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Ricky "The Dragon" Steamboat has participated in some of the most famously excellent matches of the 80s, including his three match series with Ric Flair for the NWA World Title and his victory over "Macho Man" Randy Savage for the Intercontinental Title at Wrestlemania 3. The match with Savage became legendary and was a huge rub for Steamboat, but then he lost the title out of nowhere to the Honky Tonk Man after a mere 65 days, and then was completely gone from the WWF within a year.
Why did Steamboat's momentum end so abruptly, and why was the Honky Tonk Man of all people chosen to beat Steamboat? Let's start with why Steamboat lost the title: Steamboat had asked for some time off to be with his wife since she was pregnant and expecting to give birth very shortly. Vince McMahon responded to the request by booking him to drop the title at the next TV taping, gave him over four months "off", and buried him for the remainder of his WWF run.
As to how Honky got the nod, the story that's been going around for years was that it was actually supposed to be Butch Reed (who was a much more imposing and believable badass), but Reed missed the taping where he was supposed to win the title and Honky got thrown in as the last minute replacement. Honky made his entire career off the 14 month reign that followed, but it ended up being little more than a footnote in Steamboat's highly respectable career.
2)John Cena loses the US Title to Orlando Jordan (March 1, 2005)
John Cena ascended to the top of WWE for the first time when he defeated JBL for the WWE Title at Wrestlemania 21, but he suffered a pretty embarrassing defeat on his way there. Cena was the US Champion as he built to the match with JBL, and since WWE wanted to get that title off of him before he won the WWE Title, they decided to have him lose it to JBL's Chief of Staff, Orlando Jordan.
Jordan was okay in the ring, but certainly not somebody who had the workrate or charisma to ever be much more than a low midcarder. The idea of him beating Cena (even with the help he needed from JBL to do it) seems insane in retrospect, but was even a stretch back before Cena was an unbeatable Superman. It's almost as surprising that the win over Cena began a nearly six month reign that finally ended in a (merciful) 30 second squash loss to Chris Benoit at Summerslam 2005.
Cena obviously went on to become the purveyor of hustle, loyalty, and respect we all know and love today, and Orlando Jordan toiled for another couple of years before being released. He briefly resurfaced in TNA and drew on his open bisexuality to present himself as a character with overtly sexual overtones, failed and left, and lost to the Ultimate Warrior in what was, as far as I know, Warrior's last match.
1)Stone Cold Steve Austin suffers repeated losses to Savio Vega (Early 1996)
Austin earns the top spot on this list due to the fact that he not only was defeated by somebody who never came close to the level of stardom and success Austin would attain, but he actually suffered many, many losses to this person. It's key to point out that the WWF saw NOTHING in Austin when he first came to work for them, an attitude that clearly changed eventually, but his feud with Savio Vega saw the man who would come to lead the Attitude Era looking at more ceilings than Michelangelo.
Savio Vega had been a major star in Puerto Rico and made it to the finals of the 1995 King of the Ring tournament, but had never really accomplished much beyond that, and mostly hung around the lower midcard after KOTR 95. Austin defeated Vega in their first major encounter at Wrestlemania 12, but that was the last victory Austin would score over Vega for many months.
Austin suffered his first televised loss in the WWF to Vega, who wrestled the match under a mask as the Caribbean Kid, on the April 13, 1996 episode of WWF Superstars. Vega followed that up with a win over Austin in the dark match at Good Friends, Better Enemies, defeated him in back-to-back strap matches at the Beware Of Dog events, and also defeated Austin in a S-L-E-W of matches on house shows and international tours in Germany and Kuwait.
Austin finally pinned Vega with the Stunner in the quarterfinals of the 1996 King of the Ring tournament (the televised debut of the Stunner, incidentally), and this would be where you'd expect me to say that Austin never lost to Vega again, but he actually continued losing to Vega in a series of no DQ matches on house shows for nearly another month until Austin won the King of the Ring tournament and FINALLY began to score regular wins over Vega on house shows.
Vega missed a scheduled rematch on the Buried Alive PPV, but Austin finally got the last laugh over a year later, pinning Vega to win the eight man main event at No Way Out 98. But even though Austin won that last encounter, Vega probably beat Austin five times as often as Austin beat Vega even if you take out all the house show matches, and that puts Vega amongst company like Bret Hart, Shawn Michaels, and the Undertaker as the only guys to ever have that kind of success against Austin.
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Though the losses suffered by Austin and everybody else in the list amounted to little more than minor speedbumps in their storied careers, they each had their own personal Larry Owings who, even if they never accomplished anything else in their careers (and most of them didn't), could at least spend their retirement pointing at the TV and saying "I beat that guy."
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