Arguably the most successful period in the history of World Wrestling Entertainment, the Attitude Era saw WWE bounce back from the creative slump of the New Generation Era by pivoting to being less kid-friendly. As such, WWE’s on-screen product grew more edgy, with not only more violent in-ring content, but also provocative sexual themes and crude humor.
RELATED: WWE: 10 Feuds That Defined The Attitude Era
While there were loads of memorable storylines during this period like Stone Cold Steve Austin’s rivalries with The Rock and WWE boss Vince McMahon himself, there were also some feuds that were downright weird. Let’s take a look at 10 of these strange angles, which resulted in some of the Attitude Era’s most infamous moments.
10 Dean Malenko vs. Lita
After jumping ship from WCW, “The Iceman” Dean Malenko experienced a lackluster run in WWE, albeit one that included a 322-day reign with the Light Heavyweight Championship before he retired in 2001. During that WWE run, Malenko was given a “ladies man” gimmick that saw him pursue an uninterested Lita. This resulted in Malenko putting his title on the line against Lita in a match, with the added stipulation that she had to go on a date with him if she lost. This weird feud was arguably Malenko’s biggest storyline, believe it or not.
9 Hawk vs. Droz
Real-life circumstances being fair game for pro wrestling storylines was hardly anything new even back during the Attitude Era, but WWE may have crossed a line with the Legion of Doom’s angle with their new addition, Droz. Behind the scenes, Hawk was dealing with alcoholism and other problems, which soon became a kayfabe liability. Before long, it was revealed that Droz was actually enabling Hawk’s problem, resulting in questionable segments like Hawk taking a dive off of the Titantron.
8 Val Venis vs. Kai En Tai
Defying heel/babyface dynamics, any given feud Val Venis would invariably involve him videotaping himself sleeping with another wrestler’s female companion. In 1998, he ran afoul of Japanese heel faction Kai En Tai, doing the same with manager Yamaguchi-San’s wife, Mrs. Yamaguchi. Seeking retribution, Yamaguchi-San vowed to “choppy choppy” the “pee-pee” of WWE’s resident pornstar.
RELATED: 10 Things WWE Fans Should Know About The Japanese Stable Kai En Tai
What made the feud truly weird was the conclusion. Eventually Kai En Tai captured Venis and attempted to dismember him, only to be rescued at the last moment by John Wayne Bobbitt, who made headlines in 1993 for suffering the same.
7 Debra vs. Sable
While Debra initially joined WWE as Jeff Jarrett’s valet, she eventually branched out into competition herself, feuding with the promotion’s top female talent at the time in Sable. At the time, Sable was Women’s Champion, and their Evening Gown Match for the belt on the 5/10/1999 episode of Raw ended up making this one of the stranger feuds of the women’s division. Normally, the winner of the bout was the one who ripped off her opponent’s dress, but WWE authority figure Shawn Michaels decided that Debra, who technically lost the match, was the winner and new Women’s Champion based on the fact that she got more naked than Sable.
6 Goldust vs. Val Venis
While the former Dustin Rhodes certainly made a splash in WWE as the provocative Goldust, by 1998 he had shed the gimmick, going the opposite direction as a conservative, morally strict character under his real name of Dustin Runnels. During this storyline, Val Venis, — as expected established — filmed an adult movie with Dustin’s estranged wife, Terri. This, of course, drove Runnels mad, and he reverted to the Goldust character, taking on Venis at several pay-per-views. To make matters weirder, Goldust/Dustin was technically the bad guy in this feud.
5 Crash Holly vs. The Mean Street Posse
Established in 1998, the WWE Hardcore Championship had a significant change in direction in February 2000 when new champion Crash Holly committed to defending 24 hours a day, regardless of whether he was in a wrestling ring. As a result, the Hardcore Title became WWE’s wackiest championship as Holly feuded with Shane McMahon’s hapless hangers-on, the Mean Street Posse. Pete Gas, Rodney, and Joey Abs were determined to capture the belt, and challenged Holly in all kinds of strange places, including a circus and an airport.
4 Goldust vs. Bluedust
Given Goldust’s nickname of “The Bizarre One,” it’s only natural that he’d be the focus of at least two of the Attitude Era’s weirdest feuds. In 1999, Goldy got into a feud with former ECW cult hero The Blue Meanie, with Meanie doing what he does best — adopting a parody gimmick — to become “Bluedust.”
RELATED: 10 Things Wrestling Fans Should Know About WWE & ECW Wrestler The Blue Meanie
After Goldust defeated Bluedust at St. Valentines Day Massacre, things only got weirder — Blue Meanie shed the Bluedust gimmick, but became subservient to Goldust, becoming part of his entourage.
3 Cactus Jack & Chainsaw Charlie vs. The New Age Outlaws
In the mid-’90s, Terry Funk and Cactus Jack put on some epic deathmatches in Japan, but in the Attitude Era the two ended up becoming tag team partners in WWE. Things were already weird from the get-go, as Funk didn’t wrestle as Terry Funk but rather as the erratic, chainsaw-wielding Chainsaw Charlie, getting into a feud with Tag Team Champions The New Age Outlaws. Things came to a head at WrestleMania 14 as Charlie and Jack dethroned Road Dogg and Billy Gunn in a Dumpster Match, a hardcore match where a wrestler must be thrown into a dumpster.
2 Shane McMahon vs. Test
In mid-1999, Stephanie McMahon entered a romance angle with Test, much to the chagrin of Steph’s overprotective brother, Shane McMahon. This, of course, resulted in a feud between the two men, culminating in SummerSlam 1999 as the two squared off in a “Love Her Or Leave Her” Match, a street fight that determined Stephanie’s romantic future and included interference from the aforementioned Mean Street Posse. It actually proved to be a surprisingly fun rivalry, but it’s undeniable that Shane fighting Test over his own sister was kind of weird.
1 Big Boss Man vs. Al Snow
One of the biggest gimmick match disasters of the Attitude Era was arguably the Big Boss Man vs. Al Snow Kennel From Hell Match, a cage match with live dogs that isn’t as exciting, dangerous, or fun as it sounds. But the story of the feud leading to that bout is just as weird. At the time, Al Snow had a dog named Pepper that he adored, so Boss Man decided not only to kill Pepper, but also cooked the dog and fed it to Snow without him knowing.
