In 2008, we asked our staff and readers to share their most memorably successful Halloween costumes. So it seems only fair to complete the circuit this year by asking the opposite: What was your worst Halloween-costume failure?
I think I’ve been doomed to Halloween failure ever since I was an infant and my mom tried to sew me a pumpkin costume, realized she couldn’t sew, and just basically wrapped me in some orange cloth. My first major Halloween fail was the year I decided, last-minute, to go as Beetlejuice, but failed to make my hair stand on end, so as a last resort, resorted to dressing/painting half of myself in white, half in black. One year I was invited to Leonard Pierce’s “conceptual” Halloween party and tried to go as “pretension,” but I think it just looked like I was wearing my own clothes and carrying a Proust book. More recently, when invited to a ’70s-themed party, I thought it would be cute to dress as Annie Hall, but then was just miserable and felt dumpy and ugly compared to all the other girls in their platform heels and big sunglasses. I gave up a few years ago when I was invited to a wedding-themed Halloween party and I was extremely pleased with my idea of going as a drunk bridesmaid. I got to re-use a pricey bridesmaid gown, messed up my hair and mascara, and carried a beat-up bouquet of roses and an empty champagne bottle. First of all, any costume that involves carrying a prop is a drag: two is just folly. But basically, I was just a sober girl who looked drunk in a Vera Wang gown: I don’t know if people even knew I was in costume. I’m done. My favorite costume the last few years is “Lady who stays home and eats candy.”
The conceptual Halloween party! That was fun. Weird how people do those snotty, clever costume ideas every year, until you ask them to do it, then everybody gets self-conscious about it. Anyway, my own story is much, much, much worse, although in my defense, I was just a kid, with a limited understanding of international geopolitics and history. I don’t remember how old I was, though my depressingly comprehensive memory of Marvel comic books of the 1970s tells me I was between 8 and 10, and I decided that, after years of my mom picking my Halloween costume, I was going to do it myself this time. (Although of course she’d have to do all the heavy lifting of making the damn thing.) So, naturally, like any other red-blooded American boy of the time, I decided I would go dressed as the horrible anti-Semitic Nazi supervillain The Red Skull. I swear I had no conception at all the horror with which Hitler and his gang of lunatics were viewed; I just thought the Red Skull was an awesome-looking supervillain. So mom bought me some makeup and a bald cap, and did my face up like a skull dyed red. She picked out some clothes and made a rough approximation of the green jumpsuit the character was wearing at the time. She even found a toy version of a broomhandle Mauser. She drew the line, however, at stitching a huge swastika on the chest of the costume; I had no idea why, and in a fit of unbelievably clueless I’ll-show-her-ism, I snuck a laundry marker out of the house and drew it on myself. So off I went to a costume party that all my friends and their parents would be attending, completely unable to fathom why I was getting so many curious looks. (I thought it might be because of the toy gun, and kept assuring people it wasn’t real.) Now, I know what you’re saying: “Leonard, you goddamn moron. Child or not, you wore a Halloween costume based on the worst genocidal murderers of the 20th century.” That’s a worst-case scenario. To which I respond: “Worst case, eh? What if I told you it was a church-sponsored costume party?”
I’m so god-awful crappy at Halloween that I haven’t even bothered with a costume for at least five years. The last time I can remember wearing one was either sophomore or junior year in college, when I either gave it an honest shot, or thoroughly revealed my ineptitude by going as “Halloween Surprise.” You know, a costume all thrown-together and of dubious quality, like a Meatloaf Surprise. I wore a cape (a honey-mustard-colored bedsheet) and a bike helmet, to which I thumb-tacked a bunch of assorted photo prints. It’s the kind of costume that says “Hey, I tried, barely, and I’m still kind of attracting attention to myself through idiocy, so please allow me to attend Halloween parties on a technicality.” Stupid. Oh yeah, and the year the Coneheads movie came out, you could buy rubbery cone-scalps to wear for Halloween, and since I was a little kid, my dad and I went together. I thought it was awesome, but some people taunted us: “What’s that, a condom on your head?”
One of my cousins was born on Halloween, which led to a lot of costume-required birthday parties growing up. I think I was 14 the year my brother decided to go as Kabal from Mortal Kombat 3. I had a navy-blue leotard from an old dance costume lying around, so I decided to go as another character from the MK universe, Kitana. I made matching armbands and a ninja mask and even fashioned her attack fans out of popsicle sticks and white canvas. For something I threw together in a couple of days, it looked pretty good. But sometime between finishing the costume and going to the party, I realized that I didn’t want to spend the day wearing nothing but a leotard around my extended family. So I put on a trenchcoat. Aunts and uncles repeatedly asked me what I was supposed to be (my brother, in his creepy homemade mask, was just another monster to them), but I steadfastly refused to show anyone my costume. The trenchcoat stayed on and closed the entire time. Lesson learned: Never let a good idea overshadow your comfort zone.
It was college, sophomore year, and—no, wait. First thing: I love Halloween. Always have. And I’ve always wanted to wear great costumes, but I’ve never been able to top the Adam West Batman costume my mom made me when I was 8. But it was college, and I’d been invited to a party, and there-was-a-girl, so I developed Ambitions Above My Station And Ability. I decided I wanted to go as Batman’s arch-nemesis, The Joker, and since this was almost a decade before The Dark Knight came out, I wouldn’t have been a complete cliché; when I smile too widely, I kind of look like Jack Nicholson in the Tim Burton Batman, and I also have a propensity for terrible, terrible jokes. A friend of mine was headed to the costume shop for supplies, so I asked him to get me some green hairspray and white makeup. The hairspray he picked up was fine, but he got regular pancake makeup instead of the white stuff, so when it came time to put the outfit together, I was just a guy in a black shirt, purple tie, green-blonde hair, and lipstick. I looked like the world’s worst David Bowie impersonator; actually, I looked like I’d made out with the world’s worst Bowie impersonator, then stole his clothes. I went to the party anyway, because I was at a point in my life where I thought being stubborn and grim was the same thing as being likeable. I showed up two hours before the party started, and instead of walking back home to wait (I lived five minutes away), I walked up the street and found a bus stop and climbed up a tree and waited. I didn’t have a watch, so after I couldn’t take it anymore, I walked back to where the party was, to find that I still had an hour left to kill. So it was back to the tree. Finally I timed it right (and did I mention that the girl I liked was throwing the party, so each time I showed up too early, she was the one to tell me it hadn’t started yet?), and I lasted maybe 20 minutes. None of my friends were there, everybody was drinking, and I kept waiting for someone to ask me what I was dressed as, but nobody did. I probably didn’t have my best face on by then. There was a big scene with the girl—I remember her being frustrated with me in a way that a lot of people were frustrated with me back then, and I remember being oddly happy that I’d made any kind of impression at all. She was dressed as a pixie, and at one point she said, “I’m sorry, my wings are in the way,” and I told her, “Your wings always get in my way,” and I thought that was terribly profound of me, although I mostly muttered it. Then I went home and washed everything off. I’ve gotten better at costumes since then, but I think I’ll never have as much fun with it as I want to, because in real life, I have a hard time pretending I’m anyone else.
In the fall of 1995, being a junior in high school, I thought I’d be “subversive” and “edgy” by dressing up as O.J. Simpson attorney Robert Shapiro. It was an easy costume, consisting of a suit with a bloody glove hanging out of one pocket. Of course, this came only weeks after the controversial verdict in Simpson’s murder trial was announced, and emotions were still raw, as much of the division over the verdict was along racial lines. Not only did my costume require explanation to almost everyone I encountered, it deeply offended them, especially in the predominantly white North Alabama city I grew up in. That night, I learned, as David Letterman had told Howard Stern, there’s nothing funny about double murder. Halfway through the night, I stopped at a friend’s house, ditched the suit, grabbed a blue-and-green-striped sheet, and spent the rest of the night as a half-assed ghost.
There was a period where I’d go nuts getting my Halloween costumes just perfect. I scoured thrift stores one year to find the perfect sweater vest to wear as Ferris Bueller—and I found it, a leopard-print one that looked almost exactly like the one from the movie. It was awesome, even if no one got it. The next year rolled around, and deciding to be just as profound, I went with the obvious choice: Earl from My Name Is Earl. In hindsight, it was a dumb costume idea to begin with, but for whatever reason, I felt it was the pinnacle of pop culture at the time. (Probably because they drank Heisler beer on the show—a brand seen often when someone doesn’t want to seek out an actual beer sponsor.) So I once again scoured the thrift stores looking for the perfect flannel shirt, bought boots that matched Earl’s, grew out my hair to the swoopiest of swoops so I could style it like his, bought a fake mustache, and hit the streets… where I was greeted with not cheers or jeers, but endless shouts of, “Hey, Borat!” Somehow I had forgotten about the most obvious mustachioed disheveled guy. Somehow I had forgotten that absolutely no one watched My Name Is Earl. Then my mustache fell in my drink.
I tend to put tons of effort into my Halloween costumes, so for me, a costume failure is when I just totally half-ass it due to time/budget constraints, like when I dressed all in black and went as an “invisible pedestrian,” or the three-year span where I was a pirate because I already had the costume. (Though one year I added headphones, so I was a “music pirate.” Clever girl!) But generally, I spend a lot of time and effort putting together complex, often cumbersome costumes. They’ve pretty much all gone over well, but a couple years back, I found myself burned by my own ambition.
For years, I’d been wanting to get a bunch of friends together and go as different colored troll dolls, but no one wanted to commit to the naked part of the equation. So finally I decided “Fuck it, I’ll do it on my own.” I procured a nude body suit—American Apparel, you’re still good for something!—and spent hours dying and spraying a long blond wig into a massive, 2-foot-tall blue troll-doll wig. An oversized blue gem on my tummy and bam, Treasure Troll. Then, of course, I had to go out in this getup, first to a concert, then to a house party. Luckily, it was warm, so I didn’t need a coat, and if there’s one time you can ride the bus while fake-naked, it’s Halloween night. However, the night of debauchery took its toll on both my wig—which was a terrible, terrible idea in hindsight—and my faculties, and I ended up having to crash at the house I was at. Remember how I said Halloween night is the one time you can ride the bus while fake-naked? Well, topping the list of times you shouldn’t ride the bus fake-naked is at 8 in the morning, which is exactly what I had to do the following morning. Since my wig and tummy gem had long since been sacrificed to the party gods, I was left to ride home covered with only my nude bodysuit and the stink of shame.
Halloween is always a challenge for me because I maybe spend too much time on the Internet, and thus have become unable to separate “popular on the net” from “popular with the masses.” Thus my worst costume happened in 2003, when I went as very tan, Tinkerbell-toting Paris Hilton, then just a Gawker and Internet “celebrity,” and thus not known to basically anyone at the time. (The Simple Life wouldn’t première until that December, and 2004’s One Night In Paris was but a glint in the collective population’s eye.) I went to college at Ohio University, which becomes a drunken mecca for 100,000-plus Midwestern kids every Halloween, and thus becomes a hotbed of both sexual harassment and slutty devil, cat, and rabbit costumes every year. (I know, I know. Not that Paris is that much different. I was young and naïve.) I was meeting some friends at a bar and decided to cut down a side street so as to miss the mobs of people collected on the main drag. This dude started heckling me from a porch, slinging filthy come-ons and “You want some of this, baby” dick-grabbing. Upon closer look, I realized it was a dude I’d known casually for maybe 10 years, as we’d gone from elementary through high school together. His mom was the high-school secretary, even. He didn’t recognize me, but the second I realized it was him, I laid into him, asking how his mom was, how his sister was doing, and so on. It made me feel better at the time, but now I just wish I’d been a ghost or something, or maybe Clarissa from Clarissa Explains It All, my costume from the year before. Oof.
My biggest costume failure was also the last time I wore a Halloween costume, which was about 10 years ago. (I know. I’m no fun.) I decided to go as a late-night horror-movie host of my own invention. So I dug out my mortar board and robe from graduation—don’t know why I still had them—painted my face white, and decided my name was Professor Nightmare. Try explaining that over and over all night. Fun? Nope. Heck, half the time I had to explain what a late-night horror-movie host was to the friends of my five-years-younger-than-me future wife, who never grew up with a Dr. Creep or Svengoolie on their local television stations.
2001 offered a rare chance to elevate the normal audacity it takes to dress up like a recently deceased celebrity, and take on a national tragedy instead. Being a total shithead at the time—but not a complete asshole—I steered clear of anything to do with 9/11, but somehow thought it was cool/funny to dress up like anthrax. This involved making a huge letter out of cardboard, addressing it to Senator Daschle, creating a sweet “stamp” from a print out of the cover of Anthrax’s “I Am The Law” 12-inch single, and carrying around a bag of flour for throwing at people. Not surprisingly, wearing a five-foot-wide piece of cardboard around your neck is a good way to piss off people at bars. But I think I was genuinely shocked when a dude walked right up and punched me in the head. I couldn’t believe he was still offended, even though I had shown the decency of not mocking a national tragedy by opting instead to mock a much smaller tragedy. I realize now that I probably needed a good talking-to, but the guy didn’t have to hit me.
Sometimes you’re caught on Halloween night without a costume and you’re miraculously able to pull something decent out of your existing wardrobe. I definitely did not accomplish that the Halloween of 1997, when I was summoned at the last minute to a costume-mandatory Halloween house party. I’ve never been much of a Halloween person—social anxiety plus crowds of people you can’t recognize equals severe psychic trauma—but I decided to be a good sport and throw together a last-minute costume. I rummaged through my closet, grabbed an old parka, a vintage Fred Perry, and some tennis shoes and decided to dress as Jimmy The Mod from Quadrophenia. (Or more of a generic mod, really.) When I got to the party, though, my costume didn’t get a single comment or glimmer of recognition—that is until toward the end of the night, when one of the hosts came up to me and said, “You know, you could have at least tried to come up with a costume.” Granted, she had a point: That was pretty much how I dressed every day back in 1997. Like I said, Halloween ain’t my strong suit.
I’m one of those people who irritates other people in my age range by not really giving a shit about Halloween. In college, I put the bare minimum of effort into costumes, usually just slapping on a “clever” nametag (though one year, I scrawled Bible verses on two pieces of posterboard and went as a prophet of doom, which was a hit). Since then, I buy a bag of candy in the odd event that neighborhood kids drop by, but I mostly just don’t get the shift the holiday’s undergone from a fun and spooky night for kids to a chance for adults to get trashed and hook up. Couldn’t we do that any night?
Lest I sound like a buzzkill—I am!—I should probably explain that when I was 4 or 5, we started attending a fundamentalist Christian church, where the pastor spent much time haranguing us about the dangers of letting children celebrate Satan’s night. My parents, not wanting to commit my sister and my souls to the devil, but also not wanting to give up the yearly trick-or-treat visits to grandparents and teachers, were caught in a bind. The pastor, recognizing this would be a problem, helpfully explained that kids could come to the yearly church “fall party” (hosted on October 31, of course) dressed as an angel or a Bible character, but while a fair number of girls wanted to dress as angels, I didn’t know anyone who could pull off Abraham or Moses, or had the stones to go as Jesus. This led to a years-long war with my mother over what I could dress as for the yearly school party. Supernatural stuff was out. So was most science-fiction stuff, which meant my fallback of “alien” wouldn’t work. And we also weren’t going to spend money on Halloween and encourage the celebration of the holiday in the general populace. Whatever costume I wore would be from shit we had laying around the house. One year, my sister went as a clown and I went as a scarecrow (the closest to “scary” I could get) but we both used the big bag of mid-20th-century clown garb we had somehow inherited from a recently deceased great aunt, so we just looked like disturbing clowncrow hybrids.
By the time I made it to fourth grade—my last year of a school Halloween party, thus, the last year my mom was going to bother fighting me over this costume thing—I thought about a way to both play by the rules and pull off a costume my friends would think was awesome. Finally, I settled on a gorilla. No one could claim a gorilla was supernatural or sci-fi, but it would also be, in my mind, sufficiently scary. Here’s the thing about gorilla suits, though: They cost hundreds of dollars. And no one makes child-sized gorilla suits. Add in to that my family’s decided opposition to monetary support of the holiday, and you had a recipe for my mom—already too stressed out from all of this fighting with her normally good child and short on time from a late harvest that year—to just say that eternal phrase of mothers confronted by too-ambitious costume ideas, “I’ll do my best,” and half-ass it. Which is how I came to parade around the halls of my school dressed in black pants, a fur coat inherited from another recently deceased great aunt (which still smelled of old-lady perfume), and a terribly Xeroxed picture of a gorilla from the cover of an old issue of Zoobooks rubber-banded to my face. When I didn’t have to dress up the next year (or ever again), I was relieved.