10 Weirdest Moments Of Stephanie McMahon's Career

Stephanie McMahon has been on WWE television for well over 20 years now. The post-college life of Stephanie led to her joining the family business of being on national television with millions of viewers. Stephanie took to wrestling for success in both the on-screen and backstage elements of the job as a McMahon.

RELATED: Every Version Of Stephanie McMahon, Ranked From Worst To Best

Fans have loved to hate Stephanie as a heel character throughout the years. WWE has booked her with different characters and angles to utilize her on television. There were some bizarre instances to play out with fans confused about what WWE was going for or how it was executed. Stephanie tried to make the weirder moments of her career work to mixed results.

10 Bullying Big Show

WWE placed Big Show in a ridiculous storyline that revolved around him losing his money in investments and needing help to provide for his family. Stephanie McMahon and Triple H used that to force Big Show into doing their bidding.

RELATED: 5 Times Stephanie McMahon Bullied A Male Talent (& 5 Times She Did It To A Female)

Actions like attacking Daniel Bryan or punching Dusty Rhodes hurt Big Show but he kept it going to hold his job for weeks. Stephanie berated Big Show and even slapped him in the face numerous times when he went against her before a firing.

9 Drugging Shawn Michaels For Vince

The first pregnancy of Stephanie McMahon did not completely remove her from WWE. There was a weird appearance of Stephanie showing up backstage to have a conversation with Shawn Michaels before he faced Shane.

Michaels trusted Stephanie enough to get her water at her request while she slipped a substance into his water. The action led to Michaels passing out in his match against Shane and joining Vince’s KMA Club for an embarrassing moment.

8 Kissing Eric Bischoff

The initial WWE brand split featured strong General Managers of Eric Bischoff for Raw and Stephanie McMahon for Smackdown. Bischoff and Stephanie had a rivalry that resulted in them invading each other’s shows, stealing talents and looking to get any advantage in the war.

A bizarre segment during a Halloween themed episode of Smackdown featured Bischoff appearing under a Vince McMahon mask to approach Stephanie. Bischoff unmasked and kissed Stephanie, but the stranger part was her kissing him back.

7 Teaming With Zach Gowen Vs Big Show

One of the most unlikely matches in Smackdown history featured Stephanie McMahon teaming with one-legged wrestler Zach Gowen against Big Show. Stephanie was the Smackdown General Manager, but Vince had power and wanted to block him from getting a contract.

Gowen and Stephanie had to win for him to receive the contract and they pulled off the upset. Brock Lesnar and Kurt Angle interfering to get the better of Vince and Big Show allowed Stephanie and Gowen to score an unexpected victory.

6 Vince Kissing Her Lips In Backstage Segments

WWE wanted to make the McMahon-Helmsley Regime the top heels in wrestling. Triple H and Stephanie McMahon were doing a great job to get strong heel heat, but Vince turning on The Rock at WrestleMania 2000 to join them added more hatred for the act.

One of the most bizarre things from this chapter of Stephanie’s career featured Vince kissing her on the lips. WWE was hoping it would get them more heat, but it just came off strange more than anything else.

5 "I Quit" Match With Vince

The Smackdown General Manager run of Stephanie McMahon ended due to a stipulation for her feud with Vince McMahon. WWE usually had Vince and Stephanie closely bonded together in storyline, but this was a rare feud between the two.

RELATED: 10 Backstage Stories About Stephanie McMahon We Can't Believe

Vince was trying to have another run as a ruthless heel and Stephanie stood up to him as the GM. An “I Quit” match between the two featured the bizarre visual of Vince choking Stephanie out with a lead pipe. Stephanie losing the match via Linda quitting on her behalf ended the GM run and Paul Heyman replaced her.

4 Dancing With New Day

Stephanie McMahon was viewed as an intimidating authority figure on WWE television over the past decade. There were some rare moments with Stephanie letting loose and having fun instead of always being serious.

Triple H and Stephanie both acted out of character during an interaction with New Day. The trio of Kofi Kingston, Big E and Xavier Woods convinced the hated couple of The Authority to dance with them for a funny moment.

3 Daring John Cena To Give A Little Tap

The face run of Stephanie McMahon as Smackdown General Manager was a tough sell for fans at first. Stephanie eventually won them over by interacting with face characters to prove she had changed from her hated character.

One unique way to get crowd support featured Stephanie sharing an “intimate” moment with John Cena during his time with the rapping gimmick. Stephanie followed up a Cena rap by asking him to smack her backside like he said in his rap even though it made little sense in the big picture

2 Getting Pied By A Planet Of The Apes Ape

The rivalry between Chris Jericho and Stephanie McMahon featured some of the most memorable moments of her career. Jericho became the thorn in Stephanie’s side when insulting her with brutal and vulgar insults to the crowd’s delight.

An odd moment featured WWE trying to do a tie-in with then-popular movie Planet of the Apes. Jericho orchestrated for someone in an ape costume to enter the ring as a blind date for Stephanie, who pied her in the face for the humiliation.

1 Dream Sequence On Raw

WWE ran one of the most bizarre segments in WWE history that featured a dream sequence. Vince McMahon was in a coma with actor and then-WWE writer Freddie Prinze Jr. as his doctor as he got out of it.

There were some jokes about Vince spending millions on Linda’s failed political campaign to add to the humor. The big reveal ended with Stephanie waking up in bed with Triple H at her side. Vince still being in a coma and her joy about it ended it as a comedic segment without an intended payoff.

NEXT: 10 Things You Didn't Know About Triple H & Stephanie McMahon's Relationship