Stephanie McMahon is one of the most influential figures in WWE, both off and on the screen. She has been active since 1998, making her a veteran with over two decades of experience in the industry.
The Billion Dollar Princess has played the role of a wicked boss for a very long time, and she has used her power to manipulate her rivals often. From the Attitude Era to today, Stephanie has been part of many interesting storylines, with a majority of them as a heel. Being on the TV for so long, it is inevitable to not face embarrassing moments in her lengthy career.
10 Getting MANhandled - RAW, February 4, 2019
Even though Becky Lynch won the Women's Royal Rumble match, she was denied the opportunity to particulate in the main event of WrestleMania 35 due to a kayfabe leg injury. Stephanie told Becky that she would have to see WWE doctors before she can clear her for the Show of Shows.
Becky Lynch wasn't willing to see the doctor, and she immediately ambushed Stephanie. The Man was so fired up that the security had to come out and save Stephanie McMahon.
9 Ronda Rousey Getting The Upper Hand At WrestleMania 31
Arguably one of the most memorable WrestleMania moments was at WrestleMania 31 where Triple H and Stephanie McMahon were humiliated by Ronda Rousey and The Rock.
Stephanie told Ronda to leave the ring. After exchanging heated words, things soon turned physical. While The Rock attacked Triple H, Ronda blocked Stephanie's slap and teased an armbar. The power couple had no choice but to leave their own ring.
8 The Spear At WrestleMania 32
Triple H and Roman Reigns crossed paths for the WWE World Championship at the Grandest Stage of Them All in 2016. As always, Stephanie McMahon was by her husband's side at ringside.
In the middle of the match, Stephanie was arguing with the referee. While doing so, Reigns tried to spear Triple H but instead, hit Stephanie McMahon, who was laying there in pain after getting broken in half.
7 Chris Jericho Pies Stephanie - RAW, August 6, 2001
Chris Jericho's career got more interesting in the Attitude Era by embarrassing Stephanie McMahon regularly. He would often make inappropriate jokes on Stephanie, to which she hardly had any befitting replies.
One such instance was when Y2J implied that Stephanie had slept around, so he decided to set her up with members of Planet of The Apes. Jericho introduced Stephanie to the apes, and he threw pie on Stephanie's face.
6 The Rock and Chris Jericho Insult Stephanie - RAW, August 13, 2001
Perhaps one of the greatest RAW segments of any era took place when The Rock and Chris Jericho teamed up to confront Stephanie McMahon, Rhyno, and Booker T. After The Rock was done insulting Booker T, he turned his attention to Stephanie, and Jericho also joined the party.
The Rock did a rhyme throwing shade at Stephanie. Meanwhile, Stephanie was so embarrassed that she didn't have anything to say other than 'Shut up'.
5 Thrown In A Pudding By Vickie Guerrero - RAW, June 23, 2014
Stephanie McMahon tried humiliating Vickie Guerrero by arranging a pudding match on RAW. Stephanie got help from Layla, Rosa Mendes, and Alicia Fox, but Vickie managed to throw all of them in the pool of pudding. Seeing a perfect opening, Stephanie pushed Vickie into the pool and announced that she was fired.
After being fired, Vickie had nothing to lose. Therefore, she grabbed Stephanie and threw the Billion Dollar Princess in the pool of pudding, making it one of the most embarrassing moments in Stephanie's career.
4 Triple H Crashed Stephanie McMahon's Wedding With Test - RAW, November 29, 1999
Triple H and Stephanie McMahon might have gotten married in real life, but her real-life husband once crashed her reel wedding on RAW. When Stephanie was about to exchange rings with Test, The Game spoiled the party by revealing that she had already married Triple H.
It was shown in a video clip that Triple H and Stephanie tied the knot in a drive-through ceremony in Las Vegas when Stephanie was out cold.
3 AJ Lee's Jab About Stephanie's Marriage - RAW, June 17, 2013
After AJ Lee won the Divas Championship at Payback 2013, Stephanie McMahon confronted AJ Lee in the ring. She ordered AJ to act like a proper champion, to which the Divas Champion had a harsh reply, as it certainly embarrassed the Billion Dollar Princess.
AJ told her that to be a proper champion like Stephanie was talking about, she might have to stop dating top Superstars and instead, she should marry one, taking a subtle jab at Stephanie's marriage.
2 Getting Rock Bottomed (WrestleMania 2000)
The Rock faced Triple H, Mick Foley, Big Show, and Triple H in a Fatal 4 Way match in the main event of WrestleMania 2000. Vince McMahon turned on The Great One, and it was one of the reasons The Rock failed to capture the WWE Championship.
Following the match, The Rock left, but he eventually came back to the ring and attacked Vince McMahon. Then Stephanie slapped The Rock, and the latter responded by delivering her a Rock Bottom as well as a People's Elbow.
1 Chris Jericho's Insult On Stephanie's Birthday
Another popular Chris Jericho insult to Stephanie McMahon was on her birthday. It was a backstage segment when Y2J came face to face with Stephanie.
Chris Jericho asked Stephanie her age, saying she was probably going to be 37 or 38 years old. A surprised Stephanie countered him, saying it was just her 25th birthday. But Jericho mortified her once again saying that he asked about her age, not the number of men she's been with in the previous week.