Exclusive: From Swing to Full-Time Principal, Derek Jordan Taylor Makes THE OUTSIDERS Role His Own

Derek Jordan Taylor had a busy first week in his new position. After assuming the role of Two-Bit full-time on October 13 in the Broadway musical The Outsiders, he was already on a few times as understudy for Dallas Winston — but being a former swing, he’s used to it. 

“I’m not even at my dressing room station that I’ve set up,” Taylor exclusively tells BroadwayWorld, adding that he’s still coming to terms with the fact that the part of Two-Bit is officially his for the foreseeable future. 

Taylor joined the cast of the Tony Award-winning musical earlier this year, when he was hired as a swing, covering the roles of Two-Bit, Dallas, Steve and Ace before it was announced that original cast member Daryl Tofa was leaving and Taylor would be stepping into the role of Two-Bit permanently. 

“I’m stoked to be able to take over and just be in one [track] every night,” he admits. “There’s always some weight off your back when you don’t have to have that swing brain anymore.” 

Learning multiple roles could be challenging for any performer, but Taylor has gotten used to it. The actor was studying at Boston Conservatory at Berklee when he left school to make his Broadway debut as a swing in the 2022 revival of Funny Girl. 

Though Taylor was grateful for the opportunity to “touch several different parts of the show” with Funny Girl, he says, he was also ready to take on roles that allowed him to be on stage at every performance. 

Taylor went on to ensemble roles in Boop! The Musical and The Great Gatsby, and though he didn’t intend to go back to swinging, the chance to join The Outsiders was too good of an opportunity to pass up. 

“I sat with myself for a second, and I was like, ‘Do you want to be a part of this? Don’t you want to feel what that rain feels like?’” he recalls. “And I was like, ‘Yeah, I do.’”

Taylor was guaranteed a four-week stint as Two-Bit when he signed onto the show due to Tofa’s scheduled leave, but he didn’t know that eventually playing the role full-time was actually in the cards. 

“My headshot moving from the ensemble page to the principal page was just a really special and exciting step, I feel like, in my career,” Taylor says. “I love being on stage; being offstage is tough.” 

While being a swing can be thrilling and keeps a performer on their toes, there’s also something special about settling into a role and forming a new dynamic with the ensemble of actors at the theater each night. 

“When I’m a swing, I enter, I go upstairs, I have my people that I see, and then I leave during the show. I think everyone’s really excited to just be able to spend more time with me,” Taylor says. “I’m super excited to spend more time with them, and they’ve all been supportive of having me there.” 

Taylor explains that his “day-to-day schedule outside of” Broadway’s Bernard B. Jacobs Theatre has changed as well. 

“Not knowing what your night is going to look like is hard to plan exercise and seeing friends and eating,” he says. “So that’s something that I’ve really come to appreciate being full-time — the sense of knowing what your week is going to look like. There’s absolutely a sense of relief. I’m also on my phone way less. I’m not waiting for that message from my stage manager.” 

Though Taylor has only started to settle into his new position at The Outsiders, he’s already “figuring out” how to make the role his own while still “honoring what [Tofa] built after being there for two-and-a-half years.” 

While Taylor is bound to have some friends and family in the audience to show their support, it may be pretty hard to top the turnout he had over the summer during his initial four-week stint as Two-Bit. 

Taylor’s mother “set up a bus of 70 people from my hometown [in New Hampshire] and from Massachusetts, where I also have a lot of family, and she filled the bus with friends and family and teachers and mentors that I have,” he recalls. 

“They all took over the Sunday matinee. It was a really special moment,” Taylor explains. “Mom has come to the show, I think, 12 times. She’s my No. 1 supporter and fan. She’s always been there for me, and she’s seen every track at this point several times.” 

Being part of The Outsiders is “so special and so cool,” he adds. “I’m having so much fun up there with my friends, so I’m just lucky and excited to keep doing it.”