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‘What if’ questions pay off for Tony-winning duo behind ‘If/Then’

Composer Tom Kitt (far left) and playwright/lyricist Brian Yorkey, the creative team behind “If/Then.”
Composer Tom Kitt (far left) and playwright/lyricist Brian Yorkey, the creative team behind “If/Then.” (Jennifer Taylor for The Boston Globe)

NEW YORK — Over the years, composer Tom Kitt always marveled at the “what if” questions of his life. There were the roads not taken, but also the seemingly random events and choices that helped make his life turn out the way it did.

After college, for example, he chose the arduous path of becoming a musical theater composer, instead of parlaying his economics degree into an investment banking job on Wall Street.

Most significantly, Kitt points to his freshman year at Columbia University when a knock on his door changed his life forever. Materializing in his dorm room was a resident adviser and aspiring actress, Rita Pietropinto, who was desperately searching for someone to play the music for the school’s annual “Varsity Show,” a celebrated campus tradition of satirical sketches and songs that counts Richard Rodgers and Oscar Hammerstein among its alumni. She had heard he played piano and had perfect pitch, so he could pick up the music quickly. She handed him a tape of the songs, and Kitt agreed to step in at the last minute. The following year, she convinced Kitt and her friend Brian Yorkey to team up to write all the music for the 100th edition of “The Varsity Show.” Pietropinto would eventually become Kitt’s wife, and Yorkey wound up as his longtime musical theater collaborator. The duo went on to win a Pulitzer Prize for drama and a Tony Award for best score, for their 2010 musical “Next to Normal.”

Kitt’s fascination with the different paths our lives can take eventually became the backbone for his and Yorkey’s musical “If/Then,” which follows two possible versions of one woman’s life. The show premiered on Broadway in 2014 starring Idina Menzel. A touring version comes to the Boston Opera House, Tuesday through July 17, starring Jackie Burns, Anthony Rapp (“Rent”), and Tamyra Gray (“American Idol”).

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While “If/Then” received mixed reviews in its debut, it had its champions, with New York magazine critic Jesse Green calling it “one of the most compelling new musicals in years.” It ran for more than a year on Broadway, and its cast recording became the highest-charting debut for a Broadway cast album since “Rent” in 1996 (“Hamilton” has since smashed the record).

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In writing “If/Then,” the writers wanted to explore “the idea that the important things that change your life are meant to happen,” Kitt said. “I want to feel like I was meant to meet Brian. I was meant to be a composer. I was meant to meet my wife and have our three children. There were a number of factors that led to all of that happening, which if you mapped it out, you would say, ‘God, a lot had to go right for all of those things to line up.’”

The story that he and Yorkey dreamed up centers around the character of Elizabeth (played by Burns), an urban planning expert on the cusp of turning 40 who returns to New York from Arizona to restart her life after a divorce. She’s slightly neurotic and tends to overthink and obsess over her decisions.

With a nod to the 1998 Gwyneth Paltrow film “Sliding Doors,” the show splits Elizabeth’s life in two directions, which pivot on one seemingly meaningless choice she makes early on — whether to stay in the park with her new friend Kate (played by Gray) or join her friend Lucas (Rapp), an old college friend and community activist, at a protest event. In one of the show’s two parallel tracks, Elizabeth becomes the bespectacled Liz, who falls in love with an Army doctor and starts a family, with her professional ambitions taking more of a backseat. Meanwhile, the other path follows “Beth,” who gets a high-profile job in the city planning department and focuses on career advancement. Yet she finds her romantic life wanting, embarking on an affair with her married boss.

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“The show does that thing that we often wish we could do, which is say, well, what if I’d done that instead of this? What would my life be?” Yorkey says. “There’s a lot of difference between those two paths, but also we find there’s a lot that they have in common. In both lives she experiences joy and heartbreak in different ways, but sort of in equal measure.”

Kitt and Yorkey were seated across from each other inside the office of “If/Then” producer David Stone (”Wicked”) last spring following rehearsals for a workshop production of “Freaky Friday,” a new musical they’re adapting from the classic 1972 children’s novel and subsequent films. It will be staged in Washington, D.C., next fall. (They’re also writing musical adaptations of “Magic Mike” and the 2007 Tom McCarthy indie film “The Visitor.”)

In person, the duo are a study in contrasts. While Yorkey is voluble and gregarious, Kitt gives off a more measured vibe and looks like the preppy guy next door.

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In writing the pop-rock score for “If/Then,” Kitt says he wanted to create something that was emotionally melodic and captured the searching quality inside Elizabeth.

“It grooves in a way that a lot of theater music doesn’t necessarily groove. It’s very hooky,” attests Rapp over the phone. “And Brian’s lyrics are always very accessible and truthful and honest. The poetry is in the simplicity. He’s not writing tons of imagery. He’s writing in very direct ways that people speak, but finding a way to make that a lyric.”

Originally, Kitt and Yorkey conceived “If/Then” to be about a female character in her 20s. But Stone suggested shifting the character’s age to her late 30s.

“Well, it just seems to me that if you’re a little bit older, maybe you’re pushing 40, the stakes are higher because there’s a lot more time gone by,” Yorkey recalls Stone saying. “When you’re 23, you got your whole life ahead of you. You can [mess] up and make mistakes for a decade and still have plenty of time.”

Kitt and Yorkey agreed that making Elizabeth older “could be really compelling.” “Then David says, “Well, Idina Menzel is looking for a new show,” says Yorkey, imitating the producer’s deadpan delivery. “We were like, ‘You could have just led with that!’ ”

As for their more than 20-year collaboration, Yorkey points out that their teaming up on the 100th edition of “The Varsity Show” at Columbia only came about because Yorkey’s roommate and previous songwriting collaborator, Eric Garcetti, now the mayor of Los Angeles, was studying abroad that semester in Africa.

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“I joke around that Eric’s ‘If/Then’ moment is that he’s here with Brian writing musicals, and I’m the mayor of some city,” says Kitt, with a laugh. “No, you’re probably a billionaire on Wall Street!” cracks Yorkey.

Kitt says he believes “living involves making bold choices. You can’t always know how they’re going to turn out, and you can always play that game of wondering what might have been if you had made another decision.”

Indeed, Yorkey adds, “especially as you get older and you have more and more paths and choices behind you, it’s so important to not obsess over those choices but instead say, ‘Well, what’s the path ahead of me? What choices am I going to make now?’ ”

If/Then

Presented by Broadway in Boston at Boston Opera House, July 5-17. Tickets: starting at $44. 800-982-2787; www. BroadwayInBoston.com


Christopher Wallenberg can be reached at chriswallenberg@gmail.com.