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Before I give you my list, I want to make it clear that I don't use a term like "guilty pleasure" lightly.

Clarification #1: I don't feel embarrassed to admit I'd rather watch Patrick Swayze' Roadhouse over Ang Lee' Brokeback Mountain. It doesn't humiliate me to disclose I'd watch Evil Dead II over Hotel Rwanda any day of the week. Liking dumbass movies isn't anything to feel guilty about, damn it. I'm zen enough with my taste in films (or lack thereof) to come clean that I get more pleasure out of the Die Hard trilogy than Schindler' List.

Clarification #2: When I throw around a term like "guilty pleasure comedy," I don't mean watching it on TBS if there' nothing else on. I mean that you went out to a Best Buy and put money down on a counter in front of other human beings and bought the fucking thing. These are movies you need to hide behind the toilet when you have friends over. If you have a girlfriend or wife, these are movies which you've made a pact with her on: should anyone ask, these are her movies. Her movies that you hate.

With that out of the way: my list of the most embarrassing comedies to get caught owning, that are actually really good.


8
Cabin Boy
GUILT ALERT LEVEL: BLUE

WHY IT'S A GUILTY PLEASURE
Regardless of Cabin Boy' content, its ridiculous nautical premise and unfathomable marquee billing of Chris Elliott make it just sort of... look dumb. It' the film equivalent of the comfortable pants you wouldn't be caught dead wearing to a party.

WHY IT'S SECRETLY AWESOME
Because it' funny. Chris Elliott subverts his leading man role into the wussiest mewling sissy you've ever seen. You're not rooting for his character to win so much as enjoying him getting nailed in the crotch with an anchor for the eleventh time. (I don't remember if this actually happens, though you have to admit, it sounds plausible.) It' good damn fun.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
Minimal. Owning a DVD with as questionable value as Cabin Boy is a mainstay of anyone' collection. Even that snooty cinephile you try to avoid who' always namedropping Ingmar Bergman probably has a copy of Hot Shots: Part Deux tucked away at the back of his DVD shelf. We're all allowed a few stinkers. With the lone exception of G.I. Jane, which you shouldn't own, ever, for any reason.


7
Multiplicity
GUILT ALERT LEVEL: GREEN

WHY IT'S A GUILTY PLEASURE
Technically, it' a romantic comedy. Plus it stars charisma vacuum Michael Keaton and almost-entirely-composed-of-teeth-and-gums Andie MacDowell, despite the fact that filmmakers should know better by now. Most insidiously, the film' message is that spending more time doing what your wife wants is, in the end, more important than your own hopes and dreams.

WHY IT'S SECRETLY AWESOME
It' written and directed by Harold Ramis, the guy who wrote Ghostbusters and Groundhog Day, which alone should cut the movie some slack. Also, much like Ghostbusters and Groundhog Day, Multiplicity' got a cool high concept premise to bounce the laughs off of. And as a mitigating factor to it starring Michael Keaton, note that it also stars Michael Keaton acting like he' retarded. Not for an Oscar nom, either. For laughs.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
You'll live. It' not an offensively bad film-if people've put any thought into Multiplicity at all, the worst prejudice against it is that it' bland and forgettable. It's the sort of film you'd rent if you had your parents visiting and didn't want anything to offend. You could probably get away with "My grandmother bought it for me as a gift" if pressed.


6
Last Action Hero
GUILT ALERT LEVEL: GREEN

WHY IT'S A GUILTY PLEASURE
If you haven't seen it, SPOILER ALERT: it' not very good.

WHY IT'S SECRETLY AWESOME
The opening minute of Last Action Hero casts Arnold Schwarzenegger as Hamlet. Arnold Schwarzenegger. As Hamlet. It is one of the ten most awesome things you will see in your entire life. The rest of the movie I could care less about. Sadly, YouTube only had the Spanish version available. I apologize in advance:



DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
This depends on how many other, superior Schwarzenegger movies you own. If you've got Last Action Hero sandwiched in between sweet films like Terminator 2 and Predator on your DVD shelf, don't sweat it. If you've got Last Action Hero sandwiched in between The Last Boy Scout and Hudson Hawk on your DVD shelf, you're clearly some kind of fucking idiot. Your friends won't say anything — but they will never take your movie opinions seriously again.


5
Stuart Saves His Family
GUILT ALERT LEVEL: GREEN

WHY IT'S A GUILTY PLEASURE
Good God, where to start? It' a mid-90' SNL movie, so Strike One. It' a mid-90' SNL movie based around one of SNL' least popular characters ever. Strike Two. Plus it' a comedy about a family baring their souls and weeping openly while in therapy. Swwwwwing and a miss.

WHY IT'S SECRETLY AWESOME
Stuart Saves His Family is really dark, with lots of cruel humor at the expense of its protagonists. Harold Ramis, the film's director (see Multiplicity) and writer Al Franken aren't under the illusion that anybody likes the annoying Stuart Smalley. The film is essentially one big funny joke at his expense.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
Medium to high. This is a good comedy that' got chips stacked against it for all the reasons just mentioned. It looks like it should suck, it sounds like it should suck; therefore, in the court of public opinion, it blows. Trying to convince a friend that it doesn't would be like trying to convince a friend it wouldn't be weird if you gave him an enema.


CLICK TO THE NEXT PAGE FOR
THE FOUR GUILTIEST MOVIES OF ALL TIME
4
Mickey Blue Eyes
GUILT ALERT LEVEL: YELLOW

WHY IT'S A GUILTY PLEASURE
In his blog Dave' Long Box, David Campbell explains something called The Richard Gere Factor. I'll let him explain it:
"The Richard Gere Factor is a form of typecasting and brand identity that prevents men from identifying/liking a male performer or character. It all started with American Gigolo and kept rolling from there. After decades of roles as the love interest in — forgive me — chick flicks, Gere is now more of a lady' man than a man' man. The male viewer subconsciously perceives Gere as a rival, as a threat, and as a result, we hate him for it."
Hugh Grant is the comedic version of Richard Gere. Males are genetically programmed to despise him.

WHY IT'S SECRETLY AWESOME
Let' put aside for a moment that I think Hugh Grant is one of the most underrated comedians of all time (watch About a Boy and tell me he doesn't own that movie). Even assuming you utterly despise Grant' bumbling persona, Mickey Blue Eyes rocks because it' parodying that persona. Take Grant' awkward, foppish twat character. Then make Jimmy "Sonny Corleone" Caan attempt to turn him into a mobster killing machine. I hate to split hairs about what' funny and not funny, but — well, I'll say it again: James Caan tries to make Hugh Grant into a badass. That' funny by definition.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
High: the Richard Gere Factor cannot be ignored. Hugh Grant stars in tweedy romantic comedies you don't like. This movie stars Hugh Grant. Ergo, Mickey Blue Eyes is a tweedy romantic comedy you won't like. It' hard to argue with airtight logic like this, even when it' completely wrong.


3
DeathStalker II
GUILT ALERT LEVEL: YELLOW

WHY IT'S A GUILTY PLEASURE
Because it sorta looks like — and, well, sorta is — a no-budget direct-to-video softcore porno with swords and wizards in it. There' really no tactful way you can go out and buy a copy of this at Blockbuster without the cashier immediately assuming you're about forty minutes away from enjoying it on a wholly unsavory level. Deathstalker II is the movie eBay was invented to purchase.

WHY IT'S SECRETLY AWESOME
Because everyone involved in the production of Deathstalker II is hyper-aware of how enormously ridiculous Deathstalker II is. They all clearly had a load of fun making this piece of shit, and there are scenes so incredibly self-conscious of their own awfulness, they achieve some kind of reverse-coolness as a result. Case in point: at one point Jarek the Evil Sorcerer (John Lazar) plots the death of our hero Deathstalker with a nearby villainess, chewing vast amounts of scenery while doing so. One should also mention that John Lazar has decided to play Jarek the Evil Sorcerer as the Gayest Man Alive:

Seriously, there's "coming off a little gay," and then there's Jarek the Sorcerer, who gives you the impression that whenever he's not in a scene, he's somewhere off camera with at least five distinct cocks in his mouth. At any rate, Jarek lisps, "Oh, I'll have my revenge…", then looks directly at the camera and swishes, "…and Deathstalker TWO! MOO HOO HA HA HA!" Then the title card Deathstalker II splashes across the screen. If that makes you smile (and I can't conceive why it shouldn't), you will enjoy this movie.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
Not a big deal if friends catch you with it, but crippling if your date notices it while scanning your DVD collection. Owning Deathstalker II is like admitting you enjoy Dungeons & Dragons so much you went out and bought a version of it you could yank off to.


2
When Harry Met Sally...
GUILT ALERT LEVEL: ORANGE

WHY IT'S A GUILTY PLEASURE
It's the Nora Ephrom romantic comedy from which all other romantic comedies were spawned. Movies like Sleepless in Seattle and You've Got Mail would not exist if it hadn't been for When Harry Met Sally. For accumulative aftershock alone, When Harry Met Sally is the event horizon of awful romantic comedies: it is the boundary at which the escape velocity for a given male reaches and then exceeds the speed of light, making escape impossible.

WHY IT'S SECRETLY AWESOME
Discounting the hundreds of shitty RomComs floating in its wake, it is admittedly the Gold Standard of the genre. You know how any mobster flick will inevitably be held up to The Godfather, or how a space western will have to weather comparisons to Star Wars? Every romantic comedy from 1989 onward is judged on its merit in relation to When Harry Met Sally. How bad could it honestly be? It' the Citizen Kane of relationship movies.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
Assuming you can't pretend it' your girlfriend' copy? Unimaginable. Owning pretty much anything with Billy Crystal in it is cause for alarm â€" that the movie also contains dangerously high quantities of Meg Ryan is reason enough to wash your hands thoroughly after coming into contact with the DVD case.


1
Pretty Woman
GUILT ALERT LEVEL: RED

WHY IT'S A GUILTY PLEASURE
This couldn't be more of a chick flick if they'd called it No Boys Allowed and distributed free tampons with every DVD purchase. Pretty Woman is the ultimate girl fantasy: handsome billionaire Richard Gere (!) spends the film taking Julia Roberts shopping, listening to her problems and learning to love the person inside before proposing his undying love to her.

WHY IT'S SECRETLY AWESOME
There' a reason America fell in love with Julia Roberts after Pretty Woman came out: Julia Roberts is infinitely loveable in this movie. I don't care how much of a raw meat-eating He-Man you see when you look in the mirror — you can't watch Pretty Woman and not root for her all the way.

DEGREE OF EMBARRASSMENT IF CAUGHT WITH IT
Getting caught by a friend owning a copy of Pretty Woman, by even the laxest standards of manliness, means you physically do not have balls. It will be incorporated into every drunken punchline at your expense for the next decade. Do what I do: wait for your girlfriend to rent or buy it, roll your eyes in pretend agony, and then go microwave some popcorn.
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