Wet Hot American Summer wasn't played so straight, it wouldn't be nearly as good. It's a tricky line to distinguish sometimes, and it became nearly impossible to track in the 90s and early aughts. For every Wayne's World, you had a Night At The Roxbury. For every Office Space, a Me Myself and Irene.
In their attempts to find that next alt aesthetic to resonate with a mainstream audience, studios basically gave comedy writers a wide berth when it came to their projects. The results were really truly weird. As in "how the hell did anybody green light this" weird. Movies like Pootie Tang, Freddy Got Fingered, and Run Ronnie Run were all made under a variation of this model, and all probably rank up there with the strangest movies Hollywood has ever made. (Tellingly, Pootie Tang and Run Ronnie Run both suffered a lot from studio interference during their editing, showing that the studios got cold feet on this approach to comedy. All three bombed too, which is why you don't really see this stuff anymore.)
Walt Disney, under their Touchstone distribution wing, threw their own hats into the ring on this kind of comedy. The result was Cabin Boy, and it's...distinct. Originally a Tim Burton vehicle intended to be a tribute to Ray Harryhausen epics like Clash of the Titans & Jason and the Argonauts, the movie instead passed on to Adam Resnick and Chris Eliot once Burton left to direct Ed Wood. The Tim Burton connection is important because in a lot of ways the movie is similar to Mars Attacks!, another Burton movie. Both are clearly meant to be cult movies right out of the gate, and both tackle a genre long sedate by the time of their release. But while Mars Attacks! connection to sci-fi B movies is clear, Cabin Boy's is a bit more tangential.
We follow Chris Elliot's "fancy boy" character Nathaniel Mayweather, an upper class twit who has just graduated from Fancy Boy's Academy. Much like many of Adam Sandler's movies, a deciding factor in how much you can/will enjoy the movie is dependent on Elliot's voice, which manages to be a cross between a gay hairdresser and the snooty frat boys from Animal House. It's probably one of the more annoying aspects of the movie, and is unfortunatly so prominent throughout the film that it's hard to ignore. I get why it's there, but it's so distracting that it's kind of impossible to completely block out, which is a shame because the rest of the movie is surprisingly strong.
I don't want to give the wrong impression here. This movie is not some hidden overlooked work of genius that should be held up in the halls of comedy history as a supreme example of blah blah blah. It's not that at all, it's incredibly slight, both in length and content. Yet it's a very endearing movie in it's own way, partially just because it's so freaking strange. After Nathaniel graduates, he gets on the wrong boat and instead of heading to his father's lavish hotel in Hawaii he is stuck on a salty fisherman's boat heading right towards Hell's Bucket, a dangerous stretch of ocean few make out of alive. Along the way they meet a young woman who is trying to swim around the world (Melora Walters), a shark man named Chocki, a floating cupcake that chews tobacco, and more. Like I said, weird.
The weirdness definitely works in the movie's favor though. I hate to really use this as criteria for reviewing a movie, because saying you need to be in an altered state to really enjoy something isn't a great marker for quality and pretty cruddy criteria to rate something on, but fuck it, this movie was meant to be seen high. It's a stoner comedy without the weed. Though a parody of Harryhausen, it reminds me much more of the shows made by Sid and Marty Krofft. The high concept stranger in a strange land adventure accompanied by trippy visuals and it's irreverent tone all match up pretty well with the offerings of the brothers Krofft. Maybe that helps explain it's box office failure too, as movies with a basis in Kroftt works historically tend to not do so well.
I wouldn't say the movie works as a whole, if that makes sense. Like, if you were to look at this very analytically and dryly I don't think it would be a stretch to say there is a lot of rushed plot points. The movie basically introduces our character, drags it's feet to the premise, then shuffles through it while looking distractedly over it's shoulder at the shiny bits. When you're movie is only 80 minutes long and it feels padded that's generally not a good sign. It really feels like a comedy skit dragged on as long as it can go for to qualify as a movie.
On the other hand, when it's on it's really really funny. Alfred Molina makes an inspired appearance as a working giant/god who has to deal with a cheating wife. Andy Richter is pretty wonderful as well playing a dumb cabin boy. His interactions with Chris Elliot are among the strongest parts of the movie and one of the few times Elliot's voice really worked in the context of the scene instead of just being distracting. A heatstroke induced feverdream makes for another really funny sequence. It has little to nothing to do with the rest of the film, but it's a nice little detour. Chocki the sharkman starts off as funny, then stupid, then stupid funny, before finally coming around to hilariously funny.
But by far the best part of the movie happens very early on and lasts about two minutes. One of the little quirks associated with this movie is that it's one of the very few movies late night talk show host David Letterman has been in, and the only in which he wasn't playing himself. Well, sort of, as he's totally just being Letterman here, just not behind a desk. It's an absolutely brilliant cameo, a quick tour de force that manages to squeeze in about 5 endlessly quotable lines in rapid succession. Honestly, I've watched that scene about 7 times since I started writing this and it gets funnier every time.
Cabin Boy isn't a great film, and I don't even know if it's one deserving of remembrance. But despite it all it manages to be immensely charming in it's own weird way. If you have a bong on hand and this comes on the cable rotation, give it a shot. It's a fun little movie that manages not to overstay it's welcome. On the Wicker Scale, Christopher Lee is trying the London Broil.