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If you go up to Billy Gunn and mention the words "Rock-a-Billy", chances are you're going to make him very angry. He's since said that the gimmick had potential, but they used the wrong outfit and music. Mercifully, it was ended after a few weeks and he quickly enjoyed more success as part of the New Age Outlaws.
Former WWE Diva Stacy "The Kat" Carter was reportedly very ashamed of her time in WWE and even had her real name removed from various wrestling websites. However, she has since embraced her history and started making several indie appearances, selling her merchandise on eBay and sharing personal photos from her time there. She later clarified that it came from bad memories surrounding her divorce with Jerry Lawler (which happened only a few months after her release) and advice from her real estate colleagues.
Subverted with Trish Stratus in regards to the segment where she had to crawl around the ring and bark like a dog, as she's pointed out the fact that it was part of a storyline and that her character ultimately got revenge on Vince for humiliating her like that.
Ironically, the WWE is quite ashamed of said "Bark Like a Dog" moment, along with the infamous Katie Vick angle (which HHH defended at first before realizing how much everyone hated it) and other tasteless bits from the Attitude Era; when Linda McMahon ran for the US Senate, an attempt was launched by WWE to eliminate all traces of these moments from YouTube so that they could not be used against her, which failed miserably when her opponents kept reminding people about them.
Trish does have one case of Old Shame played straight: the infamous moment known simply as "That Jackie Gayda Match". For the uninitiated, it was a match on Monday Night RAW that pitted Stratus and John Bradshaw Layfield against Christopher Nowinski and Jackie Gayda, who were both contestants on WWE Tough Enough 2 and still very green in the ring. The match was a disaster from beginning to end and, when Stratus finally pinned Gayda for the win (even Jim Ross called it a Mercy Kill by that point), she was visibly pissed off by the sheer number of botches that Gayda had committed. JBL himself has said that it was the worst match he had ever participated in.
Gail Kim has no love for her second run in WWE from 2008-2011, due to the horrible way the women were treated with regards to match times, booking and storylines.
During the early days of the nWo, Kevin Nash and Scott Hall cut a promo with The Giant in which Hall made an unscripted reference to how Giant had originally been billed as the son of Andre the Giant. The Giant immediately shot a Death Glare at Hall and said "Don't you dare go there again".
Nash had his own moment when, in 2011, CM Punk brought up his alter-ego "Oz", arguably one of the most embarrassing moments of WCW history from the early '90s. Same with John Laurinaitis (AKA Johnny Ace), as Punk made references to his failed run in WCW by bringing up his past with Shane Douglas as part of the much-reviled "Dynamic Dudes".
Terry Taylor does not fondly remember his time in the WWF, where he was known as "The Red Rooster".
John Zandig of CZW is famous for delivering a memorably insane promo that was immortalized in Botchamania. However, according to a story from Maffew, DJ Hyde learned the hard way during a lunch meeting with Zandig that he's not too proud of it. Fortunately for Maffew, he learned of this before going to a CZW show and trying to get an intro out of Zandig.
In 1993, Mick Foley, under his Cactus Jack gimmick, did a storyline where, after a particularly brutal match with Big Van Vader, he suffered amnesia and was living in the streets of Cleveland as a destitute bum who thought he was an ex-sailor. Foley urged fans to destroy any footage of the storyline in his first book, and it is never brought up in any DVDs devoted to Foley.
Never, ever bring up "Mean Mark Callous" to The Undertaker.
Bret Hart is deeply ashamed of the "I Quit" match he had against Bob Backlund at WrestleMania XI. While he deeply respected Backlund's skills, not only did Bret feel that the frequent submission holds "stunk the building out", but Roddy Piper, the special guest referee, kept sticking a live microphone in their faces and yelling "Whaddya say?" in an over-the-top voice that came off as plain goofy, making the match impossible to take seriously. According to Bret, "nobody laughs during my matches unless I want them to!".
He's also not too fond of an old cowboy gimmick he did early in his career.
The Rock doesn't like to talk about his "Rocky Maivia" gimmick in any positive way. His WWE bio doesn't even mention the gimmick by name.