A Trickster who seems to have the element of subtlety only in specific clumps. Sometimes the spiritual cousin of the Punch Clock Villain, sometimes a variation on the Enigmatic Minion or a more amenable Les Collaborateurs.
Merely seeing this guy and having a conversation with him for five minutes already cues the hero he shouldn't be trusted too much. He may even openly work for the bad guys, and say threatening things in a non-directed way. Hey, it's his job, nothing personal. And why shouldn't he enjoy what he does?
Your major safety is he likes being entertained, so sometimes will willingly subvert his bosses if he has his own agenda and help you — or at least not hinder you. He'll get you into trouble, but he'll assure you afterwards he knew you could deal with it. He'll betray you, but he won't tell your enemies all they really need to know about you.
This is Older Than Print — the archetypical example is the Prose Edda's depiction (which, for whatever it's worth, diverges markedly from that within the older Poetic Eddas) of the Norse god Loki. Much like the Lovable Traitor, it's a misconception to think of him simply as evil — although he's not above being The Jester in the most classy way he can.
Compare Reliable Traitor, Wild Card, Heel-Face Revolving Door and Double Agent.
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Anime and Manga
Xellos, fan-favorite demon and self-proclaimed trickster priest from Slayers. Always an amiable sort, Xellos will often manage to passively "betray" his allies by oops, allowing them to die horribly, alternately help and hinder our heroes and merrily subvert the status quo to his own amusement and greater purpose - sometimes all in the course of one episode.
Lupin III believes this of all women: "Betrayal is yet another of women's accessories.". The character of Fujiko is agreed to be a traitor by the entire group, although only Lupin admits her to be loveable.
Sergeant Major Kululu from Keroro Gunsou. He's technically the superior officer, but since he's so sketchy, no one wants to follow him so he's the intelligence officer.
Kabuto Yakushi is so ridiculously untrustworthy that even the villain he swore unending loyalty to claims that there's no telling what he'll pull when he's on his own. He can, and has, betrayed everybody he's ever met at least once with a smile on his face and may be on his way to Big Bad status at the moment.
Itachi Uchiha. Even before his true intentions were revealed.
Bleach: Gin Ichimaru. He has a blatant case of Chronic Backstabbing Disorder, and even deliberately joined Aizen to backstab him (it looked to be the easiest way to get to him).
Vice-Warden Hannyabal from One Piece babbles very often that he wants Warden Magellan's position, which is a Running Gag. Everybody in Impel Down knows it, but they simply don't care. Magellan even says that he wants Hannyabal as his successor. After the great outbreak in Impel Down and the Time Skip, it's revealed Hannyabal has become the warden, and Magellan the vice-warden.
The Fixer is often this for the Thunderbolts. He frequently switches sides or abandons his friends to die to save his own skin. He doesn't care about money, power, revenge, altruism, duty or loyalty. He only cares about the challenge of a task, proving he's the smartest one in the room and staying alive. He will help save the world or help conquer it provided he is given an interesting technical challenge to figure out.
Valentine in MirrorMask. But he redeems himself completely.
Inverted by D'Arcy in The Perils of Gwendoline in the Land of the Yik-Yak. Originally the traitor who led to Gwendoline getting captured by Amazons. When he tells Gwendoline he is willing to betray the Queen for her sake, she exclaims in exasperation, "You betray everybody!"
CaptainJack Sparrow. In the course of the first film, he ends up allied with and conspiring against every single character down to and including the monkey.
The Marquis De Carabas from Neverwhere, by Neil Gaiman. Though, more accurately, Hunter is the true mole of the group, and is considerably likable. The Marquis on the other hand can be relied upon when he owes you (or your father) a favor - though he much prefers you to owe him.
Speaking of Neil Gaiman: Crowley of Good Omens, "An angel who did not so much fall as saunter vaguely downwards".
Long John Silver (and a great many more of Stevenson's characters) in Treasure Island.
Varys and Littlefinger in A Song of Ice and Fire. As a man of low nobility and no martial prowess and a foreign commoner and eunuch respectively, they're not trusted so much as underestimated by the rulers of the Seven Kingdoms.
Rupert of Hentzau, one of the main antagonists in The Prisoner of Zenda, will stab just about anybody - hero or villain, whichever seems most fun - in the back, with an amiable smile on his face. The women of Ruritania have a collective crush on him; even the hero keeps bringing up his positive qualities.
Dustfinger, of Inkheart, betrays them about twice in the first book, yet each time, and AFTER, they trust him readily enough
Arguably, Krager in David Eddings' The Elenium. He's openly and unrepentently on the side of the bad guys (he's basically The Dragon's sidekick), but he has no real loyalty to them, he just thinks they're going to win. If the heroes capture him, he'll trade information for his life, and it's always good information, so they'll accept the deal the next time they capture him. Thanks to this, he gets away with murder (literally) for the whole series, since by the time his usefulness is spent (meaning the heroes can kill him) it's obvious he's dying of liver disease.
Live Action TV
Jayne Cobb from Firefly may have made a deal with the bad guy in the pilot episode and tries to turn Simon and River over to the Feds in "Ariel", but only out of foolish greed than genuine malice and he comes to regret the latter incident.
Harmony, bimbo cheerleader-turned-vampire-turned-perky-executive-assistant, gets a letter of recommendation from Angel even after she betrays him. To be fair, he was counting on her doing it anyway, and she was a pretty good secretary...
And let's be fair, the soulless vampire probably decided to betray Angel after she saw Fred, who she liked, die due to Gunn's error and Angel and Spike's unwillingness to trade Fred's life for countless others, and latter events like Angel's willingness to sacrifice his allies proved her right.
Angel's lack of respect towards Merl is somewhat justifiable given that in his first appearance, Merl tricked him into killing a pregnant woman's demon guardian so that she'd be vulnerable to bounty hunters.
Supernatural has Bela, a highly-successful thief of supernatural items who has occasional run-ins with Sam and Dean. She becomes much more of a Lovable Rogue, however, after she willingly (if at gunpoint) gave Sam and Dean's whereabouts to a Knight Templar hunter who wanted to kill them. Dean calls her after the two narrowly escape with their lives, and when she proves unrepentant about the affair, Dean tells her in no uncertain terms that if he ever sees her again, he'll kill her. Then he hangs up. A few minutes later, Bela calls back with an apologetic non-apology and the hunter's location as recompense.
Dark Angel's Alec, at least before he becomes a full-on good guy, which is a gradual process.
In the Doctor Who story "The Daleks' Master Plan," the Meddling Monk makes a reappearance for a few episodes. He goes around with the heroes, then helps the Daleks in order to save his own skin. Then when the heroes show their contempt for him, he says something like "I hoped I was convincing enough to fool the Daleks, but I didn't think even you would be fooled. This destroys my faith in humanity, it really does."
Amanda from the Highlander TV series has a habit of getting Duncan Macleod into various kinds of trouble, but never so bad that it's not pretty likely he'll survive it. She really does love him, in her own twisted way, something she is reluctant to admit even to herself, but which pretty much everybody around them recognizes. Duncan's problem is that it's mutual...
Bart Rathbone from Adventures in Odyssey. Little more than a conniving businessman, not above helping the out-and-out villains at one point, and generally the opposite of everything the show stands for. But... it's just so hard not to love the guy sometimes. (It helps that, in practice, he's generally harmless. And he did turn on the bad guys eventually, albeit for selfish reasons.)
Some of the members of Organization XIII in the Kingdom Hearts are examples, like Axel and Demyx. Axel epitomizes of this during Chain of Memories.
Jill, a Wyvern Rider in the Fire Emblem series, becomes a traitor not once, but three times. First, she leaves Daein to spy on Ike in Path of Radiance, which leads to her altogether abandoning her country and joining the Crimean Army. Then, in Radiant Dawn, she's fighting Crimea on Daein's side. Then, it's possible to make her betray Daein and join Crimea again. Luckily, she's heroic enough (and a spectacular unit to boot) that the audience overlooks her constant flip-flopping.
In Path of Radiance, she sets two milestones. If you have her on your active team during the mission where you face her father, and they come in contact with each other, she'll switch sides. She has now become the first, and so far only, character unit to be recruitable by the enemy. The second milestone she sets? If she has a strong enough Support bond with Mist or Lethe, they can re-recruit her back to the party after her Face-Heel Turn. So not only is she amazingly conflicted and a good unit, she's damn cute too.
Naesala, too. In Path of Radiance, he basically sells Reyson into slavery—with the intention of later freeing him, but the heroes beat him to it. He then later sneaks into Gritnea Tower disguised as a Daein soldier in order to save Leanne while the guards are occupied with fighting the heroes, but insists he's still not a good guy. Come Radiant Dawn, and he has betrayed the Laguz Alliance yet again, once more leading to death threats from Tibarn—but once again, he had a perfectly good reason for his actions; Kilvas was subject to a Blood Pact. Which, when you think about it, might explain his actions in Path of Radiance as well... (His time as a villain during that game starts at Chapter 13, when the heroes first cross into Begnion, and ends in Chapter 19, the last chapter before they cross into Daein. And Oliver, the slave trader he sold Reyson to, was a Begnion senator. All of his villainous actions could conceivably be traced back to his Blood Pact with Lekain.)
Some consider Drakuru from World of Warcraft to be one of these. Sure, he tries to zombify you against your will, but look at all the power serving the Big Bad got him! Why wouldn't he want to share it with his old friend the Unwitting Pawn? Besides, it's one of the cooler quest chains in an expansion filled with cool quest chains.
When his true intentions are revealed he definetly fits this trope: He tells you he's used you to bring the ice trolls under the sway of the Lich King, and gets transformed into a death knight as a reward. Then he thanks you for helping him and lets you go unharmed.
Zevran from Dragon Age: Origins is this Hell-Bent for Leather doused in Fetish Fuel. As the assassin who just tried to murder them, it takes a long time for the rest of the party to come to trust him and initially consider the Warden insane for sparing his life and letting him join the party.
Tales of Vesperia has Raven/Captain Schwann. Capped off when, to rescue one party member captured due to betrayal, every human party member present punches him in the gut. Later, it's revealed that said captured party member also punched him after the rescue, so as to not be left out.
Veilchen the Smoke Knight from Girl Genius. Even the Jagermonsters are impressed at his professionalism as he leaves them to die in an inescapable pit.
Bender from Futurama. Most of the time his "Kill all humans" isn't meant seriously. Although in "A Pharaoh to Remember" he loses the Lovable part and becomes The Quisling (and later, after he scams his way into becoming the new Pharaoh, Drunk with Power).
Legend Of Korra Oh, Varrick. He only gets more loveable after being put in prison. Nobody seems capable of holding any bitterness towards him, and he even makes up for it with a heartless war machine, Zhu Li (the battleship, not the cute assistant). Bolin definitely misses him and wishes he were there to lighten the mood.