Stephanie McMahon has now been involved with WWE in an official capacity for about 23 years now. WWE added Stephanie to television in 1999 having storylines involving The Undertaker, Test and her family. Various on-screen roles and backstage roles had Stephanie evolving throughout the years to her powerful position today.

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The polarizing reputation of Stephanie has seen many positives and negatives associated with her name. Stephanie has also found her way into the most cringe-worthy segments that everyone wants to forget. Quite a few moments made fans feel uneasy watching her. The following overlooked moments from her career provided cringe from Stephanie.

10 Vince Kissing Her In Backstage Segments

The WrestleMania 2000 heel turn of Vince McMahon saw him uniting with Stephanie McMahon and Triple H to become an even more powerful faction. Vince’s love of Stephanie as his favorite child became part of their characters here.

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One odd aspect of the dynamic was Vince kissing Stephanie on the lips multiple times in backstage segments. It was done to gain heat, but everyone cringed in between booing. WWE foolishly booked this for about a month before the lip kissing ended.

9 Telling Freddie Blassie He's Going To Die

WWE struggled to gain any momentum for the Invasion storyline, but Shane and Stephanie McMahon did their best gaining heel heat. The flawed logic to the entire angle hurt it with the performers trying to make the most of it.

There was a backstage segment that crossed the line from heel heat to cringe-worthy television. Stephanie told the elderly Freddie Blassie that WWE was going to die soon, just like him. WWE used to do anything for heat, even if it made the audience uncomfortable.

8 Threatening Kaitlyn For Interrupting Her

The return to WWE television in the 2010s for Stephanie McMahon saw a lot of criticism for her segments. Most wrestlers to interact with Stephanie came off looking weak after she insulted them without any revenge from the in-ring performers.

This was shown perfectly when Kaitlyn was a victim of Stephanie’s character burying others. Stephanie and AJ Lee had an intense promo exchange before Kaitlyn interrupted with the rest of the women’s division to answer Lee’s comments. Despite leaving the ring, Stephanie threatened Kaitlyn to never interrupt her again for no reason.

7 Making Out With Eric Bischoff

WWE did a good job picking interesting choices of Eric Bischoff and Stephanie McMahon as the General Managers for the original brand split. The minds running Raw and SmackDown took part in a few great segments trying to outdo the other to represent the competition needed.

However, there was one backstage segment that had no logic and made fans cringe. Bischoff removed a Vince McMahon mask and started kissing Stephanie at a SmackDown Halloween party. Stephanie kissing him back made it weirder since they never had another romantic moment.

6 Slapping Big Show

The Authority forming as an act to feud with Daniel Bryan saw Stephanie McMahon developing feuds with other faces as well. Big Show was the wrestler selected to have a storyline with Triple H and Stephanie. The story involved Big Show losing money due to bad investments, which Stephanie held over his head.

Fans groaned during a segment that featured Stephanie slapping Big Show repeatedly for disrespecting Triple H. The largest WWE superstar standing and taking slap after slap by Stephanie showed how her character could harm other wrestlers’ credibility.

5 HLA Segment

WWE came up with a unique way to pay off the Eric Bischoff vs Stephanie McMahon General Manager feud involving other wrestlers. Eric Bischoff won a demand of his when 3-Minute Warning represented Raw in a victory over SmackDown’s Billy & Chuck.

Stephanie was forced to take part in an “HLA” segment of “hot lesbian action.” The idea itself was tacky, but WWE made it even more cringe-worthy with the idea in mind. Stephanie made out with a large person that was revealed to be Rikishi setting up Bischoff for an attack.

4 Announcing The Women's Royal Rumble Match

The rise of women’s wrestling has been a great thing for WWE in recent years, but there has been one negative involved. Stephanie McMahon being shoehorned into historic moments often felt forced and took away from the importance.

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WWE may have had their worst example of this when announcing the first women’s Royal Rumble match. Stephanie interrupted a slate of other women at odds to announce the news as everyone stood together and did the "Yes!" chant.

3 Dream Segment With Vince In Coma

WWE decided to come up with a strange comedic segment about the McMahon family with no context before or after. Vince McMahon woke up from a coma with then-WWE writer and celebrity actor Freddie Prinze Jr. as his doctor.

The joke was that Vince went into a coma as a result of wasting millions of dollars in Linda McMahon’s failed political campaign. This entire segment was revealed to be a dream by Stephanie waking up next to Triple H, happy that McMahon was still in a coma.

2 Competing For WWE Championship In Triple Threat Match

Stephanie McMahon didn’t place herself in as many matches as Shane McMahon did when both became successful characters. The in-ring portion of Stephanie’s career was minimal with usual workarounds to hide her flaws.

WWE went a little too far during an episode of Raw by making Stephanie a WWE Championship contender. Triple H defended the top prize in a triple threat match against Chris Jericho and Stephanie. WWE made fans fear Stephanie scoring the pin and becoming the top champ.

1 Accusing Daniel Bryan Of Cheating On Brie Bella

The feud between Stephanie McMahon and Brie Bella piggy backed off the Triple H vs Daniel Bryan angle. WWE created a lot of interest in the Stephanie vs Brie drama to make their SummerSlam 2014 match feel important.

The segments between Brie and Stephanie did great numbers until the final week took them off track. Stephanie introduced an unknown character played by Chelsea Green as Bryan’s physical therapist. The segment saw Chelsea claiming Bryan cheated on Brie with her as Stephanie’s latest plan.