One Hit Wonder (2009)

Gil is at a crossroads in his life. After being fired from his job as a stockbroker, Gil decides that he must pursue his musical career one last time before giving up on his dream. Tom, his mailman friend, and a clueless cell mate of Tom's join Gil's quest for musical greatness. As they weave their way through the pitfalls of the music business, Tom's bookie is actively pursuing the collection of a debt.