New York City Serenade (2007)

The comedic drama New York City Serenade (2007) stars Freddie Prinze Jr. as Owen, a struggling filmmaker who has just been dumped by his fiancée (Jamie-Lynn Sigler), which leaves him with an extra plane ticket to a film festival in Kansas. He decides to ask his old friend Ray (Chris Klein), a drunken aspiring rock star, to go with him. Once they arrive, Ray makes trouble by impersonating Wallace Shawn’s son to get a better room at the hotel, and Owen tries to patch things up with his fiancée. There’s no nudity here, but we do get to see Heather Bucha in her underwear as she argues with Chris Klein.