It's not Broadway, but when the Roundabout revived Tennessee Williams's THE MILK TRAIN DOESN'T STOP HERE in 2011, a male actor (Edward Hibbert) played The Witch of Capri, a traditionally female role.
An older example is the play WHOSE LIFE IS IT ANYWAY?, which opened on Broadway with a male actor (Tom Conti) in the leading role. The part was then rewritten to allow Mary Tyler Moore to replace him. The play now essentially exists in two versions -- one with a male main character and one with a female main character -- and has been revived for both men and women.
"You travel alone because other people are only there to remind you how much that hook hurts that we all bit down on. Wait for that one day we can bite free and get back out there in space where we belong, sail back over water, over skies, into space, the hook finally out of our mouths and we wander back out there in space spawning to other planets never to return hurrah to earth and we'll look back and can't even see these lives here anymore. Only the taste of blood to remind us we ever existed. The earth is small. We're gone. We're dead. We're safe."
-John Guare, Landscape of the Body
Let's not forget Neil Simon famously reworked The Odd Couple to have it star Rita Moreno and Sally Struthers as Olive and Florence, and have the Pigeon Sisters become the Costazuela Brothers.
"Ok ok ok ok ok ok ok. Have you guys heard about fidget spinners!?" ~Patti LuPone
I guess the Company revival doesn’t STRICTLY count because the text was actually changed to switch the sex of the character, but I guess it kind of counts.
"You can't overrate Bernadette Peters. She is such a genius. There's a moment in "Too Many Mornings" and Bernadette doing 'I wore green the last time' - It's a voice that is just already given up - it is so sorrowful. Tragic. You can see from that moment the show is going to be headed into such dark territory and it hinges on this tiny throwaway moment of the voice." - Ben Brantley (2022)
"Bernadette's whole, stunning performance [as Rose in Gypsy] galvanized the actors capable of letting loose with her. Bernadette's Rose did take its rightful place, but too late, and unseen by too many who should have seen it" Arthur Laurents (2009)
"Sondheim's own favorite star performances? [Bernadette] Peters in ''Sunday in the Park,'' Lansbury in ''Sweeney Todd'' and ''obviously, Ethel was thrilling in 'Gypsy.'' Nytimes, 2000
There are not that many examples here. However, there seems to be more in the UK. Recently, Joanna Ampil as the engineer in Miss Saigon, and there have been a few Miss Hannigans played by Drag Performers as women. In emergencies here, there have been some times males have gone on in female roles. In the revival of Cats, Corey Snide went on for JennyAnyDots, and in Hadestown, males have gone on as the Fates. Titus Burgess played the Witch in Into the Woods, I believe in Florida somewhere (though I am not sure if he played it as a Witch or a Warlock).
Generally, license companies for musicals are quite protective of their shows. For example, I know there was a theater that wanted to have in their production of Little Shop, Mr. Mushnik become Mrs. Mushnik with a celebrity in the role. But that request was denied.
The late 90s revival of Grease we saw Darlene Love, Mary Bond Davis, and Jennifer Holiday as the Teen Angel singing Beauty School Dropout.
Rosie O'Donnell and Cathy Rigby played the Cat in the Hat in Seussical after the role being originated by a man.
Melissa Etheridge played St. Jimmy in American Idiot.
Also the role of Papa Ge in the Once on This Island revival was cast as a woman instead of the traditional man - though a man did also understudy the role.
Didn't Waitress have a stunt cast for the role of Joe that was a woman? I remember hearing they changed the lines about losing the baby when Joe is reminiscing.
On another note: I've seen a couple of local productions of Guys and Dolls where Arvide Abernathy is a female character. I also recently saw a local production of Anything Goes where Moonface Martin is a woman, who instead disguises herself as a nun (and gets the girl in the end).
Kitsune said: "Didn't Waitress have a stunt cast for the role of Joe that was a woman? I remember hearing they changed the lines about losing the baby when Joe is reminiscing.
June Squibb played the role, but it was renamed "Josie," and the character was explicitly a woman.
This didn't actually happen because 9/11 happened first so producers became much more cautious of how they'd spend money, but if I recall correctly Billy Porter was slated to play the Witch in the 2002 Into the Woods revival.
Someone pointed out that Lena Hall played Hedwig - which is true, and it reminded me that Ally Sheedy was the first woman to play Hedwig, back in its original Off-Broadway run.
helvizz said: "This didn't actually happen because 9/11 happened first so producers became much more cautious of how they'd spend money, but if I recall correctly Billy Porter was slated to play the Witch in the 2002 Into the Woods revival.
Someone pointed out that Lena Hall played Hedwig - which is true, and it reminded me that Ally Sheedy was the first woman to play Hedwig, back in its original Off-Broadway run.
"
I love your profile picture-- Harvey is my favorite
Also I have known almost all of these but I gotta say I did not know about Ally Sheedy