New York City Serenade is a 2009 dramatic comedy directed by Frank Whaley. In the film, Owen (Freddie Prinze Jr.) and Ray (Chris Klein) are lifelong best friends who live in New York City. Owen is a struggling filmmaker who has a dead-end job and a gorgeous fiancee, Lynn (Jamie-Lynn Sigler), who he is not faithful to. Ray (Chris Klein) is a charming wanna-be drummer who plays in an amateur band and works at a dead-end job. When the duo are not working on their independent projects, they spend most of their time together drinking beer and getting into mischief. When Owen's short film is accepted by The World Wide Film Festival in Los Angeles, he thinks his life may finally be turning around. When things do not go as planned, Owen ends up taking Ray with him on his road trip to LA, and they have all kinds of unexpected encounters.