Like everyone starting out in musical theater, Jeremy Jordan had a song from "The Last Five Years" ready to go in his back pocket.
Jordan, the Tony Award-nominated star of "Newsies: The Musical" and TV's "Smash," had fallen in love with the Jason Robert Brown musical when it premiered in 2002 and added one of its tunes to his audition list.
"It was like the bar. It was the apex. It was like the thing you strived for," he recalled. "If you could do justice to a song from 'The Last Five Years,' then you were in good shape as a musical theater actor."
Now Jordan has upped his game: He's gone from having one of its songs down pat to starring in the first-ever movie of Brown's cultishly adored song cycle about a young couple's falling in and out of love.
"It was fun because I knew it so well and I felt like I really connected to it when I first heard it and I still connected to it," Jordan said. "I got to share that love and connection with everybody else."
Jordan co-stars alongside Anna Kendrick in the 95-minute film, which has been adapted and directed by Richard LaGravenese and hits theaters and video on demand Friday after making its premiere at the Toronto International Film Festival.
It's the five-year love affair – told almost entirely in song – of aspiring actress Cathy and budding novelist Jamie, one on the rise and the other finding the going frustrating in mid-1990s New York.
Brown structured the story with a twist: Jamie starts at the beginning of the relationship and alternates songs with Cathy as he moves to the crushing end, while Cathy begins at the end and moves in reverse chronological order to the couple's sunny origin.
While Brown had been approached about turning the musical into a film for years, no proposal really excited him until he spoke with LaGravenese, the writer and director of "Beautiful Creatures" and "P.S. I Love You."
"I always thought it might make a nice movie, but I never really had a sense of what that movie was supposed to look like or anything like that," said Brown, who has a cameo as an audition pianist. "I'm very proud of it."
LaGravenese added some quirky, surreal touches and dance numbers to the heartbreaking naturalism of Brown's songs, and he made it modern with the use of Skype and cellphones. LaGravenese also pulled the theatrical piece into the world of film by having the young lovers in the same scene, even if only one was singing.
It was filmed over 2 and a half weeks in New York during the sweltering summer of 2013 and maintained its intimacy by having 90 percent of it sung live. Prerecording the songs and then lip-synching them for cameras weeks later wasn't an option.
"You write songs about moments that are special, that are particular, that are meaningful and that are impactful. Every moment in the film is one of those moments," said Jordan, who, during the song "Moving Too Fast," actually bikes through the city while singing. (The soundtrack is available for download.)
Things got a little more real than the crew bargained for during a lunch break on the last week of filming when a thief opened the unlocked costume truck and made off with most of Jordan's clothes, including four pairs of expensive jeans cut specifically for Jordan.
"I was like, 'What are you going to do with a bunch of dude's clothes that are sized specifically to Jeremy Jordan's butt?'" he said, laughing. "I guess you have to find some very specific clients for that."
The finished film is something that Brown admits is still startling, even though the musical is done hundreds of times across the globe every year. His small, semi-autobiographical story is now on a huge screen, being sung by stars with enormous faces.
"That part was an incredible head trip," Brown said, laughing. "I don't think there's any way for me to have prepared myself for that. When did everyone get so big?"