The 5 Most Awkward Matches in WWE History

There are some WWE matches that are remembered for being classics; there are others that are remembered for being particularly bad. But there's a rarer breed of bout that is just awkward to watch.

This is often due to the context of the match, even if the performers have done the best they could with what they were given.

Maybe the audience didn't like who was being pushed. Maybe they were mad at the performers for backstage reasons that had nothing to do with the characters they were portraying. Or maybe the match's concept was broken from the outset, and there was no fixing it in the first place.

In 2013, WWE spotlighted "the most awkward" match in the company's history: the 2001 Raw showdown between Buff Bagwell and Booker T. It was a WCW match that was the main event of the night.

However, the problem was that the majority of the crowd were unfamiliar with the two WCW competitors and still viewed the southern-based promotion as "enemies," thanks to the Monday Night Wars. And fittingly, this was also the last time Vince McMahon attempted running a WCW program on a WWE show.

Here are five other awkward WWE matches. At best, they might make you cringe; at worst, they might make you embarrassed to be a fan. 

In 2004, Goldberg was psychologically spent and Brock Lesnar wanted to try out for the NFL. Both men decided to leave WWE, and their last match would be their showdown at WrestleMania XX.

On paper, it was once-in-a-lifetime clash of giants befitting The Grandest Stage of Them All.

However, the Madison Square Garden audience booed both performers for their decisions to leave WWE. The backlash rattled both men, who spent more time grappling and hugging each other than fighting.

The only performer to get over was special guest referee "Stone Cold" Steve Austin, who Stunnered both men to mercifully close the segment.

The New Generation era of WWE—which preceded the Attitude Era—might as well have been called the Career Gimmick era.

It was a dark age for hokey hilarity, and this match was Exhibit A.

Phantasio, a wrestling illusionist, used amateur magic tricks to bewilder his opponent. The crowd was largely bored and confused as to what was happening. And poor Gorilla Monsoon, who was the play-by-play announcer at the time, had to carry on about the discount magic tricks like he just saw a miracle.

It would be the character's last match with the company.

File this gimmick in the same file as Mantaur and T.L. Hopper.

There was so much cringeworthy stuff in this WrestleMania XXV Battle Royal in 2009 to crown Miss WrestleMania.

First, the women got no individual introductions and all came out in one massive group during the live Kid Rock performance.

And once the singing was done, the women just started brawling without ceremony and the ring announcer yelling out the rules.

Who was involved in the match? Who were the surprise guests? What were the rules? A casual fan had no idea what they were looking at.

And to make matters worse, the match was won by Santino Marella wearing a skirt and top.

WWE managed to get Hillary Clinton, John McCain and Barack Obama to cut pre-recorded promos ahead of the U.S. presidential election in 2008. It was the sort of mainstream acceptance Vince McMahon had always appeared to crave.

That's why it was so baffling that he decided to keep the "match" between the Hillary and Obama impersonators (with a Bill Clinton impersonator at ringside), which aired immediately after the promos.

This was the sort of thing you did if the candidates declined to come on the show. The juxtaposition, between the real candidates and their corny doubles, came off as tacky and hopelessly out of touch.

So close to respectability, and yet so far.

Vince McMahon couldn't wrestle and Bret Hart couldn't take bumps (owing to a stroke and prior wrestling injuries). Put that together, and you have a match everyone wanted to see in theory but was way past its prime in practice.

It was also a lumberjack match, which meant the extended members of the Hart family surrounded the ring, pounded the canvas and awkwardly cheered for Bret as he delivered a protracted beatdown.

It was over the top and unnecessary. All the fans wanted was for Hart to hook in the Sharpshooter, and he didn't even need a match to get that done.

Although the match's finish fulfilled that part of the bargain, it was all a tedious letdown.