Finding your inner Macaulay Culkin: 17-plus memorable TV Halloween costumes, and what they say about their wearers

1. Jim as “Three-Hole-Punch Jim,” The Office
The staff at Dunder-Mifflin loves Halloween, and they make a big show of it every year. In fact, they love it so much that some of them break out costumes for a celebration of the Hindu holiday of Diwali, where Michael and his girlfriend Carol come dressed as Michael’s papier-mâché twin and a slutty cheerleader, respectively. Other favorites throughout the show’s six seasons include Meredith as Sookie from True Blood, Jim as “BookFace” (a Facebook concept that backfires), Pam as Charlie Chaplin (or, without the hat, Hitler), and several folks as The Joker from The Dark Knight. In many cases, the choice of costume says a lot about the person wearing it, and there’s no better example than “Three-Hole-Punch Jim” from the show’s first Halloween episode in season two. Taping three circles of black construction paper down his usual white button-down shirt, Jim’s simple costume typifies the apathy and too-cool-for-school attitude that separates him—or that he thinks separates him—from his officemates. It’s simultaneously ingenious in its minimalist wit, and a little dickish.

2. Bart as “Alex DeLarge,” The Simpsons
Of course Bart Simpson would dress up as Alex, the codpieced, bowler-and-cane-sporting antihero of Stanley Kubrick’s A Clockwork Orange. While his peers roll with more predictable, age-and-character-appropriate costumes—Lisa as the Statue Of Liberty, Milhouse as Radioactive Man, Nelson as a pirate, and poor Martin as Greek muse Calliope—Bart chooses the iconic symbol of rebellion and criminal mischief. It’s one of several Clockwork Orange references the show made over the years—in one episode, Lisa’s electroshock experiments on Bart cause him to quake before a pair of cupcakes like the reprogrammed Alex does before a woman’s breasts in Clockwork—and a strong suggestion of how much Bart slips past parental supervision.

3. Xander as “Soldier Guy,” Buffy The Vampire Slayer
In “Halloween,” the sixth episode of Buffy’s resurgent second season, a diabolical curse causes Sunnydale’s trick-or-treaters to truly become whatever their costumes reflect. Which is significant, since the protagonists have all chosen their costumes to reflect something they wanted to be in the first place. Shy Willow covers herself with a sheet and hides as a ghost. Buffy, tired of playing the tough tomboy, flounces it up as an 18th-century English noblewoman, and is subsequently rendered helpless. (Facing danger, she faints; later, she confuses a car for a demon.) That leaves Xander a rare opportunity to save the day. Suffering from an earlier ego-blow when Buffy saved him from a bully, he tries to connect with his inner macho (yet continues to be both cheap and half-assed) with a $2 “Soldier Guy” costume, but winds up as a capable military man, fending off beasties with a fake M16 (“big noise scare monster”), handling triage, and leading kids to safety. It’s clever enough as a standalone conceit, but Xander’s “Soldier Guy” instincts linger even after the spell has been broken, and they come in handy later when a Scooby operation needs a little military discipline. All of which gives Xander a much-needed competency upgrade as the series keeps getting darker and more dangerous.

4. Ted Mosby as “The Hanging Chad,” How I Met Your Mother
The first-season episode “The Slutty Pumpkin” was an important one for How I Met Your Mother. Ted Mosby was to be the series’ centerpiece, but the show hadn’t revealed much about him yet, other than his desire to find the girl he would eventually marry. In “The Slutty Pumpkin,” Ted deals with disappointment; he waits at a Halloween party for a girl he met the year before, and she fails to show. Adding insult to injury is Ted’s costume—a hanging chad, essentially a huge piece of cardboard around his neck. Given that the episode aired in 2005, it’s horribly dated, yet Ted Mosby is the kind of guy who’d wear the lamest Halloween costume imaginable, while thinking it was unbearably clever. That hanging chad costume represented the early stages of How I Met Your Mother’s humor: sweet, sometimes sappy, but always unabashed. And from a costume standpoint, Ted’s version of the hanging chad is clear without being too obvious, always a smart choice on Halloween.

5. Dick Soloman as “Pirate”: 3rd Rock From The Sun
The ’90s cult science-fiction comedy 3rd Rock From The Sun always got a lot of mileage out of holiday episodes, as the Solomon family proved constitutionally incapable of wrapping their heads around the various complicated rituals involved. Some of the best shows in the first few seasons are holiday-themed, including the family’s first Thanksgiving, which they misinterpret as a sort of turkey apocalypse. The show’s first Halloween episode includes are all sorts of fish-out-of-water gags: Dick eats the guts of the pumpkin he’s carving. Sally and Tommy, in Sonny and Cher drag, turn trick-or-treating into a sadistic military exercise. Harry unsubtly dresses as an alien. Dr. Albright’s Wizard Of Oz Dorothy costume is mistaken for a Nancy Kassebaum outfit. But the best gag involves Dick showing up at a Halloween party also attended by his physician, who mortally terrifies him. Dick’s costume, a pirate captain, allows the show to set up one of TV’s best can’t-believe-they-got-away-with-it gags: “Where are your buccaneers?”, the doctor asks. Dick replies—in grand John Lithgow ham delivery mode—“Under my buccan hat.”

6. Cerie Xerox as “An Italian Senator”: 30 Rock
Even before the “Stone Mountain” episode that finds Frank, Lutz, and Toofer trying to swing an invitation to Gay Halloween, viewers catch a glimpse of some of the other TGS players in costume. To illustrate how disastrous Kenneth’s parties are, a flashback reveals him decked out as Austin Powers, a good 10 years past the social relevance of such a costume, and a game Liz Lemon desperately trying to play along in an ever-so-slightly less dated Harry Potter outfit. But for Gay Halloween—the sexiest Halloween of them all—TGS assistant Cerie goes all out: Donning a skimpy bikini, she says she’s dressed as “an Italian senator,” referencing the Italian parliament’s occasional infiltration by porn stars. In a webisode that aired the same week, Cerie modeled more costume ideas, from “sexy sheriff” (short-shorts and bustier with a star on the chest) to “sexy writer” (short-shorts and bustier with a pencil behind the ear) to “sexy Liz Lemon” (short-shorts and bustier with glasses and a big appetite). For people who loathe the recent sexualize-everything trend in Halloween costumes, it was a nasty bit of satire, and for everyone else, it was three minutes of Cerie in a revealing outfit.

7. Derek as “A Straight Person”: Parks And Recreation
By coincidence or design, 30 Rock and Parks And Recreation both broadcast an episode singing the praises of “Gay Halloween” on the same night. Perhaps it was an NBC initiative, like Green Week. Whatever the case, P&R’s Halloween episode, “Greg Pikitis,” gives most of the cast a chance to strut their costumed stuff: Ann appends a “Raggedy” to her name, Ron Swanson goes for the classic pirate outfit, Tom Haverford blows the doors out with a T-Pain ensemble, and much to Ann’s dismay, all the doctors she works with show up dressed as doctors. The best costume of the night, though, belongs to April’s gay boyfriend Derek, and is introduced with a perfect visual joke: Clad in Dockers, a blue Arrow shirt, and loafers, he at first didn’t seem to be wearing a costume at all. When questioned, he says he’s dressed as “a straight person”—and, to prove his point, up walks the indisputably heterosexual Mark Brendanawicz, wearing exactly the same thing. It’s a five-second gag, but it’s so smoothly delivered as to be unforgettable.

8. Britta Perry as “A Squirrel”: Community
When Community took its first shot at the venerable Halloween episode tradition, everyone showed up in costume, but it was easy not to notice, because Abed’s hilarious, dead-on impersonation of Christian Bale in The Dark Knight dominated the proceedings. There were plenty of other good ones, including Pierce as the Beastmaster and Shirley as Harry Potter, although everyone mistook her for Urkel. But perhaps the most revealing costume was the simplest: Prickly, easily offended Britta shows up in a baggy, shapeless squirrel costume with a huge, awkward tail. She intellectualizes it by claiming it’s a reaction to girls using Halloween as an excuse to dress up like sluts, but the truth may be deeper than that. The costume was suggested by Gillian Jacobs, the actress who plays Britta, and creator Dan Harmon explains on the audio commentary for the “Introduction To Statistics” episode, “At first, I know, a lot of people didn’t get Britta’s character,” he says, “but here’s where you really understand it: Her daddy didn’t take her to the zoo.”

9. Bill Haverchuck as “Jaime Sommers”: Freaks And Geeks
Halloween is a strange time for adolescents. Kids on the cusp of teenhood usually feel too mature to dress up and go trick-or-treating, but too socially awkward to go to the cool kids’ dress-up parties. No show was better at portraying that muddled haze of adolescence than Freaks And Geeks, and its third episode, “Tricks And Treats,” found the geek contingent futilely trying to recapture the freewheeling fun of their younger years by dressing up and going door-to-door in search of candy at an age when most sensible kids are sneaking swigs out of their parents’ liquor cabinet. The show also nails another common adolescent disaster: the costume choice that’s so terrible, everyone knows it but the guy wearing it. In this case, the guy is scrawny, oblivious Bill Haverchuck, who can’t think of anything more masculine than going in drag as Jaime Sommers, the Bionic Woman. The scene where he psyches himself up in the mirror is painfully funny, and it segues into a wonderfully horrible situation where he sees himself as the epitome of cool, while everyone else just sees a gangly 13-year-old boy in a dress.

10. Carlton Banks as “Macaulay Culkin”: The Fresh Prince Of Bel-Air
Playing on racial stereotypes is always tricky on TV. Nowadays, the go-to joke for writers looking to make a point about cultural co-option is to have someone painfully white act ’hood, but back in the early ’90s, the gag was to present a black character as immersed in the nerdiest white culture. The epitomes of this type were Family Matters’ Steve Urkel and The Fresh Prince Of Bel-Air’s Carlton Banks. In keeping with the television trope of having Halloween costumes reflect a character’s inner life, Carlton appears in “Hex And The Single Guy” dressed as his idol, Macaulay Culkin, a joke that packed a lot more punch when Culkin was primarily known for making goofy faces in Home Alone and being America’s favorite blonde kid from the suburbs, and not for making movies like Party Monster and taking shitloads of clonazepam. As with Woodstock, you really had to be there.

11. Dave Nelson as “A Pretty, Pretty Lady”: NewsRadio
The masterfully crafted sitcom NewsRadio knew how to play with its audience’s expectations just enough to deliver a payoff with the most laughs possible. In the “Halloween” episode, Mr. James disinvites the WNYX staff from his annual costume party because they have a history of not taking it seriously. So when Dave promises to wear the most outrageous thing imaginable to inspire everyone else, it’s not too much of a stretch—especially to viewers familiar with his extensive drag work in The Kids In The Hall—to predict he’s going to show up dressed as a woman. What happens from there, though, is a testament to the show’s determination to take standard ideas into hilarious new directions. Not only does the outfit upstage the previous most memorable costume—Matthew’s “motorcycle enthusiast,” or as Joe puts it, “gay biker”—but it infuriates Lisa, whose dress Dave is wearing. And while trying to put things right, Dave learns that isn’t mad that he took her dress without asking, she just hates that he looks better in it than she ever has. It’s a perfect example of the classic setup, unexpected twist, and perfect execution that made NewsRadio so great.

12. Hank Venture as “Batman”: The Venture Bros.
Hank’s Batman obsession has proven troublesome to the Venture family on more than one occasion. (It cost him his life once, but that was back when Hank clones were in plentiful supply.) But never did Dr. Thaddeus Venture more strongly disapprove of his son’s Bruce Wayne fixation than in the “Love-Bheits” episode. Before being captured by Baron Ünderbheit, the Ventures are on their way back from a costume contest, where they lost Best Group Costume thanks to Hank’s insistence on dressing as Batman instead following the Star Wars theme everyone else favored. It turns out it wasn’t even the first time: The Ventures had previously appeared as “the cast of The Wizard Of Oz… and Batman” and “the members of the rock group Kiss… and Batman.” Hank has the patter down (he quotes Frank Miller’s The Dark Knight Returns while in costume), but he doesn’t quite have the moves; he blows a chance to rescue his family with Batman-style heroics when his tongue gets caught in the mouth slot of his cheap plastic facemask. Still, his costume obsession makes it clear how he really wants to see himself: Not as a death-prone spaz, but as a stone-cold bad-ass, worthy of his reluctant mentor/bodyguard, Brock Samson.

13. Cliff as “a funky Groucho witch-type character”: The Cosby Show
Ever the sweater-clad curmudgeon, patriarch Cliff Huxtable has a hard time getting into the Halloween spirit in the Cosby Show episode “Halloween.” But after he equates trick-or-treating with begging, his wife Clair finally convinces him to take their youngest daughter Rudy out to scrounge for candy. Still, he initially refuses to wear a costume. Clair tells Rudy she should make a costume for Cliff, which seems like an innocuous enough project for a small child. But when Cliff finally comes clomping dejectedly down the stairs that night, the full extent of Rudy’s sartorial skills becomes apparent: She’s dressed her dad in some ungodly grab-bag of odds and ends, including a loud plaid jacket, baggy pants, a witch’s hat, and Groucho glasses. One of Cliff’s rules for Rudy and her trick-or-treating friends as he marches them out the door? “While we’re out there, please don’t tell anyone who I am.” Unhappy as he was with the whole concept, though, he was still focused on his family, which was really most of what The Cosby Show was about.

14. Charlie Brown as “ghost”: It’s The Great Pumpkin, Charlie Brown
In 1966, the third prime-time Charlie Brown special, It’s The Great Pumpkin, Charlie Brown, left a lump of angst in the trick-or-treat bags of America’s youth. Charlie Brown isn’t the only kid in a ghostly bedsheet, but of course he’s the only one with a dozen-plus eyeholes cut into it: “I had a little trouble with the scissors,” he glumly explains. Of course he did, as the perpetual sad-sack/goat who generally gets everything a little wrong. When Charlie Brown and crew go knocking on doors for treats, everyone else gets a substantial haul: candy, a cookie, gum, a popcorn ball, even a quarter. Except for poor Charlie Brown, of course, who’s stuck all night muttering the hapless refrain, “I got a rock.” It isn’t just that Charlie Brown screwed up his costume—it’s that he came so close to fitting in, yet remains so far from it. Even as a ghost, no one pays him any respect.

15. Cartman as “Hitler/Klansman” on South Park
“Pinkeye,” from the first season of South Park, is the show’s first Halloween-themed episode. But it set the tone for just how far Trey Parker and Matt Stone were willing to push the level of taste and propriety, and just how aggressively offensive—and oblivious or indifferent to other people’s feelings—Cartman was willing to be. Amid the would-be zombie attack that drives most of the plot, Stan (dressed as Raggedy Andy) and Kyle (as Chewbacca ) meet up with the always-corrosive Cartman, who’s decided to go as none other than Adolf Hitler for Halloween. Things only get worse from that point: Cartman’s costume makes waves at school, which forces Principal Victoria to try some damage control by dressing Cartman as a ghost. Instead, she accidentally makes him look exactly like a Ku Klux Klan member.

16. Hawkeye as “Superman”: M*A*S*H
A lot of the interpersonal tensions that made M*A*S*H so edgy in its early years were resolved by the show’s final season—which is what makes “Trick Or Treatment,” M*A*S*H’s 1982 Halloween episode, more of a warm, weary, character-driven tearjerker (albeit a ghost-story-driven one) than a salvo of wisecracks. The best part of the episode is getting to see everyone partying together in costume: B.J. as a clown, Colonel Potter as a cowboy, Klinger as a gangster, and Major Margaret “Hot Lips” Houlihan cutting loose as a geisha girl. Hot Lips’ sexy garb wasn’t really all that attention-grabbing, though; after all, before finally giving up on trying to get a Section 8 as a transvestite, Klinger dressed up as one almost every day of the year. And of course there’s Hawkeye as Superman, reflecting both his inflated sense of self-worth, and his deeply wry sense of humor, which typically has him joking about that self-worth to hide his own fears about whether he or any of his friends are going to make it through the war. Given what he saw on a daily basis throughout the war, no wonder he wanted to dress up as someone invincible.

17-plus. Various, Roseanne
Roseanne is second only to The Simpsons when it comes to celebrating All Hallows’ Eve: over its nine-season run, the series pumped out seven Halloween episodes that treat the holiday with the sort of reverence most sitcoms save for Christmas specials. (Appropriately, the season-four Halloween special was an homage to A Christmas Carol.) The Conner family’s ongoing quest to out-prank and out-costume one another led to several memorable—and frequently cumbersome—getups over the years, including Dan as The Three Stooges, Roseanne as Prince, Darlene as Tippi Hedren in The Birds, D.J. as Hannibal Lecter, and Dan and Jackie as a headless Marie Antoinette. The Conners’ clever, occasionally eyebrow-raising costuming choices hint at the subversive tendencies percolating beneath the family—and the show’s—blue-collar, Middle American exterior.