Call it Halloween, call it the day after Devil’s Night (if you’re a fan of The Crow), call it the day before All Saints Day (that’s for all you Catholics out there), or just call it a pain in the ass. Like it or not, it’s time to dress up. Whether fun or a chore, it’s more important than it seems, and wearing the wrong costume can be disastrous. The right costume, however, will not only get you through the night unscathed, but it could also do wonders for upping your rep. Most important, not wearing a costume is not really an option. You’ll be viewed as Halloween’s equivalent to Scrooge. Going to a Halloween party sans costume is like not dancing to a band that moves you. Don’t be a dick. Wear a costume. Dance.
Be obscure, but not too obscure
You want to treat your costume as you would your favorite music: people shouldn’t be able to recognize it straightaway but it should only take you a few words to put the I-should’ve-known shame on their faces. Too obscure and you run the risk of sounding more pretentious than you want to be or, worse, uncool, as if you were talking about an unknown band that’s unknown because they’re terrible.
You and a friend dress as Drum and Mt. Heart Attack, and when people ask what you are all you say is “Drum and Mt. Heart Attack.” If they get it, cool. If not, you win. If they guess before you tell them, well, them’s the breaks, kid. (This costume requires a friend, which doesn’t give you much time to make one. If you’re partying solo, just wear a Pavement T-shirt and say you’re the guy from Weezer.)
Don’t dress up as a bushman and say that you’re actually the frontman for an aboriginal band that doesn’t record anything because they’re too poor. Don’t mention that they’re afraid of cameras. Don’t tell anyone that they don’t like whites in general but they like you for some reason because they can tell you’re pure. Don’t say that you’ve seen them like 50 times and that your cousin used to roadie for the bushmen and you could probably hang out with them any time you want.
Be edgy, not offensive
People love edgy humor, but are offended by offensive things. Learn the difference and you’ll party with your cred intact.
A sexual-position pun can be a good time for everyone. Be a donkey with a punch bowl or a neglected trombone that has succumbed to oxidation. There’s a fine line, however. Dressing up as a really angry guy in a Cleveland University sweatshirt riding a locomotive could offend certain Ohians. Similarly, dressing up as a teabag may be unintentionally offensive to Libertarians, so that’s a don’t.
Rob Schneider and all of his fictitious incarnations are strictly off limits. We, as a nation, have almost forgotten him. With Schneider, it will always be too soon. (Deuce Bigalow is the possible exception and certainty, in this case, can only be obtained the old-fashioned way. If you’re a risk taker, try it out.) Note that the same goes for Chris Kattan. (Under no circumstances say that you’re Chris Kattan dressed up as Deuce Bigelow.)
Be topical, but avoid pop-culture faux pas
It’s OK to keep abreast of the issues. In fact, it’s admirable. But make sure you’re on top of the right things. You don’t want to get caught mounting anything embarrassing.
No Jon & Kate (unless you have eight friends who are willing to wear adult diapers). No Michael Jackson—neither zombie MJ from the “Thriller” video nor corpse MJ from real life. No Chaz Bono. No McKenzie Philips and her dead dad. No Octomom. No boy in the aluminum balloon. No Chesley Burnett “Sully” Sullenberger III. Ironic versions of the aforementioned can’t save you, either. Nothing that shows that you watch TV or read gossip on the Internet. You have a reputation to protect, don’t forget.
Show off where you can
Showing off can be a great way to extend your reputation. Just do it the right way.
Jeff Tweedy in a Nudie suit. This works because those things are expensive and can be hard to come by. Plus, Wilco, though well known, are respected and wrote some albums that are not to be fucked with, not even by the most indefatigable yawner.
Jeff Tweedy in a birthday suit. You’ll just end up looking like yourself naked more than anything else.
Evil twin or less talented sibling
It can be great to dress up as your favorite performer, but why not add a twist. Be that person’s evil twin or less talented sibling.
The less talented but very competitive brother of Tom Waits. Dresses a lot like Tom, but croons mostly about the economy and corporate life and how great it is to have a job with benefits.
The Bacon Brothers. They’re already both in the spotlight and are equally less talented to each other. (Note that this costume can be saved if you dress up a third Bacon brother who is talented, which spins the whole costume idea on its head.)
Have a backstory, but keep it simple, stupid
Character development is great, but an elaborate backstory will kill any costume along with your chances of bringing home a sexy witch (see Appendix). Costumes should be self-explanatory, unless you’re going for a healthy dose of obscure. The iceberg’s tip should tell you nearly everything about what’s happening underwater.
Be an evil twin and say, “I’m so-and-so’s evil twin.” Boom. Done. You and the sexy witch have a great time until you spill your drink on her.
If your interaction goes anything like this, you’re wearing a spoiled concept. “Oh cool. Orson Welles,” says the sexy witch. “Sort of,” you say. “It’s true that I’m Orson Welles, but that’s not all. I’m actually Orson Welles as the voiceover for that planetoid robot in the Transfomers movie—the heartbreaking cartoon version from the ’80s. You’ll notice that I’m not dressed up as Unicron, but instead as Mr. Welles warming up on his way to the recording studio to do the voice.” Sadly, you won’t even have the chance to spill your drink on her because before you’ve gotten to the word planetoid she’s already turned away to speak to someone who’s really pulling off the Deuce Bigelow costume.
It’s always a good idea to dress up as Rick Moranis. This doesn’t just go for Halloween.
Rick Moranis from any point of his career.
Don’t not dress up as Rick Moranis.
Appendix: For ladies only
Here’s a special tip for the the ladies: Put a cat-ear headband on and you’re now a sexy version of whatever you are.