The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON

Jonah Jackson Directs, With Musical Direction by Randy Craft, The Latest Musical Offering at The Barbershop Theatre

By: Mar. 08, 2024
The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON
Enter Your Email to Unlock This Article

Plus, get the best of BroadwayWorld delivered to your inbox, and unlimited access to our editorial content across the globe.

Existing user? Just click login.

Jonah Jackson directs The Trail to Oregon, with musical direction by Randy Craft – the latest musical from Nashville’s Street Theatre Company, opening tonight and running through March 23 at The Barbershop Theatre, 4003 Indiana Avenue.

Originally written and produced by Team Starkid (of A Very Potter Musical fame), The Trail to Oregon! parodies the video game The Oregon Trail, which follows a pioneer family on their journey westward to make a new life for themselves. Described as “hilarious and ‘edu-macational’ musical comedy,” the audience chooses the characters’ names at each show and making the decision of which family member succumbs to dysentery on the way to the Pacific Northwest.

The cast features First Night Award winners Ben Friesen and Jennifer Whitcomb-Oliva (who plays Grandpa), along with Kristen Fields, Eve Petty, Taryn Pray and Elijah Wallace.

In today’s Friday Five (+1), Friesen, Fields, Petty, Pray and Wallace respond to our usual questions and suggest why you need to come see their show – and who knew how important eighth grade experiences can be?

Tickets are already scarcer than potable drinking water on a cross-country trek, but you can get more details at!

The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON Kristen Fields (Mother)

What was your first "live, onstage" taste of theater? One of our eight grade field trips was a visit to whatever high school we'd be attending in the fall, which included a presentation by the arts programs to entice us to join. They performed “One Day More” from Les Miserables, and I think my soul left my body for a few moments. I signed up for my first-ever acting class that day.

What is your favorite pre-show ritual? I love taking a big deep breath right before curtain and reminding myself how lucky I am to be there and to let everything else go and just be present. 

What's your most memorable "the show must go on" moment? I was Audrey in Little Shop long before I understood that a wig needed to be kept in place with multiple hairpins throughout. When I'm *spoiler alert* eaten by the plant the first time, my wig fell clean off my head into the depths of Audrey II. I somehow managed to get it back on my head with my legs still flailing out of its mouth before I'm pulled out by Seymour. Was it on the right way? I'm not sure – I think I blacked out. But the show did indeed go on.

What's your dream role? I have yet to do any Sondheim, and would love to tackle almost any of his work.

Who's your theatrical crush? She's made her way to our hearts on TV in Ted Lasso, but Hannah Waddingham is one of those performers I'd watch forever and ever. She straddles strength, humor and vulnerability so well.
Why should people come see Trail to Oregon? For a little bit of nostalgia, a lot of laughs, and a few numbers that might make you say, "Well, I never thought I'd see that on stage, but I'm weirdly glad I did."

The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON Ben Friesen (Father)

What was your first "live, onstage" taste of theater? When I was in first grade, my parents surprised me and my older brother by pulling us out of school to go downtown Chicago to see Wicked—there’s nothing more exciting to a seven-year-old! We spent the rest of our childhood singing along to the CD in the car, laughing as my dad sang Glinda’s operatic soprano notes in the opening number. My brother Noah and I also turned out to be a perfect fit for Elphaba and Glinda, respectively, in “What is This Feeling”!

What is your favorite pre-show ritual?  It definitely varies from show to show, but it always includes cracking as many body parts as I can, stretching, and praying before stepping onstage.

What's your most memorable "the show must go on" moment? When I was in eighth grade, I played Sherlock Holmes opposite my middle school girlfriend as my love interest, Shirley. At the end of the show, there was this super cheesy ‘repeat each other’s names as you step closer together’ moment that was supposed to be interrupted by Maggie Baskerville just before we would kiss…but Maggie Baskerville missed her cue. So there I was, standing in front of my family, my girlfriend’s family, and all of our friends, about to have my first kiss in front of hundreds of people. Instead, I started improvising as though Sherlock himself was trying to avoid the kiss, which was met with raucous laughter and our two very red faces until Miss Baskerville finally decided to show up.

What's your dream role? I really want to play Orpheus in Hadestown! He’s a dreamer and a musician, and his resilience and determination in pursuit of Eurydice is so sweet, powerful, and true to life. I got to play him for a collection of scenes from Hadestown when I was at the National Theater Institute, and that was a huge highlight for me. I love “seeing the world the way it could be, in spite of the way that it is.”

Who's your theatrical crush? Appropriately, Eva Noblezada (who played Eurydice in Hadestown). I had the honor of doing a masterclass with her in 2020, and she was so delightful and bubbly and supportive…and man, can she sing. I’ve gotta find a way to see her and Jeremy Jordan (because what tenor doesn’t have a theatrical crush on him) in the new Gatsby musical on Broadway!

Why should people come see Trail to Oregon? This is truly one of the funniest shows of all time, and probably the most fun show I’ve ever been a part of. I’ve loved it since I started watching Starkid’s productions on YouTube in high school, and it’s such a dream come true to be a part of one! If you see me with a straight face at any point in this show (especially that one scene with Grandpa in Act Two), just know that it’s taking everything within me to not burst out laughing at any moment.

The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON Eve Petty (Daughter)

What was your first "live, onstage" taste of theater? I saw Suessical at Nashville Children’s Theatre when I was in elementary school. And now I’ve worked there as both an actor and teaching artist, a true full-circle moment. 

What is your favorite pre-show ritual? I like to do a physical warm-up on the stage; it helps me transition into the space both physically and mentally. Plus, I like to drink a cup of tea and set some specific intentions for the show. 

What's your most memorable "the show must go on" moment? When I was playing Rizzo in my high school’s production of Grease, Sandy accidentally slapped me straight across the face during a performance. We were both shocked for a moment, as you can imagine, but just kept going with the scene. And now I teach fight choreography to high school students so that experience doesn’t happen to them. 

What's your dream role? My dream is to combine my love for acting and sword fighting in plays, musicals, and performance art. A role like Joan of Arc or Boudica would fulfill that, but I want to create more space for modernized fight-works as well.

Who's your theatrical crush? Andrew Scott and Phoebe Waller-Bridge! I am obsessed with Fleabag; I think Phoebe is a genius writer. And nobody gets me to watch and understand Shakespeare and other classical works like Andrew. 

Why should people come see Trail to Oregon? I have loved StarKid musicals since I was in high school, and I can’t believe I get to perform in one now and share Trail to Oregon with Nashville audiences. Come see this cast of hilarious actors fulfill their theatre nerd dreams and have the best time doing it. 

The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON Taryn Pray (Son)

What was your first "live, onstage" taste of theater? I saw Les Mis on Broadway when I was eight years old. I had spent hours upon hours listening to the cassette tape soundtrack in my living room, reading all the liner notes and memorizing all the lyrics. Getting to see it live started it all for me!

What is your favorite pre-show ritual? I always find at least one song or I’ll put together a playlist that gets me in the right headspace for whatever character I’m playing, that I will listen to while getting ready for the show. Also, I need to do a hands-in with the entire cast before we go on. I’m very superstitious about it!

What's your most memorable "the show must go on" moment? I played Rapunzel in Into the Woods when I was a freshman in high school. I had on a 40-pound wig, with one lone Velcro-d hair strand that the Baker’s Wife could easily pull. I had to be strategic when “letting my hair down” to make sure this piece was easy for her to find – which stressed me out every night! One time, it didn’t fall exactly right, and she ended up pulling out like 5 hairs from the wig that weren’t supposed to come out. You could barely see it from stage but she made it work!

What's your dream role? I’m a Sondheim die-hard – if I could play Mrs. Lovett, Dot or Cinderella at some point in my life, I would be in heaven.

Who's your theatrical crush? Bernadette Peters. I have seen her perform live twice and she’s incredible to watch. I could listen to her sing the phone book.

Why should people come see Trail to Oregon? This is truly unlike any show I have ever seen!  It is so funny and the cast is hilarious, so it’s a challenge for all of us not to break on stage. I love that we have the opportunity to improv and that the audience gets to be involved. They choose our names (which we then have to remember throughout the show), and they decide which one of us dies of dysentery. No two shows will ever be the same!

The Friday Five (+1): The Cast of Street Theatre Company's THE TRAIL TO OREGON Elijah Wallace (Everyone Else)

What was your first "live, onstage" taste of theater? For me it is hard to place! I had been seeing shows and around theater since I was a baby because that was what my dad did for work. The first ever show I took part in was The Wizard of Oz. I was barely 5 and a half but I was boldly instructed to be a chief member of the lollipop guild. My dad directed and said we could be as crazy as we wanted for the flying monkey scene as long as we were good as gold as the lollipop guild. It worked like a charm because I got to throw hay around the stage and howl like a monkey. Some things never change I guess.

What is your favorite pre-show ritual? For me it is pretty simple. I like to try and find a quiet spot and stay still for a few moments with my eyes closed. Half-meditation and half-centering myself for the show ahead of me. That and maybe a pre-show mint or two.

What's your most memorable "the show must go on" moment? When I was 12 years old I was involved in a production of Scrooge the musical. I was Young Scrooge, but for this tale my other role of Street Urchin is the important one. I had gotten a pretty rough flu like cold during the show run, and I was running on dayquil and cough drops so I could have a voice at all. Right before the scene where the procession with Scrooge and co goes and buys a turkey and toys and things I felt perfectly fine. Then, as the stage lights hit me something changed. I saw spots dancing in front of my eyes, I started to feel very faint. The moment I knew I was fading fast was when I dropped the massive papier mache turkey I was holding to the ground, and I saw the Mrs. Cratchitt actor follow the descent, then look at me with intense worry. I made it offstage at my normal exit, then promptly passed out offstage. Success! I had not passed out onstage!

What's your dream role? I would love to play Jean Valjean when I am a bit older, but right now I would like to take a stab at Jekyll and Hyde.

Who's your theatrical crush? That is a tough one. I respect a lot of artists out there but having just one is hard to pick. All of them is my final answer.

Why should people come see Trail to Oregon? If you want to spend an hour-and-a-half laughing and forgetting all the crazy stuff out in the world then you should come see this show. It is hilarious, I play like 10 characters, there’s interactive elements with the audience, and somebody dies of dysentery. It's gonna be a great time!

photos by Andrew Morton