Jason Robert Brown's Drama Desk winner, The Last Five Years was written during the two years that Jason Robert Brown toured the country as conductor and musical director of the national tour of another one of his shows, Parade. Distraught with the state of musical theatre style at the time, he wanted to create an emotionally intimate, musically complex piece. Brown's musical style, although it only uses a select number of instruments, draws on a significant number of genres, from classical to rock to klezmer.
The Last Five Years premiered at the Northlight Theatre in Skokie, Illinois and was named one of TIME Magazine's ten best shows of 2001. The production ran for two months and starred Lauren Kennedy and Norbert Leo Butz. The show reportedly sold more tickets in a single weekend than any other production at that theatre before.
With new producers, the musical later opened at the Minetta Lane Theatre Off-Broadway on March 3, 2002, closing on May 5 of the same year. Sherie Rene Scott stepped in to star opposite Butz, as Kennedy had taken off for a prior commitment. Since its closing, The Last Five Years has been produced across hundreds of American cities, in addition to Australia, Germany, Netherlands, Italy, France and the Philippines. The musical's regional popularity spurned an Off-Broadway revival at the Second Stage Theatre in 2013. It was directed by Jason Robert Brown, himself. A film adaptation was released in 2014, starring Anna Kendrick and Jeremy Jordan.