODUCERS; 2001]

Max has it all: Dishonesty, desperation, failure, greed, and manipulation. He's also sexually adventurous with little old ladies who financially back his Broadway losers. And with Leo Bloom, he has the ultimate Broadway loser on his hands: "Springtime for Hitler." How could he go wrong, right? Key songs featuring the character: "The King of Broadway," "We can Do It," "Der Guten Tag Hop-Clop," "Keep It Gay," "Along Came Bialy," "Where Did We Go Right?, "Betrayed," "'Til Him," and "Prisoners of Love."

25. Jenna Hutcherson [WAITRESS; 2016]

Big-hearted, witty, knowing, inventive, and slightly timid. A waitress at Joe's Pie Diner, she's a pie-maker par excellence. She also gets to sing the greatest musical theatre song of the last twenty years: "She Used to Be Mine." Key songs featuring the character: "What's Inside," "Opening Up," "The Negative," "What Baking Can Do," "When He Sees Me," "It Only Takes a Taste," "A Soft Place to Land," "Bad Idea," "Dear Baby," "She Used to Be Mine," and "Everything Changes."

24. Jesus Christ [JESUS CHRIST SUPERSTAR; 1970]

When it comes to vocal power, anyone who's portraying JC must pull out his inner Ian Anderson and Ted Neeley, and he must nail each song, each high-pitched rock shriek, each seemingly impossible note. It's a true star turn as we follow His last few days on earth. And is "Gethsemane (I Only Want to Say)" the greatest song Andrew Lloyd Webber ever wrote, or will write? Key songs featuring the character: "What's the Buzz/Strange Thing Mystifying," "Everything's Alright," "Hosanna," "Simon Zealotes/Poor Jerusalem," "The Temple," "The Last Supper," "Gethsemane (I Only Want to Say)," "The Arrest," "Pilate and Christ," "Trial Before Pilate," and "The Crucifixion."

23. King Mongkut, the King of Siam [THE KING AND I; 1952]

He tries to come to terms with the Western world and modern ideas, but there's a struggle when it comes to his old school Eastern values versus the West's. A true leader, with a hidden love for Anna that comes out in the classic duet, "Shall We Dance?" For years, I never thought I could imagine anyone other than Yul Brynner in the role; but then came Ken Watanabe. Key songs featuring the character: "A Puzzlement," "Buddhist Prayer/Act 1 Finale," "Song of the King," and "Shall We Dance?"

22. Annie Oakley [ANNIE GET YOUR GUN; 1946]

Spunky, robust, opinionated, charismatic, competitive, and a bull's eye markswoman. Perhaps the most spirited character on this list. Key songs featuring the character: "Doin' What Comes Natur'lly," "The Girl That I Marry," "You Can't Get a Man with a Gun," "There's No Business Like Show Business," "They Say It's Wonderful," "Moonshine Lullaby," "Adoption Dance," "I Got Lost in His Arms," "I Got the Sun in the Morning," and "Anything You Can Do."

21. Aaron Burr [HAMILTON; 2015]

"Talk less; smile more." Like Judas in JESUS CHRIST SUPERSTAR, Burr is the narrator of HAMILTON, the title character's antagonist and the show's real lead. The two of them are frenemies before the word was ever invented, and historical karma would get Burr in the end when he's the one that fate would choose to kill Hamilton in a duel. Key songs featuring the character: "Alexander Hamilton," "Aaron Burr, Sir," "My Shot," "Right Hand Man," "A Winter's Ball," "Wait For It," "Ten Duel Commandments," "Guns and Ships," "Dear Theodosia," "Non-Stop," "What'd I Miss," "The Room Where It Happens," "Washington on Your Side," "The Adam Administration," "We Know," "The Election of 1800," "Your Obedient Servant," "The World Was Wide Enough," and "Who Lives, Who Dies, Who Tells Your Story."

20. Mrs. Nellie Lovett [SWEENEY TODD: THE DEMON BARBER OF FLEET STREET; 1979]

Ms. Lovett is the brains behind Sweeney Todd's road to revenge. But she goes beyond the goofily awful pie-maker; there's something needy about her, a barrenness that needs to be filled since the death of her husband 17 years earlier. That's why she falls for Sweeney. She's a strong woman, a survivor during hard times, manipulating the key events of the show. And as her name suggests, she loves it. In some ways, she plays Dr. Frankenstein to her monster, Sweeney. Mrs. Lovett is a vile creation, perhaps the devil incarnate (it's alluded to several times in the show and her hair even appears to sprout horns), but she's so entertaining and laugh-out-loud funny that you forgive any and all of her putridness. Key songs featuring the character: "The Worst Pies in London," "Poor Thing," "My Friends," "Pirelli's Miracle Elixir," "Wait," "A Little Priest," "God, That's Good," "By the Sea," "Not While I'm Around," "Parlour Songs," "City on Fire," and the final "Ballad of Sweeney Todd."

19. Sally Bowles [CABARET; 1966]

The star of the Kit Kat Club in 1930's Berlin, Sally doesn't understand the irony when she tells her lover, Cliff Bradshaw, that he's too innocent. She doesn't realize that she's the innocent one, clueless. When she states that politics has no effect on them, we know how wrong she is (we know what the goose-stepping future will hold). And she also sings what we picked as the #1 show tune of all time: "Cabaret." The key to the song is that it is pregnant Sally's unapologetic epiphany--she wants an abortion in order to free herself of any responsibilities. The world may be changing around her, but she's clueless to that; she just wants to sing, drink and have as many sexual encounters as she can. And in the end, she would rather entertain a room filled with Nazis than live a normal life. Key songs featuring the character: "Don't Tell Mama," "Mein Herr," "Perfectly Marvelous," "Money," "Maybe This Time," and "Cabaret."

18. Billy Bigalow [CAROUSEL]

Time magazine once called CAROUSEL the greatest musical of the 20th Century. And Billy is one of the greatest characters. A Mullin Carousel barker, a rogue and ladies' man, he turns to a life of crime in order to help his family. Events end up tragically, and Billy tries to find a way to make things right, even from the Hereafter. Key songs featuring the character: "If I Loved You," "Blow High, Blow Low," "Soliloquy," and "The Highest Judge of All."

17. Eliza Doolittle [MY FAIR LADY]

A low class flower girl on the street from Lisson Grove, who, according to Henry Higgins, is a "gutter snipe." With the help of the professor, she transforms into a graceful, polished, self-determining young lady. "Loverly" as she would have said prior to the change. The name "Eliza Doolittle" has come to epitomize the Cockney accent (be honest; when you hear the word Cockney, you immediately think of her, don't you?). Key songs featuring the character: "Wouldn't It Be Loverly," "Just You Wait," "The Rain in Spain," "I Could Have Danced All Night," "Show Me," "The Flower Market/Wouldn't It Be Loverly," and "Without You."

16. The Phantom [THE PHANTOM OF THE OPERA; 1986]

"Nighttime sharpens, heightens each sensation/Darkness stirs and wakes imagination...". The mysterious figure, his facial deformity hidden behind a half-mask, lives in an underground lair underneath the Paris Opera House and is obsessed with Christine, his muse. Is there a more iconic image than the Phantom's mask? Key songs featuring the character: "The Phantom of the Opera," "The Music of the Night," "I Remember.../Stranger Than You Dreamt It," "All I Ask of You (Reprise)," "Why So Silent," "Wandering Child/Bravo, Monsieur," "The Point of No Return," and "Down Once More/Track Down This Murderer."

15. Maria Von Trapp [THE SOUND OF MUSIC; 1959]

Robust and full of verve, overzealous in an "Up with People" kind of way, this nun-turned-nanny-turned-wife is strong, scrappy and spunky, bursting with energy. We love watching her and listening to her incredible voice in such standards as "The Sound of Music," "My Favorite Things," and her various numbers with the von Trapp children. The songs are so familiar that the whole musical sounds like Rodgers & Hammerstein's Greatest Hits. Key songs featuring the character: "The Sound of Music," "My Favorite Things," "Do-Re-Mi," "The Loney Goatherd," "An Ordinary Couple," "Edelweiss," "So Long, Farewell (Reprise)," and "Finale Ultimo."

14. Bobby [COMPANY; 1970]

Bobby, COMPANY'S semi-narrator, is a 35-year-old bachelor who isn't ready for emotional commitment with anybody. It's his birthday, and the musical opens in his NYC apartment, with his married friends present, and he's ready to blow out the candles on his birthday cake. We suddenly see his life in fragments, his life with each couple, with each girlfriend. It's very funny and poignant, and it still emotionally punches you as if it had been written yesterday, not during the era of Richard Nixon and Talking Viewmasters. Bobby is without question one of the hardest characters in musical theatre to capture, to play correctly--mixing his laissez faire attitude with the ability to drive the story. Unlike Sweeney, he has no bombast, no moments of sweat, no real motivation (imagine Sweeney without the need for revenge). He's not just a blank page; he's a blank book. Yet, he ranks rather high on this list. Because, cypher that he is, he's iconic, so open that he can be played by either a man, or as seen in the recent re-imagining, a woman. And he sings one of the greatest songs to ever grace a musical: "Being Alive." Key songs featuring the character: "Company," "Someone Is Waiting," "Marry Me a Little," "Side by Side by Side/What Would We Do Without You," "Barcelona," and "Being Alive."

13. Tevye the Dairyman [FIDDLER ON THE ROOF; 1964]

Tevye is one of the most entertaining, likable lead characters in any musical. A poor, pious villager who can only dream of wealth, he tries to keep his Jewish traditions but the outside world keeps interfering with his family. But audiences love him, and he is the main reason that this musical endures in community and high school theaters the world over. Key songs featuring the character: "Prologue: Tradition," "If I Were a Rich Man," "Sabbath Prayer," "To Life," "Tebye's Monologue," "Teyve's Dream," "Sunrise, Sunset," "Teyve's Rebuttal," "Do You Love Me?," and "Chavaleh (Little Bird)."

12. Diana Goodman [NEXT TO NORMAL; 2008]

The bipolar-stricken Diana is a part any actress worth her salt would kill for (originally made famous by Alice Ripley). We feel for her, understand her struggle, and buy in to her story. Some of her songs, especially "I Miss the Mountains," her part of "The Song of Forgetting" and "The Break," leaves audiences breathless, unsure whether to applaud or weep. Key songs featuring the character: "Preprise - Let There Be Light," "Just Another Day," More...And More...And More," "I Miss the Mountains," "It's Gonna Be Good," "You Don't Know," "Superboy and the invisible Girl," "I Dreamed a Dance," "Didn't I See This Movie?" "A Light in the Dark," "Feeling Electric," "Song of Forgetting," "Getting Better," "Better Than Before," "How Could I Ever Forget," "Everything," "The Break," "Make Up Your Mind/Catch Me I'm Falling," "Maybe (Next to Normal)," "So Anyway," and "Finale (Let There Be Light)."

11. Albin [LA CAGE AUX FOLLES; 1983]

If done right, Albin's Act 1 ending anthem, "I Am What I Am," will move you, shake you, chill you and thrill you. Albin, the hysterical drag performer, sings it in response to learning that the straight son he has helped raise needs to deny his existence in order to impress the staunch anti-gay conservative parents of the son's fiancée. Albin is often hilarious, sad at times, but always in love with his husband, Georges, and always someone for the audience to cheer. Key songs featuring the character: "(A Little More) Mascara," "With You on My Arm," "La Cage Aux Folles," "I Am What I Am," "Song in the Sand (Reprise)," "Masculinity," and "The Best of Times."

10. Annie [ANNIE; 1977]

Perky, optimistic orphan who's a thorn in Miss Hannigan's side and heart-warmer for the wealthy titan, Daddy Warbucks, who will adopt her. At 11, she is the ultimate role for a girl, and I even wrote a play about young ladies fighting almost to the death for the star part ("Every Girl Wants to Be Annie"). Is there a more optimistic ode for the future than "Tomorrow"? Key songs featuring the character: "Maybe," "It's a Hard Knock Life," "Tomorrow," "I Think I'm Gonna Like It Here," "N.Y.C.," "Tomorrow (Cabinet Reprise)," "I Don't Need Anything But You," and "A New Deal for Christmas."

9. The Emcee (Master of Ceremonies) [CABARET; 1966]

"Is it a crime to fall in love? Can we ever tell where the heart truly leads us? All we are asking is eine bisschen Verstandnis...Why can't the world leben und leben lassen? Live and let live..." (from "If You Could See Her," sung by the Master of Ceremonies to a Gorilla in CABARET). It's the 1930's, and the giddily devilish Emcee welcomes us to the Kit Kat Club as the show opens. The part, made famous in the 1960's by Joel Grey and in the 1990's by Alan Cumming, is a mercurial figure, frightening and entertaining. He can be almost serpent-like as he roams this club in Berlin (or is it Hades?), his lithe hands rubbing all over this club of unclad loose women and drag queens. And as the story sadly moves forward into the horrors of Nazi Germany, he transforms as well. If the Emcee doesn't work, you have no show. Key songs featuring the character: "Wilkommen," "Two Ladies," "Sitting Pretty," "Money," "Kickline," "If You Could See Her," and the haunting "I Don't Care Much."

8. Elphaba, the Wicked Witch of the West [WICKED; 2003]

Who ever thought the Wicked Witch of the West could ever be a protagonist? With her green skin, she suffers quite a bit of shame from others, but can bounce back with abandon. Intelligent, passionate, she has a keen understanding and empathy for the outsiders of the world, but her magic becomes a twister-like force. She is hands down the single greatest role of the 2000's, and with "Defying Gravity," is given one of the world's great, literally uplifting numbers as she flies on her broom. Key songs featuring the character: "The Wizard and I," "What is This Feeling," "Something Bad," "I'm Not That Girl," "One Short Day," "Defying Gravity," "The Wicked Witch of the East," "As Long As You're Mine," "No Good Deed," "Wonderful," and "For Good."

7. Professor Harold Hill [THE MUSIC MAN; 1957]

The charismatic con-artist/salesman awakens a sleepy Midwest town. Harold's the pied piper of the performing arts, a Johnny Appleseed selling hopes and dreams to a dead-end town that needs it. And if your Harold Hill doesn't cut it, if he doesn't knock your socks off with his charisma, then you got more trouble than anything in River City. Key songs featuring the character: "(Ya Got) Trouble," "Seventy-Six Trombones," "The Sadder-But-Wiser Girl," "Marian the Librarian," and "Till There Was You (Reprise)."

6. Miguel de Cervantes/Don Quixote [MAN OF LA MANCHA; 1965]

Cervantes/Quixote is one of the theatre's powerful, awe-inspiring roles. The transformation from Cervantes to the bearded Quixote should be one of the spellbinding moments. And the rousing "Man of La Mancha (I, Don Quixote)" is always sensationally stirring. But the show ultimately stops when Quixote sings "The Impossible Dream," one of the great songs in musical theatre history. Here it is, everything we look for in theatre--thrilling, spine-tingling, goose bump-inducing and tear-duct-tugging. And when done right, the audience doesn't want to stop their applause afterwards. Key songs featuring the character: "Man of La Mancha (I, Don Quixote)," "Dulcinea," "Golden Helmet of Mambrino," and "The Impossible Dream."

5. Eva Peron [EVITA; 1979]

The stunning first lady of Argentina had her moments and she had some style but she died way too young. Her signature tune, "Don't Cry for Me, Argentina," should be a rafter-shaker. Evita exudes the sort of cunning that you can see in Barbara Stanwyck in Double Indemnity, the glamor of Anita Ekberg in La Dolce Vita, all mixed with First Lady Melania Trump but with more power. The part needs that extra spark of star quality, plus a powerful voice; it's a belter's dream role. Key songs featuring the character: "Eva and Magaldi/Eva Beware of the City," "Buenos Aires," "Goodnight and Thank You," "I'd Be Surprisingly Good for You," "Hello and Goodbye," "Peron's Latest Flame," "A New Argentina," "On the Balcony of the Casa Rosada," "Don't Cry for Me Argentina," "High Flying Adored," "Rainbow High," "The Actress Hasn't Learned the Lines (You'd Like to Hear)," "A Waltz for Eva and Che," "You Must Love Me," "Dice are Rolling/Eva's Sonnet," "Eva's Final Broadcast," "Montage," and "Lament."

4. Jean Valjean/Prisoner 24601/ Monsieur Madeleine [LES MISERABLES; 1986]

Jean Valjean is God's messenger of hope and redemption in troubled times. A convict turned hero, a man who does the right thing, saving lives and saving souls. "Bring Him Home" is his show-stopper (it has always been one of the most beautiful numbers in musical theater history), and his last scene, as an old man letting go of his secrets, will break your heart. Redemption: My favorite theme. Key songs featuring the character: "Prologue: Work Song/On Parole/Valjean Arrested, Valjean Forgiven/What Have I Done," "At the End of the Day," "Fantine's Arrest," "The Runaway Cart," "Who Am I? (The Trial)," "Fantine's Death: Come to Me," "The Confrontation," "The Bargain/The Thenardier Waltz of Treachery," "The Robbery," "The Attack on the Rue Plumet," "One Day More," "The First Attack," "Bring Him Home," "Every Day," "Valjean's Confession," and "Valjean's Death."

3. Dolly Gallagher Levi [HELLO DOLLY; 1964]

A widow with her best years behind her, she becomes a matchmaker for everyone else. Dynamic, caring, pushy, but charismatic and crazily energetic, she's the definition of a busybody. And so much fun to watch. Key songs featuring the character: "I Put My Hand In," "World, Take Me Back," "Before the Parade Passes By," "Hello, Dolly," and "So Long, Dearie."

2. Sweeney Todd [SWEENEY TODD: THE DEMON BARBER OF FLEET STREET; 1979]

Sweeney's song "My Friends," the murderous barber's ode to his razors, is one of the greatest love songs Sondheim ever wrote. And Sweeney is handed the finest trifecta of songs in any show--"Pretty Women," followed by the chilling "Epiphany," followed by the show's standout number, "A Little Priest." And we root for Sweeney, even when his specific revenge moves to the general populace, even as he slits throats and, at the same time, sings longingly of his daughter. You sense a rabid joy in Sweeney, an artist with a knife finally finding his tools, his voice, when he discovers the art of murder. At the end of the show, when he pushes his revenge one throat too many, his tragedy becomes our tragedy. Key songs featuring the character: "The Ballad of Sweeney Todd," "No Place Like London," "Barber and His Wife," "My Friends," "Pirelli's Mircle Elixir," "The Contest," "Pretty Women," "Epiphany," "A Little Priest," "God, That's Good," "Johanna," "Wigmaker Sequence," "The Letter," and "City on Fire/Searching."

And the number one character/role in a musical is...

1. Rose [GYPSY; 1959]

You know her better as "Mama Rose," but she's never officially called that in the musical (she is referred to as "Madame Rose" or "Mama," but never "Mama Rose"). She's the ultimate stage parent, the biggest mother of them all ("Mommie Dearest," move over). Pushy and smart, a locomotive of sorts, you better move out of her way if you see her coming. Overbearing yet charming, a dictator in a skirt, forcing optimism even when it's not there ("Everything's Coming Up Roses"), she always lands on her feet, a true survivor. She even gets her moment in the spotlight with the show-stopper, "Rose's Turn," where she's coming apart due to her "ungrateful" children. Bette Midler was right when she called it "a terrifying piece of music." "Terrifying" - also a great way to describe the demanding, domineering, taxing and formidable Rose--the greatest musical theatre role of all time. Key songs featuring the character: "Some People," "Small World," "Have an Eggroll, Mr. Goldstone," "You'll Never Get Away from Me," "Everything's Coming Up Roses," "Madame Rose's Toreadorables," "Together, Wherever We Go," and the incomparable "Rose's Turn."


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From This Author Peter Nason