Saturday, April 13

The Most Embarrassing WWE Moment Every Year Of The 2000s

The 2000s was a fascinating decade in pro wrestling with WWE enduring many changes. Vince McMahon saw the company reach new heights with the purchases of WCW and ECW. The company went public and continued to experience new growth with top stars like Triple H, John Cena and The Undertaker leading the charge.

RELATED: 10 Wrestlers With The Most Combined Championship Wins In WWE In The 2000s

However, the story of WWE is that their longevity leads to many all-time great and all-time bad moments in wrestling history. The latter featured embarrassment coming their way in different forms throughout the decade. Each year from the 2000s will be viewed in depth to find the most embarrassing WWE moment from 2000 to 2009.

10 2000: Pat Patterson & Gerald Brisco Having Evening Gown Match

Pat Patterson and Gerald Brisco Hardcore Championship Cropped

WWE used some ideas in the early 2000s that they felt would be comedic in the moment, but these moments just ended up being an embarrassment decades later. King of the Ring 2000 featured an all-time bad WWE match that warranted zero PPV time.

RELATED: 5 Best Wrestling Crossovers Of The 2000s (& 5 Worst)

Pat Patterson and Gerald Brisco had an Evening Gown Match of all things attempting to rip a dress off each other for the Hardcore Championship. This was an instance Vince McMahon booking to his own comedic interests rather than what the audience wanted aka anything over this.

9 2001: Saturn Falling In Love With Moppy


Some of the embarrassing moments in WWE are intended by management for odd reasons. Saturn was a solid mid-carder for WWE until he got backstage heat at the wrong time. A match with an enhancement saw Saturn delivering some vicious hits in the ring after his local talent botched a move.

Saturn could have easily caused a lawsuit for WWE, so Vince McMahon decided to make an example out of him. The character of Saturn fell in love with a mop named Moppy to ditch manager Terri Runnels for the inanimate object. WWE reportedly did this to punish Saturn for his actions by having him dating an actual mop.

8 2002: Katie Vick Funeral Segment

Triple H Katie Vick

WWE created an embarrassing moment that will stand the test of time with the Katie Vick segment. Triple H feuding with Kane led to the heel claiming that he had a huge bombshell about Kane’s past. The claim from Triple H was that Kane was the driver as a teenager when he got into a car accident that killed his high school girlfriend.

However, one moment from this angle stands out above the rest as the most embarrassing moment of 2002. Triple H wore a Kane mask and humped a mannequin in a casket meant to be footage of the Katie Vick funeral from years prior. Fans and wrestlers still mock this segment to this day 20 years later.

7 2003: Al Wilson Passing Away During Honeymoon With Dawn Marie

Al Wilson Proposes To Dawn Marie Cropped

WWE went overboard with the soap opera storyline of Dawn Marie marrying her rival Torrie Wilson’s real-life father Al Wilson. The older Al being unable to avoid the temptation of Dawn’s beauty led to an embarrassing storyline that featured them getting married in their underwear.

WWE saved the most embarrassing moment for the honeymoon segments when they ended Smackdown with a death cliffhanger. Al passed out while consummating the marriage with Dawn to close the show where WWE eventually revealed he had died in canon.

6 2004: Brock Lesnar & Goldberg Booed Out Of Building

Brock Lesnar vs Goldberg at WrestleMania 20

Brock Lesnar and Goldberg were the ones suffering the most embarrassment with the worst moment of 2004 at WrestleMania 20. Madison Square Garden fans discovered the online leaks that week that both Goldberg and Brock were going to leave WWE after the match since it was the final on their respective contracts.

The audience showered both wrestlers with boos and disrespectful chants from the start of the match. Lesnar and Goldberg both looked frazzled as they had a terrible match with the crowd continuing to bury them. WWE even played into the embarrassment by having Steve Austin hit them both with stunners after the match.

5 2005: Big Show Losing Sumo Match To Akebono

Big Show Vs Akebono

WWE has placed Big Show in many embarrassing moments throughout his career. Unfortunately, one of them came on the biggest stage of WrestleMania 21 when Vince McMahon had a unique idea. Legendary sumo wrestler Akebono was booked to have the first WWE sumo match.

RELATED: 5 Big Risks WWE Took In The 2000s That Paid Off (& 5 That Backfired)

Big Show tried his best, but he was destroyed by the professional sumo wrestler as expected. Big Show getting shoved out of the ring in the revealing outfit by Akebono has been used in various videos of other wrestlers attempting to embarrass him in feuds to show how bad it was.

4 2006: December To Dismember PPV

December To Dismember Elimination Chamber 2006 Cropped

There were a few moments that could be argued as the most embarrassing of 2006 like D-Generation X attacking the Spirit Squad with slime or Vince McMahon feuding with God. However, the ECW project stands out as the biggest disaster since WWE failed at making it an effective third brand.

December to Dismember 2006 was the only brand exclusive PPV that ECW received for their talent. Everything about the show failed with few matches announced beforehand and horribly low PPV sales. The entire show missed the mark with mostly horrible matches and a dead crowd vibe to end all plans for future ECW PPVs.

3 2007: Fake Donald Trump Vs Fake Rosie O’Donnell

Donald Trump vs Rosie O'Donnell in WWE

The celebrity drama between Donald Trump and Rosie O’Donnell in 2007 saw them insulting the other in interviews. Vince McMahon was amused by this to the point of wanting to book a match on Raw with unknown wrestlers pretending to be Donald and Rosie.

Ace Steel played Trump for the embarrassing match in the suit and wig attempting to fight a wrestler impersonating Rosie. Many fans felt that WWE not having competition was worst for reaching this point of getting to book pointless things to amuse Vince’s humor since he could put anything he wanted on TV.

2 2008: Using Jeff Hardy Drug History To Explain Absence At Survivor Series

Vladimir Kozlov v Triple H v Edge Survivor Series 2008 Cropped

Survivor Series 2008 had a match that many viewed as the worst of that entire year. Triple H was initially scheduled to defend the WWE Championship against Vladimir Kozlov and Jeff Hardy. However, WWE started reporting throughout the day that Hardy’s status was in the air after being found unconscious in his hotel room.

This was done to set up Edge replacing him when showing up at the end of a boring Triple H vs Kozlov match to win the WWE Championship. WWE received some criticism for the Hardy storyline since many felt it implied that he had a drug overdose in his hotel given his history. Dave Meltzer’s Wrestling Observer Newsletter awards saw this winning Most Disgusting Promotional Tactic of 2008.

1 2009: Santino Winning “Miss WrestleMania” Battle Royal

WrestleMania 25 - Santina Marella Cropped

WWE rarely utilized the women’s division outside of battle royals and lumberjack matches in the 2000s at WrestleMania events since the card space was tougher to get. WrestleMania 25 featured a “Miss WrestleMania” battle royal with many women from the present and past competing over the honor.

Santino Marella pretending to be his sister named Santina won the battle royal and started appearing with the Miss WrestleMania gimmick. The women’s division all being placed into a thankless battle royal would be bad enough, but WWE booking a male wrestler to win it was embarrassing for all involved.

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