In this mock documentary, a filmmaker who has received a grant to make a feature about fatally ill homeless people decides at the last minute to instead turn his camera on Susan (Sarah Silverman), a stand-up comic who has decided to make the big move from New York to Los Angeles in hopes of breaking into television. However, she waits until the last minute to tell her boyfriend Max (Sam Seder) about this little change in her life. Max is surprised, but decides to tag along in an attempt to be supportive, even though once they get to California he finds they won't be living together as he expected. Susan dives into the Hollywood audition circuit head first, while Max stays with his friend Earl (David Waterman), who has a deal for a TV pilot, and gripes cynically about how superficial Hollywood can be. But while Susan finds she can't get a part to save her life, Max is suddenly the toast of the Hollywood hipster set, and suddenly everyone in town wants to offer him a deal for a pilot. Who's The Caboose? features a number of noted stand-up comics and TV personalities in supporting roles, including Andy Dick, Kathy Griffin and David Waterman; the film was screened as part of the 1999 San Francisco Jewish Film Festival.