Welcome to 2026's 31 Days of Heistoween, a daily dose of spooky icons, spine-tingling oddities, and — most harrowing of all — memes. Check back every day from now through October 31 for each daily entry!
Professional wrestling has always had a soft spot for the supernatural — from witch doctor Papa Shango cursing his opponents, the Undertaker evolving from undead mortician to full-on necromancer, Kane having been resurrected from the flames, otherworldly cult leader Bray Wyatt turning nightmares into television, and Finn Bálor unleashing his own demonic persona. More recently, Danhausen has brought his peculiar brand of horror-comedy to WWE, proving there's still room for a little mischief in the squared circle. Wrestling loves a good scare, and with Halloween approaching, Pop Heist's Heistoween is the perfect excuse to revisit some of its strangest moments.
We've already explored WWE's casket matches earlier this month, so let's turn our attention to a different kind of wrestling horror: a murderous doll, a family feud, and a movie promotion that went completely off the rails.
On October 12, 1998, WCW Monday Nitro was building toward the annual Halloween Havoc pay-per-view, where Rick Steiner was preparing to settle a score with his brother Scott, who had recently joined up with the New World Order (NWO). Then Chucky — yes, the doll — showed up, started running his mouth, and made himself part of the problem.
A mysterious stalker was taunting Rick, giving fans a mystery that might be revealed at Halloween Havoc, but as this was an all-out war for TV supremacy at the time between WCW and WWF, everything was pretty much a free for all over at Turnerland. Chucky was there to promote Bride of Chucky, which hit theaters on October 16, later that week and a week before Halloween Havoc. The film introduced Jennifer Tilly as Tiffany, Chucky's murderous partner, and started to embrace the franchise's mix of slasher horror and dark comedy.
Chucky warned Rick Steiner to stay out of his brother Scott's business, before threatening to twist Rick's head off and leave the scraps for the dogs. Rick, predictably, wasn't impressed. The Dog-Faced Gremlin barked back and challenged the pint-sized menace to come down to the ring and say it to his face.
Even without the campy crossover, Rick Steiner's road to Halloween Havoc was already a mess.
The Steiner family feud was heading toward a showdown at Halloween Havoc on October 25, 1998, but WCW had another wrinkle in store: Buff Bagwell, Scott's former ally, claimed he wanted to help Rick. Bagwell offered to watch Rick's back, and Rick reluctantly accepted as it was a sort of reconciliation that practically begged for a betrayal, especially with Scott lurking in the wings.
At Halloween Havoc, Rick and Bagwell challenged The Giant and Scott Steiner for the WCW World Tag Team Championship. Scott was filling in for Scott Hall, who held the titles with The Giant, but also had a match later on with former tag team partner, and Wolfpac founder, Kevin Nash. The match was chaotic, and Bagwell eventually turned on Rick and walked out. Rick still managed to win the titles, pinning The Giant after an accidental collision between the champions gave him an opening.
Rick then got his singles match with his brother, as promised. He quickly won that fight, too, surviving interference from Bagwell and Stevie Ray to finally get one over on his brother. It should have been a satisfying end to a long-running family feud.
Naturally, WCW had other plans.
On the following night's Nitro, Rick chose Kenny Kaos from the tag team known as Live Wire as his new tag team partner after Bagwell's betrayal. When Kaos was subsequently injured, Rick came up with an entirely different solution: on November 9, he named Judy Bagwell–Buff's mother–as his new championship partner. It was a psychological ploy aimed squarely at getting under Buff's skin, and it was every bit as absurd as it sounds.
Imagine being Buff Bagwell. You betray Rick Steiner, only for him to win the titles anyway, replace you with Kenny Kaos, and then decide that your mother is the ideal person to help him get revenge. Wrestling family therapy has rarely been this complicated.
With the Steiner family feud heating up and Halloween Havoc around the corner, Chucky's appearance on Nitro offered a perfect blend of wrestling promotion and horror-comedy, even though it didn't quite deliver. The possessed doll mocked Rick, backed Scott, and behaved as if he had a personal stake in the family drama. It was a movie tie-in, sure, but it also fit the wonderfully unpredictable atmosphere of late-1990s WCW. Afterall, this was the company that just a few years earlier had RoboCop team with their franchise player, Sting.
WCW gave Chucky a platform, and in turn, the doll gave Rick Steiner a hard time, and audiences got a crossover that could have only made sense (kind of?) in professional wrestling. The segment never led to an actual match between Rick and the doll, which is probably for the best. Rick was busy dealing with Scott, Bagwell, and eventually Judy Bagwell's unexpected tag-team career, he didn't need to add a plastic psychopath to the list.
Still, it's fun to imagine the alternate timeline. Chucky could have been in Rick's corner at World War 3. Maybe he'd have tried to stab Scott with a miniature switchblade. Perhaps Judy Bagwell would have chased him out of the arena with a handbag.
WCW never gave us that match, so we'll just have to live with the mystery.
Chucky had unfinished business with WWE, too
Chucky's wrestling career didn't end in 1998. In October 2021, the killer doll returned to the Halloween Havoc orbit when WWE brought him into NXT to promote his new television series, which aired on USA Network and Syfy. WWE was also promoting its programming through Peacock in the United States, giving the whole arrangement a neat little bit of haunted synergy: a wrestling show, a horror franchise, and a streaming platform all helping each other get eyeballs on one another.
Chucky was back to stir up his own style of Halloween havoc, more than two decades after needling Rick Steiner on WCW television. Apparently, the doll had decided that wrestling was a perfectly good place to advertise his latest murder spree. Danhausen may have WWE's horror-comedy corner these days, but Chucky was an early example of how easily a wrestling promotion could make room for a horror icon with something to sell.
Maybe if Chucky ever comes back to WWE, perhaps someone should warn Danhausen to keep an eye on his cherished teeth collection.
Come knock on our door tomorrow for even more 31 Days of Heistoween treats.
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