The Best and Worst WWE Halloween Moments Ever

BEST: John Cena Dresses as Vanilla Ice — SmackDown, 2002

John Cena showed up to a Halloween party on the Oct. 31, 2002 episode of SmackDown dressed as Vanilla Ice. Stephanie McMahon heard Cena could freestyle and asked him to prove it.

What looked like a comedy segment helped WWE discover the personality that had been missing from Cena’s original presentation. The freestyle led to the Doctor of Thuganomics character and eventually helped turn Cena into the biggest star of his generation.

There have been better Halloween matches, but nothing on this list had a bigger impact. A Vanilla Ice costume helped change John Cena’s career.

BEST: Rey Mysterio vs. Eddie Guerrero — Halloween Havoc 1997

If we’re talking strictly about the best Halloween match, this is No. 1.

Rey Mysterio challenged Eddie Guerrero for the WCW Cruiserweight Championship with his mask also on the line. Mysterio, wearing gear inspired by The Phantom, eventually caught Guerrero with a top-rope hurricanrana to win the title and keep his mask.

I was a baby when this happened, so I don’t have some childhood memory attached to it. Watching it nearly 30 years later, though, it’s easy to understand why it’s still considered one of the greatest matches in WCW history.

BEST: Goldberg vs. Diamond Dallas Page — Halloween Havoc 1998

Goldberg entered Halloween Havoc 1998 as undefeated WCW World Heavyweight Champion, while Diamond Dallas Page had become one of the company’s biggest stars.

DDP hit the Diamond Cutter and came remarkably close to ending Goldberg’s streak before Goldberg recovered and won with the Jackhammer. WWE later ranked it among the 20 greatest matches in WCW history.

Unfortunately, WCW made a massive mistake that prevented some paying viewers from seeing the finish. More on that shortly.

WORST: The Giant Falls Off a Roof — Halloween Havoc 1995

Before Hulk Hogan defended the WCW Championship against The Giant, the two competed in a Monster Truck Sumo Challenge on the roof of Detroit’s Cobo Hall.

Afterward, Hogan and The Giant fought near the edge of the roof, and The Giant fell off the building. Somehow, he returned later that night and wrestled Hogan in the main event.

The Yeti, who looked much more like a giant mummy, then appeared and helped attack Hogan. The whole thing has aged past bad and become hilarious.

WORST: Hulk Hogan vs. The Ultimate Warrior — Halloween Havoc 1998

Eight years after Hulk Hogan and The Ultimate Warrior headlined WrestleMania VI, WCW decided to run it back.

The rematch was slow, overbooked and featured an infamous fireball spot that went wrong when Hogan struggled to ignite the flash paper. Hogan eventually won with help from Horace Hogan.

WCW tried to recreate one of WWE’s most famous matches and instead produced one of Halloween Havoc’s most infamous.

WORST: WCW’s Halloween Havoc PPV Ends Before the Main Event Does

This has to be No. 1.

Halloween Havoc 1998 ran beyond its scheduled pay-per-view window, causing some providers to cut the broadcast while Goldberg and DDP were still wrestling in the main event.

Fans paid to see Goldberg defend his title and undefeated streak, only for their screens to go black before the finish. WCW aired the entire match for free on Monday Nitro the following night.

Making it worse, Hogan and Warrior had wrestled for more than 14 minutes earlier on the card. WCW found time for one of its most infamous matches and then ran out of time during one of its best.

That might be the perfect summary of Halloween Havoc. At its best, WCW gave us Mysterio vs. Guerrero. At its worst, a man fell off a roof and came back to wrestle later that night.

Wrestling at Halloween should be a little ridiculous. WCW occasionally took that assignment too seriously.