Shane McMahon has brought together some amazing moments throughout his time in the wrestling business, with the son of Vince McMahon being well known for taking some of the most insane bumps in the history of the industry. He has often been very popular amongst fans, but there's no doubt there have been moments that aren't perfect in his career as well.

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Whether it be awkward promos, a bad storyline, or just a strange moment inside the ring, there have been certain situations throughout his career that have left fans cringing when they watch him, which have left people shocked and at times embarrassed to be a fan.

10 Choking Backstage

Shane McMahon attacked backstage Cropped

Shane McMahon is well-known for a little bit of overacting at times, and when he was attacked in a backstage segment by Kevin Owens and Seth Rollins that is exactly what was on display. He got power bombed onto some of the steel set in the back, which was a normal segment to put over their rivalry.

But it became a cringeworthy moment because of Shane's reactions, as he went over the top with how he was selling it. Screaming out with big choking noises was meant to put over the pain he was in, but it ended up being an awkward moment for the fans to watch.

9 Hosting Raw Underground

Shane McMahon Raw Underground

Raw Underground was a very quick fad that WWE put on for a small period, and Shane McMahon was at the heart of that. He was the face of the idea, being the person that hosted it, but he wasn't the smartest choice to be in charge of what was supposed to be a hip, underground fight club.

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Seeing someone who is known for being a father stand next to a bunch of female dancers, or hearing him try to commentate throughout the fights was always an awkward situation. Fans didn't find him to be the right man for the role, and there were some cringeworthy moments from him.

8 Segments In Church

Shane McMahon and Vince McMahon in church

Shane McMahon and Vince McMahon's storyline against Shawn Michaels where the focus was on the fact HBK had found religion was not a good one. Adding religion into a wrestling storyline was never going to work out, and that was the case here as this ended up being an awkward rivalry.

But it was the segments that Shane and his father did inside of a church that made people cringe, as they went all out in mocking the fact that Michaels believed in God, with this being an odd call.

7 Braun Strowman's Report

Shane McMahon and Braun Strowman

Shane McMahon's rivalry against Braun Strowman was the most recent that he was involved in, but because it was so poor generally many people have forgotten about it already. One of the big issues came from the fact the rivalry was built around Shane thinking Braun was stupid just because he was tall.

His promos throughout the entire angle were cringey and made fans embarrassed to be watching the product as it felt like something that would be happening in a school playground. That was made even worse when he read out Strowman's 'report card,' which summed up why fans hated this feud.

6 Over The Top Referee

Shane McMahon special guest referee

Shane McMahon has been a special guest referee several times throughout his career, but at SummerSlam when he was involved in the storyline between Kevin Owens and AJ Styles he went over the top. Referees are supposed to be in the background, but that wasn't the case in this one.

He was over the top and got involved in the match so frequently that it ended up hurting the encounter overall. His actions were cringey to watch as he was trying too hard to inject himself into the situation, which wasn't a good thing at all.

5 Tell All Podcast

Mick Foley and Shane McMahon podcast

When the company was pushing the WWE Network heavily they created plenty of different special events and shows to make it important, one of which was a tell-all podcast between Mick Foley and Shane McMahon. However, it led to plenty of cringeworthy moments as Shane opened up about his career.

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One moment was when he opened up about his relationship with Vince McMahon, or when he spoke quite awkwardly about his connection to Triple H, which was always odd for people to watch.

4 Standing Up To Brock Lesnar

Brock Lesnar takes out Shane McMahon

Shane McMahon has always shown that he has no problem competing against anybody or taking any type of bumps throughout his career, but he is never someone that fans have seen as a main event player. Therefore when he tried to stand up to Brock Lesnar, a lot of fans instantly cringed.

This came after the Beast had attacked Randy Orton, and the fact that Shane attempted to deal with the situation is something that left audiences laughing, and feeling particularly cringeworthy.

3 Shane McMahon Vs. Mr. Mizanin

Shane McMahon and George Mizanin together

Shane McMahon's WrestleMania match against The Miz was an enjoyable one for the most part, but it isn't something that has gone down as one of his greatest contests that fans have never forgotten. But, it did lead to a cringey moment where The Miz's father ended up inside the ring.

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Seeing the two men square off was an odd experience, and it certainly wasn't something that most people would expect to witness at WrestleMania of all places. It was an odd spot, particularly due to the selling from Mr. Mizanin, but at least he got a WrestleMania moment.

2 Helping Vince McMahon With His Club

Shane McMahon helps the Kiss My Ass Club Cropped

There aren't many more cringeworthy and humiliating things than helping your father get other people to kiss his bare bottom, but that is what Shane McMahon was subjected to at points in WWE. That is not a situation any son wants to be put in, especially on national television.

To make matters worse, it was Triple H who was the victim when he was involved, keeping the entire situation within the family, for what must have been an incredibly awkward moment for all involved.

1 Shane McMahon Bullies Greg Hamilton

Shane McMahon and Greg Hamilton

Shane McMahon's 'Best In The World' gimmick was effective in terms of getting heat, but it is something that ended up dragging on for too long, and began to become irritating for fans. His treatment of Greg Hamilton was always a big part of the act as he would force him to stretch the words out for as long as possible.

That all worked nicely, but when he took it to the level of dragging Greg across the ring and up to the top of the entrance, it ended up going too far. Fans found the spot a little too far, and cringey to see a McMahon effectively roughing up and bullying a talent.