70. Swingers (1996)
Directed by: Doug Liman
Starring: Jon Favreau, Vince Vaughn, Ron Livingston, Heather Graham
Synopsis: Out of work actor in Los Angeles, obsessed with his ex-girlfriend, is pushed by his friends to start dating again.
You’re so money and you don’t even know it- Vince Vaughn as Trent
Independent films had their heyday in the 90s with this movie and a few other gems upcoming on this list. Favreau, who also wrote the film, was chiefly known as the buddy in a flick about college football (also coming later.) Vince Vaughn, as Trent, became a star. I also have this movie to thank for introducing me to Big Bad Voodoo Daddy.