Refuge in Audacity/Professional Wrestling

In 1991, Barry Darsow (formerly Smash of the tag team Demolition) was repackaged by the WWE as "Repo Man", which was Exactly What It Says on the Tin. A horrible gimmick that was presumably aimed at provoking cheap heat from deadbeats, Darsow played the character so ridiculously over the top that it was hard to hate him.
Every single thing that D Generation X has ever done. There is not enough time in a week to list all of the jaw-dropping, boundary-crossing hijinks.
In late 2005, WWE was at a loss for how to make the crowd root for John Cena and boo Kurt Angle. They tried all of the cheapest, most offensive tricks in the wrestling playbook to make Angle the bad guy: he began bashing America and was given an Arabic manager to interfere in his matches, all the while playing the xenophobic angle to attract as much cheap heat as possible. It failed because nobody was buying an anti-American Kurt Angle, and eventually Angle lampshaded the difficulty in getting people to hate him by going even further into offensive territory. The resulting promo is generally held to be hilarious because nobody can take it seriously:

Kurt Angle: First of all, I'd like to say that: I hope the US loses the war in Iraq. And, uh, while I'm at it, I think the greatest country in the world is...France! Y'know, truth be told, I'm not a very big fan of..."the black people." And if I would go back in time, the one person in history I'd like to make tap out would have to be...Jesus! ...The point is, I can say anything I want to these idiots, and they'll still cheer for me!

—* Right on cue, the crowd cheers enthusiastically*

- After this, WWE finally gave up on trying to make Angle a heel. But they only did that when Batista got injured and Angle was switched to SD hastily. Maybe they weren't even planning on stopping there.
- Unfortunate Implications: French people are comparable to America-haters, racists, and anti-Christians?
  - This occurred not long after the war in Iraq started. Since France didn't want to go to war, France became something of a punchline (this occurred around the same time as the "Freedom Fries" fiasco.)
Katie Vick. Triple H pretending to be Kane, having sex with his dead girlfriend in a casket.
The WWE's Most Intimate Relationships Revealed segment on Monday Night Raw when Jerry Springer hosted was very much this trope. It started with Jerry revealing that Kelly Kelly was secretly pregnant. Kelly reveals that she had a few drinks with Santino Marella and things happened. After Santino declared that he was the father, Kelly revealed that she needed someone to finish the job, Michael Cole. This results in the possibility that Jerry Lawler may be the father, but Springer shoots that down because Jerry likes to pick up his chicks from recess. This brings out the Bella Twins and Nikki reveals that Brie is a man, resulting in a Cat Fight. Jerry steers that topic back to Kelly, and this brings out Chris Masters to reveal that he slept with Kelly, and this brings out his very angry girlfriend Eve Torres who also reveals she had an affair with THE GREAT KHALI! With almost all of the comedy characters accounted for, Jerry Springer reveals that he has the pregnancy test results back. Santino questions this possibility seeing as though this only happened three days ago, and Springer simply says, "I'm Jerry Springer." The results reveal the father to be Hornswoggle, and this is too much for Jerry Springer of all people, and he begins to leave in disgust. Jerry Lawler then reveals that the entire segment was a prank and that the Great Khali probably does not even know what's happening. Khali's translator says that Khali felt like the audience in that this was a giant waste of time. To close out the segment, Lawler turns the tables on Jerry and reveals Springer's secret fling, MAE YOUNG! RAW goes to a commercial as Springer makes out with Mae.
Stone Cold Steve Austin owned this trope.
- CM Punk is not far behind.