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And Now, Your Worst Halloween Costume Stories

Illustration for article titled And Now, Your Worst Halloween Costume Stories

We were living in Chicago when I was six, and I chose to be a ghost for Halloween. I made the costume myself, because cutting two holes in a sheet seems like an easy task. Of course, I had to cut a third eyehole, because my first two were off-alignment. I also failed to consider the fact that a ghost costume has nothing fastened to your body. You're basically relying on the top of your head to provide enough friction to keep the eyeholes in place, which is not good. We went up and down the stairs of our apartment building all night, going from door to door, and that fucking sheet must have come off me 90 times. I nearly tripped and fell to my death. I will never be a ghost again. Not for all the Butterfingers in the world.

But my travails are piddly shit compared to some of the stories you're about to read. A Halloween costume can go wrong in so many ways, and our readers have gone to great lengths to explore that wrongness. Behold …


Halloween 2003 took place while I was in third grade, and at that time in my life (and today) I was a huge sports fan and a huge fan of jerseys in particular. My birthday was earlier in October, and I had received the only two things I wanted: A LeBron Cavs jersey and a Melo Nuggets jersey (remember, this was their rookie years—the hype was through the roof).

Anyway, I decided I wanted to be LeBron James for Halloween. Rather than tell me it was silly and buy me a Superman costume or something—you know, normal—my mom decided it would be a good idea to go all out on this costume. I had the jersey and a Cavs hat (which my mom glued printed-out $100 bills to, for some reason) and the kicker: brown face paint. My mom probably didn't know any better, but she helped me dress up for third grade Halloween in brownface. So there's that.

So Halloween comes around, and my elementary school had a "Halloween parade" where all the kids would go out and walk around the playground in their costumes, and parents would watch it, and it was great fun. Well, Halloween that year happened to be warm and sunny, and it ended with me walking around the playground as my retrospectively wildly insensitive face paint melted and ran down my face and onto my jersey, arms, hands, etc. I went out as James Bond (wore a suit and carried a cap gun) later that night. This was in suburban Philly, and my mom is Canadian, fwiw. Not anyone's best efforts.



I went to the bars as a blind ref for Halloween last year, because I'm a dumbass. While on my way there I crossed paths with an actual blind kid and his mom. I felt like the biggest dick on the face of the Earth.


This monstrosity was the culmination about about four nights of work while watching the Red Sox win the World Series in 2007. To say I was drunk when I made it is a massive understatement. The nights making this consisted of drinking about 12 beers and remembering 10 in that it was almost Halloween and I should finish my "Grimace" costume, and then hastily constructing a cardboard body and taping purple hand towels bought in bulk from a sketchy home goods store in Queens. Pretty sure the spray paint I used for the "mouth" was found when we moved into the house I was renting with my dirtbag friends that we found out used to be a drug den. Sometimes it's amazing I am still alive.

Illustration for article titled And Now, Your Worst Halloween Costume Stories


For a costume in college, I needed glasses to tie it together. Being lazy and in a rush, I grab a pair from the drug store without paying any attention to the strength of the prescription. I needed "nerdy," and they were thick and did the job perfectly. I get housed and leave the glasses on all night.

For the next four days, I had a splitting headache, and my eyes felt like someone had run over them. I thought I was roofied, but it was all because they spent hours straining under a prescription meant for a nearly blind person.

Do not fuck around with real glasses.


Sophomore year of college, a couple buddies and I dressed up like Average Joes vs. Purple Cobras from the movie Dodgeball. It was lame, but it was cheap. Unfortunately, it was also cold as tits outside, and I ended up wearing full-length compression pants (NBA players make it look BAWSE; I make it look like a lumpy sack of potatoes).

At some point throughout the night, someone gave me a king-size pack of M&M's (more lumps!). I opened them but didn't finish them. Without pockets, I decided to stick them in my compression shorts against my bare ass. A little foreshadowing here: This is a terrible idea.

Many drinks later, I end up going back with some girl to her dorm room. We immediately hit the sheets. I give Ol' Johnson two tugs and I realize he was dead on arrival. I leave my pants on and play it off like I'm too tired. I write it off, roll over, and pass out.

I awake to some girl I am vaguely familiar with screaming at me, "Get the fuck out of my room, you shit in my bed." I took her word for it and headed for the door. I went to the bathroom to clean up the best I could. When I peeled down the compression pants, I found a pack of M&Ms that had been liquefied by my ass cheeks.



There was one year where we tried "Terry Schaivo on a gurney." You push her up to people's doors and ask if they wanted to feed her or pull the plug. It got tiresome after about three visits.



A friend of mine, when he was 12, went as Michael Jackson ... except he went as half-black/half white Michael. He painted half of his face black and one arm black, and carried around a baby doll. He made it about six houses before one of his best friends' mothers saw him and was outraged. She brought him home and yelled at my buddy's parents.



When I was like 24, I dressed up as Britney Spears from the "... Baby One More Time" video. Tied-off dress shirt, short tennis skirt, thigh-high socks, and a wig to cover my shaved head. I wasn't in the most amazing shape of my life, but I played hockey, so I at least had great legs. The bottom half of me definitely looked a lot more fuckable than the top half.

The end of the night comes, and I'm ridiculously drunk, riding in the back of my friend's car, when I decide that I'm not gonna be able to make it home without puking all over his seats. It's 3 a.m., so he pulls off to the side of the highway so I can unleash the devil over the side of the overpass.

As I'm leaning over the railing, just about done puking, a tow truck pulls up and the driver gets out to ask if I need help. All he could see was the skirt and knee-highs, so I guess he thought he was going to be saving some purdy little thang's night. Until I leaned back over the railing, face red and sweaty from throwing up, hairy chest showing, my hat and wig in the back seat of the car.

"I'm good, man," I say, as I wave him back to his truck.

I can only imagine what went through his mind in that moment, but I suppose the look of horror and dejection on his face gave me a pretty good idea.



My mom made me a cat costume when I was a kid, and I cried about stepping on the tail with every other step while trick-or-treating. She then cut off the tail when we circled past the house, and I cried some more about that.



Freshman year of college.

A kid on my floor wants to be the Joker. Now, obviously this is a good idea, since Heath Ledger has only been dead for roughly seven months, and "Who the fuck else is going to dress up as the Joker? That would be in poor taste."

Now, me being the asshole that I am, decide to take this one step further. I am going to be Heath Ledger's empty pill bottle. Long story short, I take a 50-gallon trash can and outfit it to look like a giant pill bottle, and wear it like that dip shit barrel man that used to go to Denver Broncos games. As we're walking around looking for a party (mind you, we're stupid fucking freshmen, and nobody wants freshmen at their house parties), I get people throwing beer on me from their cars, because "Fuck you, that's not a funny costume!" At this point, I begin thinking this might be a bad idea.

We walk into a party, Joker first, and everyone thinks the Joker costume is incredible. The kid went to great lengths to make it look as real as the movie character as possible. I follow this kid around all night, and eventually I get punched in the face, for "being an insensitive piece of shit."



When I was a kid, I was into the Universal monsters, especially their yellow-shirted Wolf Man. When I decided to go as the Wolf Man for Halloween one year, my dad helped as best he could: by buying hair weave and gluing clumps of it to my face and hands with latex. I spent my trick-or-treating time explaining what I was dressed as, and trying to hold the weave on my face.



Every year, I wait until the very last second to come up with a costume. Like 25 minutes before a Halloween party and I haven't bothered to even think of a costume yet.

One year, I threw together a bunch of those long cardboard pepsi boxes on my head, arms, and legs (my roommates drank a lot for some reason, fuck them, Coke Zero 4 lyfe), then put a piece of cardboard on my chest and wrote, "Optimus Prime."

The next year, I was even lazier and took a piece of paper and wrote "Clever Girl" on it. An obvious Jurassic Park reference. No one fucking got it, and I felt like a complete asshole.

I also just realized I don't have a costume for tomorrow, fuck.

Drew Magary writes for Deadspin. He's also a correspondent for GQ. Follow him on Twitter@drewmagary and email him at You can also order Drew's book,Someone Could Get Hurt, through his homepage.


Image by Jim Cooke.

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