When the film was being planned by Paramount, executives thought that Kevin Spacey was too old to portray Bobby Darin, who died at 37, and wanted Leonardo DiCaprio instead.
When financing looked as if it might fall through just before filming was to start, Kevin Spacey persuaded Lionsgate Vice Chairman Michael Burns to get that studio on board by driving Burns around in a car and playing a medley of Bobby Darin songs. At some point Burns made an observation about Darin's singing. Then Spacey told him, "That's not Bobby Darin, that's me."