Even back in the 80s when Kayfabe was in full swing The Four Horsemen had fans: because they were so, so cool. As Raven put it, "There's a reason why Ric Flair keeps getting turned face - who wouldn't want to party with the Nature Boy?"
Then there was TNA's Fortune. Ric Flair, at his most insane yet, managing a bunch of TNA Originals who the audience at least respects and who can all go in the ring with the best of them, looking to take prominence back from outside invaders in the company they helped build? It didn't matter if they were the heels bloodying upEV2 every week or the faces screwingwithImmortal's plans (although Flair did turn on them during the latter), the crowd was always gonna side with them.
WWE's Maryse might be worth noting. Since her debut she has yet to display one redeeming quality. Even when she appeared to be nice to Gail Kim she was really laying down insults in French. True she is a Heel, but Maryse doesn't generate the animosity as other heels such as Michelle McCool or Layla, either from crowds or internet commentators despite the latter being better in the ring and actually having behaved decently before a Face-Heel Turn.
As of early 2010 Chris Jericho has been doing a form of this on WWE NXT, a show where eight "rookies" are paired with a "pro" mentor as they wrestle in hopes of winning a WWE contract. On the first episode he was rather displeased at his rookie Wade Barrett's verbal sucking up when introducing Jericho, but when it was Barrett wrestling on the fourth episode, Jericho at ringside went well above and beyond to put his rookie over, leading to this amusing exchange with the commentators as Barrett ground down his opponent that got Internet fans cheering:
Jericho: "Look at him meticulously wearing down the back of—"
Josh Matthews: I was just telling Cole the same thing, that you just said—"
Jericho: "You better be, pay attention—"
Matthews: "I told him—"
Jericho: "Say something!"
Matthews: "I know I... just did."
Jericho: "Do your job!" *slams table and stalks off*
Jericho: *turns around* "MORE!" *has to suppress a grin, while Cole and Matthews openly LOL on-air*
Back in '08-'09, they were trying to turn Randy Orton into a monster by having him viciously attack his opponents' family members, and then punting them in the skull. Except he was cheered when he did it to John Cena's father, and when he did it to the McMahon family while Triple H was handcuffed to the ropes, he got what was probably the loudest pop of the year (especially when he attacked Stephanie). Rumours were that the angle with him and Legacy was meant to have Ted DiBiase Jr. turn face but the fans rooted for Orton anyway which had him being booked as a face despite retaining many of his heel characteristics.
As it turns out, beating the crap out of the McMahons gets roughly the same reaction in 2009 as it did in 1999.
On a recent episode of Raw, Edge called Orton out on this; claiming that his (apparently insincere) dedication to the fans following returning from a career-threatening injury didn't net him the same kind of fan support Orton had, although Orton was playing the same selfish jerkass character he always was. Hell, immediately before Edge spoke, Orton got a massive pop for RKOing guest host Wayne Brady.
Established to possibly surreal levels when, in the midst of his face turn, he punted Jericho in the face and put him on the shelf. The crowd was actually calling for, "PUNT! PUNT! PUNT!"
Batista who at one point, long after turning his back on the fans, said that when he looks out into the audience he doesn't see people, just money. The next week fans were still showing up with Batista supporting signs because he's a good looking man.
Not just because he's a good-looking man. Most smarks were of the opinion that he was no good as a face, and that "Douchetista is the Best-tista". His final performances were almost sublime.
Mickie James has never actually been booed in WWE. Her initial character was a face who was Trish Stratus's biggest fan ever and she became increasingly obsessed with Trish even kissing her and saying she was in love with her. When Trish finally told her to back off Mickie went psycho and turned heel. However the crowds still cheered her and when she faced Trish at WrestleMania 22, the fans cheered for Mickie and booed Trish whenever she got offence in. Trish was never turned heel and Mickie remained a heel until after Trish's retirement in which she became a face by default when she feuded with Lita. She has always received brilliant reactions from the WWE fans so much that there was a near-riot at the Extreme Rules 2010 PPV which took place three days after her release.
The Fabulous Freebirds are likely the Trope Codifier, if not the Ur Example of this in wrestling. Despite being heels in the kayfabed 80s, they got cheered pretty much everywhere they went in the southern territories (except when they went up against a local favorite like the Von Erichs in Dallas). Their gimmick was that of a southern rock band in the vein of Lynyrd Skynyrd and they even used "Freebird" as their entrance music before recording their own song, "Badstreet, USA." Of course, it didn't hurt that they had a charismatic "frontman" in Michael P.S. Hayes (who actually was fond of wearing leather pants) as well as Terry "Bam Bam" Gordy, one of the greatest big men in the history of wrestling.
If the Freebirds were the Trope Codifier or Ur Example for the 80s, the example for the 90s would be "Stone Cold" Steve Austin. Following his Heel-Face Turn on Bret Hart, commentators like Vince McMahon and Jim Ross would often express astonishment as to why people went crazy over Austin despite his lack of morals and respect for anyone and anything. In fact, Austin would even admit that he did not care whether the fans cheered for him or not, but he did like the merchandise residuals that resulted from his sudden popularity.
Austin himself didn't even want to believe that his loss to Hart was a Heel Face Turn. Immediately after the WrestleMania 13 loss, Brian Pillman teased him by shouting "Stone Cold's a babyface!" across the backstage area, much to his displeasure.
ODB has never been a successful heel in TNA. She initially was one in 2007 but her trailer park Ladette character proved popular with fans and she was turned face. She was brought back as a heel in 2011 to feud with the very over Velvet Sky but after that was over she was turned face yet again because of how popular she was.
Kane deserves a mention. In the WWE, he has stalked and tormented people just for the hell of it and has even stated that his entire reason for being in the WWE was to rid himself of the Undertaker.
Undertaker has even admitted that two of his few joys are fighting alongside and against Kane. Taking that to his logical extreme, as we easily can because of their career's heated pattern, he doesn't care if he's helping Kane retain the World Heavyweight title or if he's trying to end Kane in order to take it from him. Sure, that means if he and Kane are both in a fight he's having fun, but there's no consistent show of regard for each other's well-being anywhere in this. Then again, they're demons.
CM Punk, after turning back heel in the middle of 2012 following a full year as the company's top babyface, continued to get cheered despite his character mutating from a cocky but genuine wrestling revolutionary to outright respect-demandingjackass. This was understandable at first, considering most of his heel run early on consisted of feuding with a Smug SuperBase Breaker and a face commentator prone to Moral Dissonance who both couldn't even admit that, being a long-running WWE Champion considered by many to be a leader for the young talent in the back, his claim to "Best in the World" status had some legs. Even Punk's later dickish habit of constantly interrupting legends was admissible, considering how many times a Hall of Famer would come up and tell him he had to fight John Cena for the infiniteth time to validate his career. However, the self-proclaimed habitual line stepper would achieve new lows not seen since the death of Eddie Guerrero, first when he taunted Jerry Lawler for his real-life heart attack the night of Lawler's official return to commentary, then when he interrupted The Undertaker's tribute to the late Paul Bearer less than a week after the latter's real-life death just to put himself over as the man who'll defeat Undertaker at WrestleMania, even using Bearer's name in the process. Even Vickie Guerrero felt he deserved to be punished. Yet fans still cheer for him.
The fact of the matter is, for all of his heel runs in the WWE, Punk will always be cheered for. Why? Because he's just so good at being bad.
Brock Lesnar is usually characterized as a remorseless monster bent on destruction, dominance, and bringing the pain, and even in Real Life came into the business with a huge mercenarial Jerk Jock attitude towards pretty much everything he does wrestling which even now is still there and which he admits to with no shame. But because he's such a freakishly talented athletic badass, a lot of people still love him. Granted, a lot of those people love seeing him as a HEEL because of all of the above, but still…