Swingers - 1996

Director: Doug Liman

Writer: Jon Favreau

Starring Jon Favreau, Vince Vaughn, Ron Livingston, Heather Graham

"Vegas, baby! Vegas!" Mike (Favreau) is a heartbroken, unemployed actor and recent transplant to Los Angeles. To ease his sorrows, Mike's friends (Vaughn & Livingston) take him to Vegas, then out exploring the LA nightlife.

Jon Favreau deserves a lot more credit than he gets in the industry. Between his writing and acting in this and his directing of the Iron Man franchise (not to mention the rest of his career), I'd say he's in the top 25% of filmmakers currently in the business. The environment is rich, the characters are relatable (even Vaughn, who I normally can't stand)...it's just plain entertaining and well-written. The icing on the cake: Mike and his friends (all playing characters based on themselves, as Favreau had a similar experience when he first came to Hollywood), with the element of the 1990s swing music revival included, are analogous to the original five-member Rat Pack. It's a highly underrated modern classic; see it now if you haven't yet.