Halloween is almost here. Time for bonfires, hay rides, and tricks galore. And, when the wind is too brisk outside and the daylight begins to wane, the month of October makes the perfect time to nestle down with a hot chocolate and a comforting TV show. When it comes to comedy shows commemorating the holiday, many have added to the canon of Halloween specials at least once. But the shows that commit to one episode a year, letting out a writers’ room of pent-up desires to go big and wacky at least once per season, are considerably rarer. The Simpsons with their “Treehouse of Horror” specials and, recently, Brooklyn Nine-Nine’s Halloween Heists are exceptions to the rule.
Around the time The Simpsons began their yearly anthologies of terrifying tales, a working-class family from the fictional Midwestern exurb of Lanford, Illinois would begin to craft memorable Halloween yarns involving pranks and (in later seasons) fantasy. Meet the Conners, the blue-collar family at the heart of Roseanne. The show would become known for its plethora of heart and its Halloween episodes, and as such, there is one in every season except the first. Once you’ve seen them, who can forget the self-dubbed Queen of Halloween, matriarch Roseanne (Roseanne Barr), husband Dan (John Goodman), and the younger Conners’ attempts to one-up each other with pranks, costumes, and fake blood (lots and lots of fake blood)?
Bed snakes, excessive cackling, and Jerry Garcia, oh my! Strap on your Wicked Witch of the Midwest costume, click your remote thrice, and watch all of the zany family’s Halloween adventures on Peacock as you descend through this list of the show’s eight Halloween specials, ranked from worst to best.
8. "Halloween: The Final Chapter" (Season 8, Episode 5)
By Season 8, the show’s writing team was seemingly running out of clever, unforeseen Halloween ideas. Co-written and directed by Barr, “Halloween: The Final Chapter” follows the mold of one of those interminable horror sequels committed to finding new ways to scare its audience… scare them, in Roseanne’s case, with random gag after random gag. The episode finds the Conner clan consulting with a Ouija board, which then sends a message: “THE DEAD” (or “THEDE AD” as Laurie Metcalf's Jackie first reads it). After a pregnant Roseanne asks when her baby will arrive, the word “NOW” appears, and she’s catapulted to a delivery room manned by doctors in Halloween garb (“That’s the problem with HMOs, you can never pick your doctor,” Roseanne groans). What ensues: a flashback sequence, a Jerry Garcia tribute appearance (he had just died), a bizarre psychedelic dance number, and then Roseanne’s baby is shown cradled in her arms. Perhaps a purposeful attempt to jump the shark, much of it feels like lunacy for the sake of lunacy, and the 3-minute flashback sequence certainly is filler. It’s the series’ worst Halloween episode because it plays out like scenes drawn from a hat, ideas that were maybe funny in the writers’ room but don’t translate well to an episode of television. But a young trick-or-treater threatening Roseanne, “I’m gonna sue you so fast you’re gonna need Johnnie Cochran” will never not be funny, so there’s that.
7. "Skeleton in the Closet" (Season 7, Episode 6)
Perhaps a controversial placement, this fan favorite continues the theme of Season 6’s Halloween episode: prank Roseanne. The problem with this one, though, is that the prank in question (convincing Roseanne that Jackie’s husband, Fred, is in fact gay) can be seen from a mile off. It’s not exactly believable that noted trickster Roseanne would buy into such a far-fetched scheme. Additionally, the gay jokes in the episode’s beginning, as Roseanne's boss Leon hits overtly on a rigid Fred, are rather dated, as is the procession of gay hairstylist stereotypes trodded out in the episode’s through-line of Roseanne being certain that her mother is wearing a wig (though Nancy’s “You know what they say about men who complain about gay men… The squeaky wheel wants to get greased” is a perfect joke). Of course, the “outed Fred” storyline nets a hilarious payoff (Fred in bed with Dan), and the scene where David (Johnny Galecki) explains, in PG-fashion, the concept of homosexuality to a nonplussed D.J. manages to be funny and sincere in its acceptance of a then-taboo-for-network-TV topic. But the rest of the episode feels rather limp and dated, making it one of the series’ lesser Halloween entries.
6. "Satan, Darling" (Season 9, Episode 7)
This wackadoo episode is often considered to be the nadir of the show’s Halloween installments. Its position inside the commonly derided Season 9 -- the infamous one where it was all a dream -- doesn’t do it any favors. And the episode’s mise-en-scene is foreign, too. Gone in this episode are the traditional sets of the Conners’ home, and the pastoral feeling of autumn in an Illinois town, in favor of a cold, stuffy New York City mansion. And it isn’t until the halfway mark that the episode even remotely begins to resemble a Halloween episode, with the incorporation of a Rosemary’s Baby parody. But breaking away from the by-now tired interfamily prank battles was a smart move. Satirizing the vacuous lifestyle of socialites -- whom Roseanne mills about with due to her recent $107 million lottery win, the central arc of Season 9 -- and then weaving it all together with a Rosemary’s Baby fever dream coda is pretty daring, even for a show that was now openly pursuing the fantastical (to some people, a violation of its original down-to-earth appeal). What’s important is that, in spite of the (mixed) results, the show swings for the fences instead of bunting. And the show could still write the hell out of a one-liner -- following daughter Darlene’s (Sara Gilbert) incredulity at how large she is given she’s only 8 weeks pregnant, Roseanne replies, “That isn’t normal for 8 years pregnant.” Haw-haw.
5. "Halloween V" (Season 6, Episode 6)
In this perfectly funny episode, the Conner family manage to outmaneuver the heretofore Prank Queen Roseanne for a change. First, there’s the case of Nancy (Sandra Bernhard), one of the co-owners of the Lanford Lunch Box diner along with Roseanne and Jackie. The estranged wife of Dan’s poker buddy Arnie, the vain Nancy thinks Dan doesn’t like her; to her credit, she’s right. Roseanne comes up with the idea for Dan to play a prank on Nancy (“God beat me to it,” Dan casually retorts) so that Nancy will think everyone likes her. Along the way, Dan ups the ante in the forever-ongoing Conner Prank War by staging a robbery at the Lunch Box. What’s funny here is how Roseanne’s penchant for practical jokes is turned against her; initially, she leans into the joke, giving the robber her house key and wedding ring, before deciding that maybe it was an actual robbery… Meanwhile, daughter Darlene and boyfriend David (Johnny Galecki) pull an elaborate prank on Roseanne by making her think David is cheating with a classmate, Sally. This all culminates, in typical Roseanne fashion, with a severed head and fake blood. Though little of this subplot is actually funny (think teen drama ala Beverly Hills, 90210), it plays out better on rewatch because you can appreciate the masterful buildup of their plan. Those crazy kids sure learned from the best. Additional props to this episode for providing a costume idea for Hot Topic couples: Romeo and Juliet after the suicide.
4. "Trick or Treat" (Season 3, Episode 7)
Gender, and the subversion of norms relative to men and women, play a big part in this funny episode. “Trick or Treat” (story credited to Future Titan of Multicam Network Sitcoms Chuck Lorre) begins with Rosanne and Jackie arriving home to Dan and his buddies guyin’ it up during a poker game (“They’re the only animals that think black socks go with Bermuda shorts,” says Roseanne). This duality becomes key to the main storyline, which finds Roseanne’s truck driver costume getting her mistaken for a man at the local watering hole. Roseanne, per her nature, plays into this identity with zeal, and Barr the actress gives a credible performance as a chauvinist beer-drinker (props to the makeup department as well, for that matter). While milling about with a gang of pool players, she fits in by humorously reflecting their soft-branded sexism, as well as by uttering the (supposedly) magic words for Neanderthal men: “Bada-boom, bada-bing!” If there’s a flaw, it’s the episode’s other subplot, which sees Dan coming to terms with son D.J. wearing a (girl) witch costume. In 2021, Dan’s concerns come across as rather dated 90s sitcom fodder, even perhaps a bit sexist. But the episode ultimately makes the case for good, upstanding men in the episode’s ending, when Dan breaks up a scuffle between the male-disguised Roseanne and a man whose pride she wounded, with the line, “He’s my husband.” The gender satire in this storyline has aged like wine, and it has all of the heartfelt elements that made Roseanne such a penetrating show at times.
3. "Trick Me Up, Trick Me Down" (Season 4, Episode 6)
“When will we learn?” Roseanne asks to start another installment of Conner Haunted House Bedlam. Comedy comes from pain, and the shock and horror on neighbor Kathy’s face upon witnessing a gutted Dan lying on the table is a thing of beauty. Penned by future Gilmore Girls creator Amy Sherman-Palladino, “Trick Me Up, Trick Me Down” really captures the fun of the holiday better than any episode except perhaps the series’ first. And it also contains some of the best jokes: D.J.’s cowlicked “Alfalfa-ator” costume, replete with machine gun and Schwarzenegger-esque shades; Roseanne’s overtly obvious stalking of Kathy at the party, concerned she’s going to try to enact revenge for her earlier prank. Ultimately, the episode really shines as a series of memorable setpieces and sequences without much narrative tissue connecting them. But when you have Dan and Roseanne’s delightfully cornball ventriloquist act as Deadgar Bergen and Mortuary Snerd as one said sequence, you can live without it. The episode’s cleverest bit of writing comes with Dan’s narration of his wife’s thought-process as she smartly dissects the obvious bucket-above-door prank he plays on her (he wants her to think Kathy did it, so she can sleep easy). Dan and Roseanne reached a 90s equivalent of couple goals, and moments like these that illustrate their lockstep thinking prove it.
2. "Halloween IV" (Season 5, Episode 7)
Maybe one of the most ubiquitous television tropes is the trodding out of an A Christmas Carol spoof. The Odd Couple did it, Beavis and Butt-Head made a mockery of it, and, did someone say Scrooged? And Roseanne achieves a high watermark of its Halloween lineup with its retelling of the Dickens classic. An unusually despondent Roseanne dreams up three Halloween ghosts -- Past, Present, and Future -- to reacquaint her with the spirit of Halloween. Past shows a young Roseanne learning the ropes of Halloween pranking, including a delightfully cheesy retelling of hers and Dan’s meetcute (at a Halloween dance, of course). Present shows Roseanne what she’s missing at the party: sadness over Roseanne’s absence and also a bit of palpable relief (she’s a wild card, after all). In the funniest segment of all, Ghost of Halloween Future imagines Roseanne as a 50s housewife more concerned with safety than the panache of a good practical joke, and then as an old spinster, presumably due to her lack of Halloween spirit. Cue a Wilhelm Scream movement. Just like how the miserly Ebenezer Scrooge learns the joys of the holiday season, the ghosts’ visit does its job and returns the woman to her normal hallelujah-Halloween self. Even considering the series’ high batting average for high-concept Halloween episodes, “Halloween IV” outdoes itself with its humor and pathos. It’s a contender for one of the best Halloween television specials, period. And it shows how much we need the Queen of Halloween to exploit the holiday for all its worth.
1. "BOO!" (Season 2, Episode 7)
A true classic in the Roseanne catalog, this episode cements the Conners’ wacky fascination with the holiday. And their dedication. Their home -- designed into a haunted house replete with decorations, cauldrons, and tricks involving severed heads under silver domes -- shows the family would be adept at running their own Fear Farm. Unlike future Halloween installments, this one is plot-free and coasts along from one practical joke to the next, upping the ante each time: Dan and Roseanne tell the kids a fake story of an insane asylum escapee; then daughter Darlene has a missing tongue; and finally, the series staple of Dan vociferously squirting blood from a fake injury makes its debut (“This is a sick household,” opines Jackie). The misadventures are so fun that the lack of any real storyline doesn’t make an iota of difference. Perhaps the show’s episode that best nails the gleeful zeal and spirit of Halloween, Season 2’s “Boo!” proves that sometimes first is best, and is essential viewing for fans of pranks and (family-friendly) gore alike. It’s also great to mine ideas for a DIY haunted house yourself; the set designers really deserve kudos for that one.