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Celebrating the Many “Roseanne” Halloween Specials

Welcome to… THE TUNNEL OF TERROR.

Few television shows in history were more ahead of their time than Roseanne, which premiered on ABC back in 1988. Never afraid to tackle hot button issues – many of which are as “hot button” today as they were back then – the series was quite unlike anything else on the small screen at the time, documenting the day-to-day lives of a fictional family that probably wasn’t all that different from your own. The Conners looked like us, they acted like us, and they faced the same struggles we all do, so it was only natural that they quickly became one of the most beloved television families of all time.

And like us, they LOVED Halloween.

The show’s creator, Roseanne Barr, is herself a big time fan of Halloween, and if it was up to her, the very first season of Roseanne would have explored the Conner family’s love of the holiday; it wasn’t, however, until the second season that Halloween episodes became an annual tradition for the show. To make a short story even shorter, ABC just wasn’t into the idea of celebrating Halloween, fearing that some viewers would be turned off by the satanic implications of the holiday. Of course, Roseanne went on to become a show that defied any and all political correctness, and by the time Season 2 came around, the network caved and allowed Barr to do what she wanted to do one year prior.

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Premiering on Halloween night of 1989, ‘BOO!’ was the very first Halloween episode of Roseanne, and many viewers to this day consider it to be the best Halloween special ever made. The episode, which perfectly captured small town Halloween, saw the Conner family embracing the holiday to the fullest extent of the law, notably turning their modest home into a wonderfully over-the-top haunted attraction for trick or treaters. The episode also established Dan and Roseanne’s Halloween tradition of attempting to out-prank one another, which carried over into several of the subsequent episodes; eight in total, from Season 2 through 9.

Following all the rules of Halloween to a tee, the Conner family of course also dressed up each time the calendar flipped over to October 31st, and their costumes were always one of the most fun aspects of the annual episodes – sometimes, they were even a bit controversial. In 1990’s ‘Trick or Treat,’ young son DJ’s costume choice saw the show, in typical Roseanne fashion, bravely confronting something no other show would have dared at the time. DJ decided to dress up as a witch for Halloween, which concerned Dan; “Boys shouldn’t dress up like girls,” Dan says to Roseanne, worried about the implications of the costume.

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The Halloween costumes were all around a highlight of ‘Trick or Treat,’ the show stepping up the game big time from the previous year. Dan dressed as the Three Stooges, with dummy heads on each side of his own; Becky was a mangled prom queen (Prom Night 2, anyone?); Darlene, in one of the show’s most GIFable moments, had a chest-bursting creature underneath her sweatshirt; and Roseanne went as a lumberjack man for a hilarious and insightful trip to the bar. The rest of the family that year attended a local haunted attraction rather than putting on their own, presumably because Lanford cracked down on that sort of thing.

The prank wars continued in ‘Trick Me Up, Trick Me Down,’ which kicked off with a neighbor being fooled into believing that Roseanne had brutally butchered Dan; the Conner family patriarch’s flair for DIY practical effects was often quite impressive. A bit older by the time the 1991 Halloween season came around, Darlene and Becky had no interest dressing up that year, but Dan and Roseanne donned their most extravagant costume ever for a local Halloween party: they played Deadgar Bergen and Mortuary Snerd, a ventriloquist and his dummy. The episode also featured a young George Clooney dressed as a moose, making a return to the series as Jackie’s ex-boyfriend Booker.

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But Halloween wasn’t always fun and games for the Conners.

Appropriately titled ‘Halloween 4,’ Roseanne’s fourth Halloween special saw Roseanne struggling to get into the Halloween spirit (we’ve all been there, am I right?), and the cure came in the form of a dreamlike visit from the so-called ghosts of Halloween past; even various family pranks, which included Dan grinding up his hand in the garbage disposal, failed to do the trick. Roseanne visited Halloween experiences from her past, present and future, ultimately leading her to reclaim her throne as the Queen of Halloween by dressing up as the Statue of Liberty and setting off the sprinklers at the Lanford Lodge’s annual party.

‘Halloween 4’ featured some of the show’s best costumes, including Dan and Jackie as a decapitated Marie Antoinette and her severed head; Darlene as Tippi Hedren from The Birds; and DJ as Hannibal Lecter.

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The 1993 episode, ‘Halloween 5,’ mostly took place at Roseanne and Jackie’s diner The Lanford Lunchbox, where the pranks were taken to the next level. Dan hired work a buddy to faux rob the diner at gunpoint, and shortly thereafter, the blood flew when a door slammed on Dan’s nose and broke it; unfortunately for him, that was not part of his prank. Things got even gorier when Darlene literally ripped the head off of a girl her boyfriend was apparently hooking up with, though it was of course an elaborate prank on Roseanne. Like mother, like daughter.

‘Skeleton In the Closet,’ the seventh season’s Halloween episode, centered on a party held at the Lunchbox, hosted by gay co-owner Leon Carp (Martin Mull). Homosexuality was a big topic of discussion in the episode, and one of the main storylines saw Jackie suspecting that her boyfriend was gay; it ended with him being “caught” in bed with Dan, which was another good old fashioned Halloween prank. The party that year was, needless to say, a little bit different than the ones we had come to expect from the show, with Roseanne dressed as Prince, Dan as a cowboy, and Jackie as Batman sidekick Robin. A running gag about Roseanne’s mother wearing a wig culminated in an Emmy-nominated sequence that saw every character pulling off their hair to reveal bald domes underneath. Roseanne one-upped them, blowing up the family home.

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Common in the world of horror, ‘Halloween: The Final Chapter’ actually was not, but the second-to-last Halloween special was quite a bit different than all the others. Roseanne, who was pregnant at the time, goes into labor while playing with a Ouija Board on Halloween, and the drugs given to her at the hospital send her on a psychedelic trip that ends with the birth of the newest family member: Jerry Garcia Conner. The episode’s highlight is a montage of memorable clips from past Roseanne Halloween specials, which mostly reminded how good the show’s Halloween episodes used to be.

The true final chapter of the Roseanne Halloween specials was Season 9’s ‘Satan, Darling,’ which aired in October of 1996. By that point, Dan and Roseanne had struck it rich in the lottery, completely changing the direction of the show – in the eyes of many, including myself, for the worse. The final Halloween episode saw Roseanne and Jackie attending a fancy party with New York socialites, the second half playing out like a tribute to Rosemary’s Baby – Roseanne imagines that Darlene is pregnant with the spawn of Satan. The less said about this one, the better.

They may have gone on long enough to eventually jump the shark, but the Roseanne Halloween episodes remain a high watermark for television Halloween specials, paving the way for all subsequent shows to celebrate a holiday that was once completely absent from the small screen. There are few shows nowadays that don’t acknowledge Halloween in October, and Roseanne did it both first and, if you’re asking me, best. Particularly in the early seasons, the Conners’ celebrations showed that it was okay to get crazy, let loose, and have a whole lot of spooky fun on Halloween, and to this day, Halloween just doesn’t feel like Halloween until I’ve revisited their annual tricks, treats, and hijinks.

On Halloween, we should all aspire to be more like the Conners.

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