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.
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.
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.
For said brother's part, The Undertaker can usually be reliably cited as a standing model of dark justice: however, he has at times abused his macabre image of power to commit frightening acts of evil, almost bordering on Beware the Superman. Take, for example, the time period in which he became a minister of darkness, claiming he set the fire at the funeral home on purpose, trying to embalm "Stone Cold" Steve Austin alive on a table backstage, assembling a Hollywood Sataniccult which routinely engaged in kidnapping and symbolic Human Sacrifice of men and women alike, including Vince McMahon's daughter Stephanie—and somehow ended up merging its way into a plot to take the title off Steve Austin by the very same mad chairman whose company they originally wanted to take over. Or the period in which he forced a guy to literally kiss Vince's ass, assaulted a legend's son unprovoked, put a family in the hospital, and beat the hell out of another legend with a chain just because he felt he wasn't getting enough respect. He was clearly the heel in those time periods, yet the respect he commanded kept him cheered through most of it. At other points in time he's also at least symbolically burned a man to Hell, routinely Tombstoned physically lesser parties such as women and managers for getting in his path, and nearly killedsomeone at the Great American Bash two consecutive years—but those are more painting the hero black.
The dynamic between Kane and Undertaker is particularly unhealthy. Despite the fact that Kane has stated at one time that his entire reason for being in the WWE was to rid himself of Undertaker, Taker himself has 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. If they're together, they're not just content with winning—they're out to make a couple of unlucky sods' lives physically miserable as some sort of twisted friendly competition with each other. If they're against each other, they're trying to destroy each other for months, and it's almost guaranteed one of them is going away for awhile when it's all over. Yet, despite how unhealthy it is for everyone around, people still never tire of seeing the Brothers of Destruction sharing a wrestling ring. Then again, they're demons.
The Rottweilers eventually reached this status in Ring of Honor, especially after their second incarnation came with the addition of the company's first champion. But the oddest case of this was Homicide. The crowds loathed Konnan, but didn't mind Homicide being associated with him or using a theme composed by him. He was given another evil manager in "the devil's son in law" Julius Smokes, which still didn't work. Homicide cussed out the fans specifically for chanting in his support at Generation Next, which only made it continue. "Ring Of Homicide" revolved around him assaulting everyone in the company that had so much as annoyed him with a fork and by that time no one even tried to pretend he wasn't a baby face.
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.
WWE's Maryse might be worth noting. During her time in WWE she never displayed 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 didn'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.
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.
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 an 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!"
In 2010 Chris Jericho did a form of this on WWE NXT, which at the time was a show where eight "rookies" were paired with a "pro" mentor as they wrestled 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: *walking from the table* "Talk about Barrett!"
Michael Cole: "We are!"
Jericho: *turns around* "MORE!" *has to suppress a grin, while Cole and Matthews openly LOL on-air*
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.
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 cheered 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 mercenary Jerk Jock attitude towards 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… between his sporadic appearances since his "return" to WWE, his popularity has dwindled somewhat though. After breaking The Undertaker's streak at WrestleManiaXXX on April 6, 2014, though, the X-Pac Heat picked up steam to such a degree that even Lesnar was surprised. Then he destroyed John Cena at SummerSlam four months later and won back the crowd.
Another case from ROH. Since the infamous low blow where he turned heel on El Generico, Kevin Steen has been one of the biggest cases of Draco in Leather Pants EVER. His hatred against Generico and Jim Cornette drove him to the lengths of pulling a Heel-Face Door Slam on Jimmy Jacobs and Steve Corino and getting them to band together with him in an alliance called SCUM—for the purpose of destroying Ring of Honor all over his grudge. He has threatened to Package Piledrive ROH president Cary Silkin into the next world, spat in the face of Jay Lethal's mother, commandeered the ROH World Title for nearly a year and rubbed everybody's face in it—and again, set out to destroy Ring of Honor over his hatred of TWO MEN. Yet despite this, almost every action of his gets cheered even against faces the fans have no desire to root against, and even if he is trashing on an arena crowd and calling them hypocrites over this very thing, "The question was never if Steen will, but how loud the fans'll be callin' 'KILL STEEN KILL!'" This has only continued since he arrived on WWE NXT as Kevin Owens and resumed his reign of terror by betraying Sami Zayn (again).
In 2013, Act Yasukawa turned heel on her Trouble 2 Maker stable mates by smacking Yoshiko with a steel chair after they failed to win the Artist Of Stardom titles with Natsuki*Taiyo and joined Kimura Monster Gun. Well, she tried anyway but the fans kept treating her like a baby face and wildly cheered for her. She was still trying, unsuccessfully, to get heat the next year, going so far as to bust open Kris Wolf(who was technically another stablemate). She would eventually spit rum on a fan chanting her name, which lead to more fans chanting her name and lining up to be spat on.
Eddie Guerrero's career motto since his WCW days was all about cheating, openly flaunting all sorts of dishonorable tactics as a form of pride. He was willing to sell out his fellow luchadors by unmasking them for an investigation and even drove his own nephew into madness by trying to rope him into following his ways (though Chavo eventually did so willingly years later in WWE). As his feud with Rey Mysterio Jr. in 2005 showed, if he got particularly driven about something he could be prone to obsessive, sociopathic tendencies and absolutely vile measures. Yet because of his talent, his charm, and the fact that in real life he was a recovered drug addict and a born-again Christian who always had love for the people around him, his character got away with a lot of crap in the eyes of fans, so much so that it literally took the stipulation of putting the custody of Rey Mysterio's son on the line following Eddie's claim that Dominick was actually his for people to universally want Rey to beat Eddie in a match that year. And that's all BEFORE the man's death.