[3][citation needed] He is a graduate of St. John's Military Academy (Delafield, Wisconsin) and Clarke College (Dubuque, Iowa).
[4] After college he moved to New York City's East Village, where he landed a day job in book publishing and wrote fiction and plays at night.
[6] His play Red Light Winter received the Joseph Jefferson Award (Best New Work) in 2005 for its production at Steppenwolf Theatre Company.
Rapp wrote on the book for The Outsiders: A New Musical, a re-imagination of the 1967 S. E. Hinton novel and the 1983 Francis Ford Coppola film adaptation.
He combines humor with gloom, preferring dark themes[14] In a conversation with fellow playwright Gina Gionfriddo published in The Brooklyn Rail, Rapp says: "When you see something powerfully acted on stage, it hits a nerve in the way music hits a nerve … Watching someone twelve feet from you falling in love or being abused … There’s something raw about that experience that you don’t get from film or TV.
After writing his second book, The Buffalo Tree, which was published in 1997, Rapp was invited to be the first author in residence at Ridgewood High School.
[17] The Buffalo Tree was censored by the Muhlenberg School Board in Reading, Pennsylvania due to its themes, graphic language and sexual content.
Rapp directed his first film, Winter Passing, with Zooey Deschanel and Will Ferrell in 2005[23] and was a creative consultant for the television show The L Word.
[24] While working on The L Word, Rapp left in the middle of the season to attend the Edinburgh Festival, where he directed his play, Finer Noble Gases, which won the Fringe First Award.