Okay, first of all, there is a point I must make clear: I do not believe in guilty pleasures. The idea, that we should feel bad for enjoying a piece of pop culture, is a social construct that I completely disagree with. The very premise of a guilty pleasure is predicated upon the concept that other people will think poorly of us if they find out we enjoy something that was created for the sole purpose of people’s enjoyment. For example, I like the music of Justin Timberlake. There, I said it. I in no way feel bad about it. He created his music to be catchy – why would I feel bad for singing along?

Cabin Boy just can’t decide what time period it takes place in, and it actually adds to the humor. That being said, my first entry into this category is 1994‘s Cabin Boy starring Chris Elliot, James Gammon, and Brian Doyle Murray. It was written by Chris Elliott and his partner Adam Resnick, and directed by Resnick. It also boasts a rare cameo by late-night talk show host David Letterman, who appeared in the movie as a personal favor to his friend and late night cast member Elliott. Letterman’s credit at the end of the film lists him as Earl Hofert, an inside joke on a character he played in some skits early in his late night career.

The movie follows Elliott’s Nathaniel Mayweather, an overprivileged Fancy Lad, as he graduates from his school and travels to Hawaii to take up a position at a hotel owned by his father, played by Elliott’s real-life dad and comedy legend Bob Elliott. As young Nathaniel makes his way to the wharf from which he will depart, he takes the wrong turn at a fork in the road, and ends up aboard the Filthy Whore, a fishing ship filled with salty seamen, including Murray’s Skunk and Gammon’s Paps. What follows is a series of incidents caused by Nathaniel’s idiotic selfishness.

Upon its release, Cabin Boy failed to find an audience, and it was subsequently considered a flop. Its failure would ultimately damage the careers of Elliott and Resnick – Resnick wouldn’t get another screenplay to the theaters until 2000’s Lucky Numbers (and of course 2002’s Death to Smoochy, another favorite of mine). But since then, its stock has risen, and it’s become a cult classic. So what makes it so enjoyable?

First off, there’s Elliott himself, whose stock and trade is playing an idiotic man-child who thinks he’s better than everyone else. His buffoonery carries the movie, as his idiocy both gets him into and haplessly out of sticky situations. Take his entrance onto the Filthy Whore – he assumes he is on the right ship, despite all evidence that he is not. He instead thinks it’s a theme ship, only meant to look like it’s a dirty wreck, and begins ordering around the steward Kenny, played by Andy Richter. His stupidity even gets him out of trouble, like when he’s on the island in Hell’s Bucket, and he’s forced to answer riddles given to him by the green, multi-armed Calli. He can’t manage to figure out anything, prompting Calli to utter the line, “Come on over here, honey. You’ve managed to charm me with your moronic innocence.”

There’s also all the bizarre incidents that occur throughout the movie. When discovered by the crew of the Filthy Whore, Nathaniel is placed on a raft tied to the back of the ship (stern, right?) and left to dangle for a week, in hopes that he would die. Eventually, Nathaniel consumes the only provisions he was provided (including a jug of chocolate milk), begins to hallucinate, and falls into the water. He is saved by the legendary half-man-half-shark Chocki, much to the amazement of the crew when they reel him in after nine days (they forgot he was out there).

Finally, the film is filled with beautiful anachronisms. Cabin Boy just can’t decide what time period it takes place in, and it actually adds to the humor. It seems to take place in the past, since Nathaniel wears a powdered wig and is stuck on an old fishing vessel, but then there’s the moment when he’s being driven partway to the wharf in a stretch limousine. Or when Nathaniel has become the ship’s cabin boy, and for dinner has prepared the crew a feast of frozen fish sticks, cooked in the ship’s microwave oven.

Whenever I tell people about my love for the film, I get one of two reactions: either a) they’ve never even considered seeing it, or b) disbelief that someone would enjoy that piece of garbage. Either way, I’m still happy to be one of its guiltless loyal fans. I, therefore, leave it to you to decide for yourselves. However you decide, please rest assured that you should not feel guilty about it.