Waiting (2005)

A waiter for four years since high school, Dean (Justin Long) has never questioned his job at Shenanigan's. But when he learns that Chett, a high school classmate, now has a lucrative career in electrical engineering, he's thrown into turmoil about his dead-end life. Dean's friend Monty (Ryan Renolds) is in exactly the same boat, but he couldn't care less. Monty is put in charge of training Mitch (John Francis Daley), a shy new employee. Over the course of one chaotic shift, Mitch gets to know the rest of Shenanigan's quirky staff: Monty's tough-talking ex-girlfriend, Serena (Anna Faris), Shenanigan's over-zealous manager, Dan (David Koechner), and head cook Raddimus (Luis Guzman), who's obsessed with a senseless staff-wide competition known only as "The Game".

Official website: http://waitingthefilm.com/