5 Naughtiest WWE Superstars Ever

Publish date: 2024-06-17

WWE is the undisputed leader of sports entertainment. The promotion has given fans many unforgettable moments for as long as it’s been around. It has also created some of incredibly popular babyfaces and heels (aka good and bad guys) in the business.

While there are a lot of bad guys that have caused troubles for your favorites, these five men may just be on the top of the naughty list. Let’s take a look at the five naughtiest WWE Superstars to ever step inside a ring:

Brock Lesnar shoved a former WWE superstar down a flight of stairs

Brock Lesnar is one of the most accomplished superstars in the history of this business. The former NCAA Heavyweight Champion was picked right from the University of Minnesota and brought into the business. He had arguably the most successful rookie career, winning the WWE Championship four months into his main roster debut as well as headlining multiple WrestleMania events.

Lesnar may be a fan favorite today, but he’s done some very questionable things in the past. The Beast Incarnate epitomized the Ruthless Aggression Era. During the lead-up to Unforgiven 2002, Lesnar placed his hand on a pregnant Sara Callaway’s belly and called life a b***h. For those unaware, Sara was The Undertaker’s wife at the time.

He also destroyed a handicapped Zack Gowen in front of his mother (the original pitch was way worse). Of course, that was all part of storyline but that didn’t stop it from being an uncomfortable watch.

Kane did some demonic things

I’m probably not the only one who used to be terrified of Kane during the Attitude Era. The man was truly a freak of nature. Also, his mask and long hair made him extremely intimidating. Then he dropped his mask and proceeded to do some of the most heinous acts on WWE television.

Here are just some of the despicable acts Kane did in 2003 alone. He set Jim Ross on fire, tombstoned Linda McMahon, and electrocuted Shane McMahon’s testicles to stop him from procreating with his wife.

The Devil’s Favorite Demon described his tales of torture in an anger management session that also involved former WWE star Daniel Bryan (aka Bryan Danielson). The good thing is that Kane is one of the nicest guys in the industry despite being a total psychopath on screen.

Big Boss Man ruined a funeral

Few would’ve predicted the utter chaos the Big Boss Man character caused during the Attitude Era. The real-life Ray Taylor was a fan favorite during the Golden Era. He took a darker turn during the Monday Night Wars.

Boss Man made viewers uncomfortable when he hijacked Big Show’s dad’s funeral. He attached the coffin to his cop car and dragged it all the way to the road. If you thought that was downright despicable, wait until you see this great Wrestling Bios’ revisit of the storyline behind the awful Kennel from Hell Match.

Triple H even got fans to cheer for Vince McMahon

Of all the nicknames he’s got, the Cerebral Assassin fits him the most. Triple H, at one point, was such a heel that he made fans cheer for Vince McMahon. After turning solo in late 1998, Triple H started to become more vicious and violent in his quest for the gold.

He made the McMahon’s family life miserable in 1999. The Game started things by marrying a heavily drugged Stephanie McMahon in a car. She’d later reveal that as a plot against her father. He masterminded the car attack that cost Steve Austin a year of his career.

He assaulted Lita during the 2-Man Power Trip Storyline with Austin in 2001. Hunter turned on his best friend Shawn Michaels just a few weeks after he returned from his four-year absence. But the worst of them all: the Katie Wick storyline. That could’ve been avoided.

Mr. McMahon character was outrageous on WWE television

We’re down to the final man on the naughty list. He is the man who signed off on the aforementioned storyline and segments. It’s none other than Vincent Kennedy McMahon or Mr. McMahon on television.

The former owner of WWE is arguably the most hated personality to ever step foot inside the squared circle. McMahon’s character work as self-centered, power hungry, perverse, and egotistical Mr. McMahon fully captured the zeitgeist of the Attitude Era.

It is impossible to list every single one of the heinous acts the boss did on screen. Some of the most popular (and controversial) moments from Vince’s WWE career are: doubling down on the Montreal Screwjob, using his daughter Stephanie to get to Austin, romancing Trish Stratus in front of his wife Linda, mocking Shawn Michaels’ faith, and using racial slur.