Watch Who's the Caboose?

The independent comedy film "Who's the Caboose?" from 1997, written and directed by Sam Seder, follows the misadventures of actress Susan (Sarah Silverman) and her struggling comedian boyfriend Max (Sam Seder) as they navigate the cutthroat world of show business while attending a New York-to-Los Angeles "New Artistic Voices" showcase.

Max, who's desperate to make it big and attract agents, convinces Susan to come to Los Angeles to audition for the showcase. Together, the couple leaves behind their comfortable lives in New York and embarks on a journey that will test their relationship and their dreams.

Upon arriving in LA, they meet with their agent, Sam (H. Jon Benjamin), a perpetually smoking and blasé figure who offers little support or encouragement. They also encounter other aspiring actors, including Alex (Alex Ferrer), a loquacious and over-eager documentarian who becomes infatuated with Susan, and Amy (Laura Silverman), a fellow New Yorker who offers Susan a place to stay.

In their quest to make it big in Hollywood, Max and Susan face numerous obstacles, from a housing crisis that forces them to share a single room at a shady motel to the brutal competition of the showcase, where they learn that their New York-style humor doesn't play well with LA audiences.

As the showcase nears, Max becomes increasingly desperate and unhinged, going to great lengths to impress the judges, including staging a controversial and potentially career-ending stunt. Meanwhile, Susan begins to doubt her own abilities and whether she truly wants to make it in show business.

Throughout the film, Seder and Silverman deliver sharp, twisted dialogue that skewers the entertainment industry while also highlighting the struggles and insecurities of aspiring artists. Ferrer's performance as the gregarious but clueless Alex provides much of the film's humor, while Benjamin's deadpan delivery captures the indifference of agents and other industry insiders.

Despite the film's low budget and DIY aesthetic, "Who's the Caboose?" manages to capture the anxiety and absurdity of trying to make it in Hollywood, from the dehumanizing slog of auditions to the Hollywood parties filled with superficiality and empty promises. It's a darkly funny and biting satire that still resonates today, more than two decades after its release.

Who's the Caboose? is a 1997 comedy with a runtime of 1 hour and 34 minutes. It has received moderate reviews from critics and viewers, who have given it an IMDb score of 5.7.