If you want to make a movie, you can. That’s not to say it won’t take a lot of work from a lot of friends, and potentially, even more money, but it can be done. Twenty years ago, not so much. That’s what makes the 1997 film Who’s the Caboose? incredible. Co-written and directed by Sam Seder (Majority Report, Bob’s Burgers) and starring himself and Sarah Silverman, the film tells the tale of a young indie New York standup who makes her way to Los Angeles to break into television, and the effect it has on her relationship. It features young versions of Jon Benjamin, David Cross, Andy Dick, Andy Kindler, Marc Maron, Todd Barry; basically the entire early indie comedy scene of the day. Who’s the Caboose? launched some folks, according to the oral history of The State book it inspired Wet Hot American Summer, it perfectly skewered the Los Angeles system, and yeah, it’s a little dated. Jon Benjamin uses a car phone at one point. But most importantly it’s funny, and it’s not the focus of this article.
This article is looking at the sequel to Who’s the Caboose?, a six-episode TV series entitled Pilot Season that aired on the now defunct channel Trio. Now, I could write a 200 page treatise eulogizing this Letterman rerun broadcasting, Lookwell airing network, but let’s just focus on Pilot Season for today, okay? (That sass was directed towards myself, not you.)
Pilot Season picked up seven years after the film left off exploring what happened to these characters after Los Angeles happened to them. Where Who’s the Caboose? explored what the TV system was like for hungry newcomers trying to make their way through a narrow pipeline of TV networks, Pilot Season examines what it’s like to be the part of the machine that isn’t quite working as efficiently as the rest of the cogs.
Pilot Season assumes that you never saw the movie it’s based on, which is probably a good idea since not a lot of people have seen it. We learn that within the world of the movie, Who’s the Caboose? was never released because Susan, Silverman’s character, refused to sign the release form. She and Max, Seder’s character, broke up in the movie, and he became her agent. Since then, she has moved on to a larger agency where she is repped by Marc Victor, as portrayed by Marc Maron. Susan is clearly doing well, living in a huge California mansion which she tours with the camera crew. As they walk towards the patio, she begs them not to shoot her kitchen because it’s such a mess (It’s huge, and the only mess is a bowl of fruit neatly placed on the counter). She informs the production of Pilot Season that her manager has recommended that she should only do one interview. Obviously, since Max has refused to let Susan out of his life after all this time, that’s not going to be the case.
After Susan left Max for the larger management company, she also provided him with a golden parachute: Big Management had to bring Max on as a manager at their company. Things are not going so well for him. In fact, in a one-on-one interview with his boss, we’re told that Max is going to be fired in eight weeks. This would make sense, since in the first episode of this we see him stalk Susan into a fancy home goods store where he’s forced to drop $4000+ on a pair of blankets to save face, harass his assistant (Chris Fairbanks), and embarrass himself in front of an old friend who dropped out of the acting game, played by Matt Besser. Oh, and he attempts to meet up with another old acting friend, played by David Cross, who is hanging out in his trailer on the set of a crime drama. However, once a producer shows up and yells at David for being in there, it becomes pretty clear that his uniform is that of a security guard, not a TV policeman. This encompasses three days of work for Max, with nary a client managed.
While the mockumentary had been a form exploited for comedy by Christopher Guest and countless others in film for years, in 2004 when Pilot Season emerged, in America there was Arrested Development and that’s it. The Office had already aired in England, but was still a year away from launching in America and with it, ushering in a million more mockumentaries on the US airwaves.
Sadly, just a few weeks after Pilot Season premiered as Trio’s first original series, DirectTV announced that it would no longer be carrying the channel, effectively taking away two thirds of its audience and killing the network. The six episodes of Pilot Season would be all she wrote for the on again, off again, still off adventures of Susan and Max.