Swingers (1996)

Swingers is a 1996 comedy-drama film about the lives of single, unemployed actors living on the 'eastside' of Hollywood, California during the 1990s swing revival. Written by Jon Favreau and directed by Doug Liman, the movie starred Favreau and Vince Vaughn, and also featured performances by Ron Livingston and Heather Graham. This film was rated #57 on Bravo's "100 Funniest Movies." The film was honored on the 2007 Spike TV Guys' Choice Awards.

Mike (Jon Favreau), a recent transplant to Los Angeles, has broken up with his long-time girlfriend of six years and is still having trouble letting go and moving on. His friend Trent (Vince Vaughn) takes him on an overnight trip to Las Vegas in an attempt to get him back in the game. Trent picks up a cocktail waitress (Deena Martin) and her actress friend (Katherine Kendall), but Mike's obsession with his ex-girlfriend spoils the one-night stand. Back in Los Angeles, Mike attends various Hollywood and Los Feliz hot spots, including The Derby, The Dresden Room and the Hollywood Hills Coffee Shop, while his friends, Rob (Ron Livingston), Charles (Alex Desert) and Sue (Patrick Van Horn) coach him on the rules of seduction. Mike makes several awkward attempts at speaking to women, but they all end disastrously. Along the way, the group discusses movies, video games, and their floundering careers in show business. When Mike learns to accept himself and eschew the pretenses and self-promotion involved in the Hollywood dating scene, he finally connects with a beautiful girl named Lorraine (Heather Graham). The next day, he gets a call from the ex-girlfriend he's been obsessed with but rejects her offer to get back together when Lorraine rings in on the other line. While discussing Mike's new situation at a diner, Trent interrupts to make a disastrous attempt at flirting with a woman nearby. As Trent tries to recover from the embarrassment, Mike smiles as the tables turn.