"Now; I did a job. Got nothing but trouble since I did it, not to mention more than a few unkind words as regard to my character. So let me make this abundantly clear: I do the job... and then I get paid. Go run your little world."
Lupin III follows the exploits of the titular thief as he attempts to woo Fujiko (or any other attractive lady), and steal anything that amuses him. A bit less loveable in the manga, but often more of a rogue.
Blue, from Pokémon Special, fits this description at first. She consistently cheats and lies, and shows absolutely no signs of a conscience or caring for anyone but herself, yet she and the main character manage to remain on almost friendly terms. She gets nicer and gives up thievery by the end of the first arc, but still keeps some loveable and roguish qualities.
Androids 17 and 18 of Dragon Ball Z — in the main timeline, at least. In Trunk's timeline, they're sociopathic killers.
Ali al-Saachez from Mobile Suit Gundam 00 is a subversion; his men love him for his fun nature, and he does take care of them, often fighting Gundams by himself because he knows only he can match them in direct combat. However, he's also a Blood Knight who cares only for chaos and slaughter; if it's not him causing a civil war, it's making children kill their parents to prove their devotion to the cause, or just random murder for the sake of it.
Most of the principal cast of Baccano!, especially Isaac and Miria.
In Fushigi Yuugi, the rough and brash thief Tasuki's first appearance consists of kidnapping the heroine Miaka, unleashing ghost wolves against the heroes who try to stop him, and later faking his own death to avoid joining the heroes. However, he later shows up to save the heroes from zombies and becomes completely dedicated to their cause, to the point of nearly making a Heroic Sacrifice on Miaka's behalf.
Plus, the actual thieving of Tasuki's thief gang is easy to ignore, since they border on being The Pirates Who Don't Do Anything anyway (except when they briefly serve as The Cavalry later in the series, which makes their thieving even easier to ignore).
Dark in D.N.Angel most definitely fits this trope!
InuYasha: Miroku has no qualms about lying, drinking, womanizing, conning and stealing, being determined to enjoy life to its fullest, but he later shows that he's also loyal, wise, and is ready to help and protect others even with his own life. Although there is pressure on him to produce an heir that can avenge his death (and also inherit the same curse), his womanizing is an inherited character flaw. His grandfather's womanizing nature is what allowed his Arch-Enemy to curse the family line in the first place. Miroku's flaws therefore run in the family.
Hellblazer: John Constantine sometimes qualifies — if you're watching from a distance. If you're personally acquainted with him, you'd be more inclined to say that he is a prick, since sometimes his only goal is taking care of his own interests, and he can exploit others ruthlessly. But most of the time he's saving the world, which makes him an anti-hero.
The snarky outcast drow rogue Downer, the protagonist of the comics Downer: Wandering Monster and Downer: Fool's Errand by Kyle Stanley Hunter (formerly published in DUNGEON Magazine). A down on his luck "proven loser" who survives by his wit, quick tongue, quick blade and quick reflexes (and mainly by running the hell away when outnumbered, unless he's sufficiently pissed off that he decides to indulge his inner Badass and take on a whole bunch of enemies by himself). Although he considers himself an "evil bastard" who puts his own survival first and claims he's "always prepared to be screwed over by his friends", Downer has demonstrated amazing loyalty to friends and guild mates on several occasions, and he always pays back his debts. Downer's brother Aristide claims Downer is a "jerk", but then, Aristide is more of a typical drow (read: selfish and cruel) and his viewpoint is questionable. By the end of Fool's Errand, Downer's status has been firmly updated to Anti-Hero.
Subverted with Jack from Fables and its spin-off ''Jack of Fables." He starts out like this but get to know him long enough and like the tpb character introductions state he is the "lovable rogue" without the "lovable" part.
From the same series is Reynard the Fox, who appears as one, who seems to have a self-serving agenda, but then genuinely appears to just want to help. He even points out that being self-serving and helping others are goals that complement each other.
The Black Fox, a Gentleman Thief foe of Spider-Man, has this vibe going for him. So much so that Spider-Man actually lets him escape from their first few encounters because he just can't bring himself to send the Fox to jail.
Gambit is made of this trope. He's a very charming thief.
A Far Green Country. Elden is a deserter and a thief. Also, Durus and Surad are thieves. The story presents all three characters as protagonists: Elden became a thief for his own survival, and Durus and Surad become his allies.
The Artful Dodger, in most film and stage versions. In the original book... not so much....
Phil Moscowitz, the hero of the Woody Allen comedy Whats Up Tiger Lily?, who identifies himself as one when giving his name and occupation and whose lecherous behavior certainly fits the type.
Daniel Dravot (Sean Connery) and Peachy Carnehan (Michael Caine) from The Man Who Would be King. They're unscrupulous con men who set out to use modern weaponry and tactics to manipulate a small nation into appointing them kings, with the intent of making off with hoards of treasure, but for most of the film you can't help but root for them. This is very much a matter of Adaptation Distillation, since the original characters in the Kipling story are not particularly attractive, and Kipling doesn't pretend they are
Han Solo from Star Wars. He seems to be so lovable that all the pretty rotten things he has done seem so justifiable that they don't seem to sink in.
Particularly in the Han Solo trilogy, but also in many other EU books, he has conned a number of people, smuggled what is basically the hardest spice (SW equivalent of drugs) available, stolen, forged government documents, entered Imperial services under a false ID, faked his own death, cheated at games of chance, betrayed several employers, led a picket ship on a chase that resulted in its complete destruction, bribed an Imperial officer, freed slaves (morally good, but technically illegal), led a raid on a former employer's base, resisted arrest a whole lot of times, kidnapped Leia, and killed numerous people (though all of them were at least directly or indirectly trying to kill him at the time). In some instances, these acts were justifiable by being morally good or because he didn't have any sort of choice, but in other cases they were purely selfish acts to get what he wanted.
Essentially, the only two lines he consistently has shown is an unwillingness to kill anyone in cold blood and a refusal to take part a direct part in any type of slavery operation (he would work for slavers in other matters though).
Talon Karrde has been said by his creator to be based off of what Han Solo might have become in the years since the films, if he hadn't fallen for Leia. Karrde developed from there — it's hard to imagine Solo running a large and well-organized smuggling/information brokering group — but the basic idea is the same. He's Not in This for Your Revolution, he has no love for the Empire but doesn't see the profit or point in open resistance, and he does have a sense of honor.
The audiobook version of Heir to the Empire even felt the need to give him a Spanish accent.
Captain Jack Sparrow, from the Pirates of the Caribbean movies, is a mix of this and Magnificent Bastard. He has his own peculiar code of honor and is generally a protagonist, but is highly pragmatic and values his own skin over everyone else's.
Cdre Norrington: "You are without a doubt, the worst pirate I've ever heard of."
Plunkett And Macleane's titular Macleane definitely fits the bill in spite of his thieving and gambling ways.
Frank Skeffington, the crooked big-city machine politician, is undoubtedly one of these in the movie version of The Last Hurrah; he is ferociously loyal and would never desert a friend, and if he sometimes uses money or offices to secure political favors, he only does it to help out his constituents. He is slightly more overtly sympathetic in the film than in the book (see "Literature" section below).
Rodney Skinner, in The League of Extraordinary Gentlemen. A cheerfully self-acknowledged Gentleman Thief, who stole the invisibility serum so that he could be the greatest thief in the world, he arguably emerges as the most loveable character in the whole movie. Bonus points for being the Reverse Mole and also for winning over fans of the graphic novel who were disgusted by his predecessor, original invisible man Hawley Griffin.
Danny Ocean & Friends of Oceans Eleven. They're all charismatic in their own way, and everyone hates Asshole Victim Terry Benedict anyway.
"Professor" Harold Hill, of The Music Man, is this, with a heavy emphasis on the Lovable part (since he's also The Charmer).
Private Hook in Zulu. Note artistic liberty here; the historical Private Hook was no malingerer, not in any way a disciplinary problem, and fought even more bravely in the battle than the film portrays him as doing. His surviving relatives walked out of the premiere when they saw how he'd been portrayed.
Hachi in Onibaba, though he's a pretty dark example, he's about as close as the movie gets to sympathetic.
Brad Pitt typically plays this type of character, such as Mr and Mrs Smith.
Stephen Bloom in "The Brothers Bloom". He's a con man who has no problems stealing money, blowing things up, and even occasionally being violent. He drinks, smokes, and swears. However, unless you try to hurt someone he cares about, he doesn't wish real harm on anyone. Stephen spends most of his life with one goal: taking care of the little brother he loves. In fact, the entire movie is a plot of Stephen's to find a way to make his brother happy.
Frank Abagnale of Catch Me If You Can (winningly played by Leonardo DiCaprio). He's a very clever young man who successfully passes for a lawyer, doctor, and airline pilot, whilst committing millions of dollars worth of check fraud. But he only does this because he sees no other prospects for himself; what he longs for most is a stable family. Pursuing FBI agent Carl Hanratty (Tom Hanks) comes to realize this, so arranges for Frank to eventually achieve a happy ending. This story has some overlap with Real Life.
Moist von Lipwig is one of these turned Boxed Crook. There's a bit of Deconstruction on the idea that he's only conned big businesses and people who deserved it, and never hurt anyone. Mr Pump reckons that, if you add up the amount of harm he's done, it's equivalent to killing 2.338 people, and this really gets brought home when it turns out his girlfriend lost her job when he defrauded the bank she worked for.
The new miniseries subverts the expectations even more harshly; he apparently drove at least two people to suicide, and one innocent to prison, since he failed to realize that banks themselves would never admit mistakes on their part. It also multiplies the indirect deaths he's caused by a factor of (nearly) ten to 22.8.
Night Watch's Carcer Dun is a subversion; Vimes notes that he certainly looks and acts like one of your standard cheeky-yet-lovable-rascal types, but if you look closer you'll realise what an insane and unrepentant monster he is.
Reacher Gilt is another subversion, a pretty nasty piece of work who charms people with his florid, pseudo-pirate style - he even has a parrot which squawks "twelve and a half percent" (work it out... )
George Cooper, King of Thieves, from the Tortall books. His title is actually "The Rogue", and he basically runs the thieves' organization throughout the kingdom. (He later becomes the realm's spymaster.)
Also Rosto the Piper and his friends in the Provost's Dog books. He actually builds George's future home base, the Dancing Dove Inn.
Frank Skeffington in The Last Hurrah is a crooked big-city machine politician who is nonetheless beloved by his constituents (and not because he is fooling them- they know how he works, and they don't care). He may hand out offices and money as a way of buying political power, but he is ferociously loyal and would never desert a friend. Still, his portrayal is a little more overtly sympathetic in the Film than in the novel, which is slightly more ambivalent about him and his legacy.
The Nightrunner series is centered around spies and thieves.
The Hobbit: Bilbo Baggins is hired to be one of these, and manages to become one after obtaining the ring.
Gonff, the Mousethief, from the Redwall novel "Mossflower" is decidedly one of these.
Fred and George Weasley from the Harry Potter books. While in school they take a positive delight in breaking rules, including a couple of actual wizarding laws, and messing with people but always remain on the 'good' side of things. After leaving school they open an amazingly successful joke shop.
The Marauders would be another, at least when they were young, having actually broken the law by not registering to become animagi, and being a bit jerkier.
Adventurer, mercenary, pirate, counterfeiter and all-around adventurer "Half Cocked" (you don't want to know how he got that nickname) Jack Shaftoe, King of the Vagabonds and hero? of Neal Stephenson's The Baroque Cycle
Jonathan Small, opponent of Sherlock Holmes in "Sign of the Four" has committed various acts of murder and robbery, which he tells of in detail - and still has much of the reader's sympathy. He has a strong loyalty to his three co-conspirators; also, much of his story takes place in a quite brutal penal colony - and of course, in this situation the reader tends to side with the prisoner against the guards.
Like the Discworld example above, almost deconstructed in Chris Wooding's Ketty Jay series with Darian Frey, the main protagonist. He's a petty crook, and while he's certainly charming, has yet to cross the Moral Event Horizon, and learned loyalty to his crew, he is also deeply selfish and the author never lets us forget his flaws for long. In his first appearance he allows an enemy to shoot his friend and shipmate rather than lose his ship; in the first scene of the second book, he and his crew are found robbing an orphanage. Yet, they remain sympathetic. That takes skill.
Fisk from the Knight andRogueSeries is this for the first two books, though by the third constant close quarters with Michael seems to have gotten him to behave a little more within the law.
Dirk Slipstream in the Doctor Who novel Night of the Humans claims to be this. However, it turns out he's a mass murderer and an escaped convict out to settle a score with the Doctor and obtain a powerful artifact. He still talks like a British rogue (e.g. "sorry, ol' chap").
Ragnar Danneskjöld of Atlas Shrugged is a pirate who steals from relief ships bound for famine-struck countries. He, quite literally, steals food from starving children. (He keeps most of the profits, too.) It is implied, by the narrator that most of those relief goods never would have reached those starving children anyway. Nevertheless, he is presented as a charming hero.
Count Vega from Wereworld. A pirate, exile, and a lady killer who has a crush on Whitley.
Ilmar the Slick in Sergey Lukyanenko's Seekers of the Sky duology is a thief, a grave robber, and a murderer (although in this world's mythology he hasn't yet committed the "mortal sin" of killing a dozen). He's also a devout follower of one of the two Churches of this world (the one more concerned with redemption and forgiveness than punishment) and will often donate sacred texts found in abandoned temples to the Church. Unlike a typical rogue, Ilmar isn't shown to be particularly charming. His fling with a female pilot (who's also a countess) happens after he kidnaps her and forces her to fly him to the mainland. They crash, and she ends up having Glad-to-Be-Alive Sex with him, while he can't even move.
Jeff Raven of The Tower and the Hive series. A Prime-level "Wild Talent" (a psychic-powered human with no formal training), who swoops in and claims the heart of The Rowan (the strongest Prime around) with nothing more than confidence and mental rapport.
Jean Valjean from Les Misérables, the book's primary protagonist, Atoner, and Messiah. He's a convict who spent years in prison for stealing a loaf of bread to feed his sister's starving family, with more added to his sentence due repeated attempts to escape - making it a total of 19 years. He then spends the rest of the story trying to make the best of his life by being an honest man.
Bret Maverick, from the aptly named western Maverick. Most often Bret is forced to break the law by escaping jail for crimes he's framed of, or commits crimes as part of schemes and cons to outwit those they have wronged him, (stolen his winnings), or his loved ones.
Vila Restal from Blake's 7. Not to mention being a card-carrying coward.
Captain Malcolm Reynolds from Firefly and Serenity.
Jayne fits the type, even if it's only the audience that finds him lovable. He's like Mal, but without the (semi-)moral compass. Or the smarts ... though he does look cunning in that hat.note "That hat makes you look ridiculous."
The main characters from Hustle, a team of con artists who only con those who deserve it.
On the other hand the original series did it very well with the immortal and immoral Harry Mudd, as well as the somewhat more benevolent Cyrano Jones.
ST:TNG also had a supporting character named Vash, a female version of this trope who romanced Picard for a short time. For bonus irony points, Q casts her as Maid Marion in a Robin Hood fantasy.
Star Trek: Deep Space Nine: Quark is one of these most of the time almost to the point of being a Gentleman Thief. This makes him the first exemplar of the virtues of Ferengi. Its telling that Quark is noticeably uncomfortable when he turns to arms dealing to stay afloat and the people who liked him up to that point are disappointed in him. He also typically abhors violence.
Hellooo, he's Captain Jack Harkness of Torchwood fame, pleased to make your acquaintance.
The Doctor from Doctor Who stole his TARDIS, fled his home planet, disrespects most forms of authority and is a very loveable guy. Especially Four in the classic series and Ten and Eleven in the new series.
River Song is a rare female example of this trope. She's a time-travelling archaeologist, convicted murderer, thief and still saves the universe every now and then with the Doctor.
A (less heroic than the above) example from the classic series was Sabalom Glitz, a charming conman who showed up in a few episodes and became a friendly acquaintance of The Doctor. His character was so enjoyable that episodes featuring him tended to gloss over things like him selling his mutinous crew into slavery.
Sawyer from LOST, a highly popular character despite being a conman and murderer.
In season 5, he develops from one into a snarky but otherwise perfectly heroic character. The actor has said that Juliet's death will push him into this territory again in season 6... except drop the "loveable".
Claude Greengrass in the British period police soap Heartbeat. Lampshaded when a character calls Greengrass a rogue and he responds "Yes, but I'm loveable".
Also later Peggy Armstrong, who began as an Unlovable Rogue but was subsequently softened. In between there was Vernon Scripps, who is often considered this, but stayed on the right side of the law.
Jack and Stan from On The Buses. Not criminals, just terminally lazy.
Neal, the main character of White Collar personifies this trope.
Omar, from the HBO series, The Wire definitely falls under this category. He makes his living ripping off drug dealers and is constantly killing people. But he has a moral code of "all in the game" and he is just too loveable for the audience not to, well, love.
Neil from The Librarians sees himself as a loveable rogue. No one else does.
All of the members of The A-Team are this since the bad guys are so one-dimensionally horrible, but Face probably fits here the most since he's the slick and charming ladies' man (and Con Man). The team also fits as a group of Anti-Heroes.
Starbuck from the original Battlestar Galactica. Added bonus when played by Dirk Benedict, who was also Face.
Darien Fawkes in The Invisible Man. He's a notorious thief who only got caught last time because he tried to revive an old man he thought was having a heart attack (instead, he got convicted for attempted rape). His brother, an accomplished scientist, gets him out of prison to be the guinea pig for a top-secret project. After Darien gets the quicksilver gland, he can now become invisible at will. A dream come true for a thief. However, he needs regular injections of a counteragent that prevents him from going insane from quicksilver overdose, a deliberate flaw in the gland. Despite now working for a secret government agency, Darien still has plenty of roguish qualities, who loves to use his new ability to sneak into places he shouldn't (like spy on a guard and a nurse getting it on). However, in the series finale, the flaw in the gland is finally fixed, allowing him to be free from the Agency. The first thing he does is rob a place, only to leave the money on the sidewalk when he realizes he's not the same guy anymore.
Lutin, from The Legend Of Dick And Dom, is introduced in the opening credit voiceover as the heroes' thieving servant. Saves the quest several times with heists, capers and jailbreaks, as well as routinely sabotaging opponents and lifting small items; she's a classic cheeky, sarcastic rogue.
Dennis Stanton on Murder, She Wrote. A jewel thief who crossed Jessica Fletcher's path several times. (He ended up using his skills for legal purposes as an insurance investigator.)
Danny from Redfern Now is a shoplifter who becomes inadvertently involved in a hit-and-run—when he calls an ambulance in the latter case it begins his Character Development that puts the "lovable" in his character.
The late Eddie Guerrero was well known for his "Lie, Cheat, and Steal" lifestyle. But he was so damn charming, he'd usually get away with it, all the while stealing the audience's hearts.
Former French President Jacques Chirac is portrayed this way in the satirical fake news show with puppets Les Guignols de l'info, being shown to be a shameless liar (he even had another identity as Super Menteur, i.e. "Super Liar") while still remaining highly likable. It's thought this may have actually helped (the real) Jacques Chirac get re-elected.
There's a good chance that any given Thief/Rogue, Bard, or Swashbuckler you meet in a game of Dungeons & Dragons is this kind of character.
An old maxim of roleplaying states that "A thief or rogue characer will never be morally centrist. He will either be a good-natured chap who steals from people who deserve it and is the subject of much affection, or he will be a complete sociopath".
There's an even better chance they won't be, but will pretend they are.
Luis Sera from Resident Evil 4. A charismatic womanizer with a good heart working for the wrong side.
Locke the treasure hunter, from Final Fantasy VI is pretty much the definition of this trope, though he drifts into being less of a rogue and more of a hero as the game progresses.
Practically 25% of the world's population in Skies of Arcadia is made up of these. Naturally, this includes all the playable characters.
Balthier from Final Fantasy XII. Considering how much Final Fantasy XII seems to be inspired by Star Wars, he's almost certainly inspired by Han Solo.
If Robin Hood is a Loveable Rogue, then definitely we have to include Yoshimitsu of SoulCalibur and Tekken. In both games, he steals from rich people and gives to the poor, much like Robin Hood. Most people love him, even if he's not really important to either storyline, but everyone loves him only because he's just so damn awesome. It helps that he can use his sword as a pogo stick. And as a helicopter.
Hawkeye from Seiken Densetsu 3, who seems to be modeled off of Robin Hood.
The two characters in Ace Attorney who get a Karma Houdini fall under this category. For Phantom Thief Ron De Lite it's because he's so darn adorable and for Shelly de Killer it's because he's such a classy assassin.
And Kay Faraday, even though she doesn't technically steal anything. Except the truth!
Gaius, from Awakening, is first seen with a band of assassins with designs on killing the Exalt, having been led to believe they were just there to rob the place. He's... upset when he finds out the truth, and joins the party at the prospect of free candy as well as being in more savory company.
The Prince in Prince of Persia (2008) seems to be this, considering how the developers have stated that he's inspired by Harrison Ford's characters. Although the ending also has a VERY serious moment that might be crossing the Moral Event Horizon.
Nick from Left 4 Dead 2 has a somewhat shady (and probably violent) criminal past, and he starts out with a lone wolf-style attitude, but because of the circumstances he's in, as the game progresses, he's slowly forced to shed that attitude, and learns to trust and respect his teammates (well, respect MOST of them) and almost grows close to them, through whatever they go through.
It also helps that he's the character providing most of the game's Deadpan Snarker. He bounces some of the best lines off of Ellis because of this.
Nathan Drake's interactions with his crew in the Uncharted series makes him an lovable and entertaining rogue. He also tends to operate at least somewhat outside the law (such as being forced to get into an explosive gunfight with pirates in the first game's intro due to operating without a permit), and Uncharted 2 opens with him engaging in a museum break-in.
Yoshimo also works hard to project this image, although there are moments where it's a little off. From all indications he was 100% this trope prior to selling his life and soul to Irenicus.
Saemon Havarian probably works as this as well, if not for the fact that half of the time the one he's screwing over is you. He seems to hold no ill will towards you or anyone despite throwing you to the wolves repeatedly to save his own skin (and he does seem to have an interest in defeating the Big Bad as long as he's not in the direct line of fire), and you have the option of having CHARNAME reciprocate. After about the third time he backstabs you the dialogue offers the line that it's basically just Saemon being Saemon.
Neeshka from Neverwinter Nights 2. She is a sort of a tiefling reincarnation of Imoen. Safiya's familiar in Neverwinter Nights 2: Mask Of The Betrayer may count as well.
Chosokabe Motochika from Sengoku Basara is a kleptomaniac pirate known as the "Demon of the Western Sea" who crushes people's skulls with a giant anchor. However, once you get past this he's actually a fairly honest, charming, and good-hearted guy who values things like friendship and keeping promises, and overall one of the most honourable characters around.
Speaking of Eidos, Gex was reportedly supposed to be this, as revealed in the interview with the creator at the end of the Enter The Gecko Strategy Guide.
And for that matter, don't forget Garrett from the Thief series.
Rikku from Final Fantasy X. Sure, she's a thief who comes from a group of people who are considered heathens, and even kidnaps Yuna at one point, but she's also a sweet, lovable Genki Girl who's always ready to brighten up the mood.
Sly Cooper from the Sly Cooper games definitely falls under this category, along with the rest of the Cooper Gang.
Isabela from Dragon Age II sits here with a drink and a few knives most of the time, if only because of her easygoing nature and the fact that the loss of her ship has forced her into a lack of pirating recently.It can be subverted when she abandons Hawke and Kirkwall to the Qunari at the climax of Act II. If the player has her at at least 50 friendship/rivalry though, she'll come back. There's also the fact that she lost her ship in the first place because she refused to carry a shipment of slaves.
Zevran and Varric also count. One of them is a charming assassin with some degree of conscience, the other is a witty information man.
Ozan, one of the Signature Heroes of RuneScape, seems to fit this category well. He happens to be a thief and a liar with an inflated ego... Yet his friendly, fun and charming personality makes him likable despite this. Oh, and he is a hero (if the term Signature Heroes wasn't enough of a clue).
The Legend of Zelda: Skyward Sword introduced the Mogmas, a race of tunnel dwellers who are mostly seen plotting to steal ancient treasure from the local temples. Despite being thieves they always repay debts, and their kindness and inclination to help Link save Zelda make them very lovable.
Raven from Tales of Vesperia, who, despite being a bit of a pervert and working a selfish agenda, also happens to be a genuinely good guy and the comic relief character.
Lyndon from Diablo III, despite the setting, falls squarely into this category, much thanks to his charming (and humorous) personality. He does have some noble motivations at least—one of his own thefts caused his brother to be imprisoned, and Lyndon is working to get him freed.
The Spy from Team Fortress 2 considers himself this, and is one when on your team. On the enemy team, he's a sadistic psychopath.
In later video games, the crew of Saints Row makes a point of deliberately branding themselves as this trope as they become famous.
And back in the main party, Haley Starshine probably qualifies, even though we almost never see her actually break any laws (at least, in the strip itself).
We see her doing a sneaky burglary and theft in the prequel On the Origin of PCs, and likewise in this online comic strip. Suffice to say, in Dungeons & Dragons the Thief or Rogue has been a character class from the beginning, and a life of crime does not mean a thief character is automatically considered evil in alignment, he just cannot be lawful.
At least in the 3.5 and 4th editions, even that was dropped when rogues were generalized towards "sneaky and talented one", including characters like spies or assassins with codes of honour.
In Freefall Captain Sam Starfall is not only a Loveable Rogue, he apparently comes from an entire race of them
UU: a rogUe is a passive class. yoU see, there are passive (+) and active (-) classes. some more strongly passive or active than others.
UU: the +/- distinction can mean many things, bUt coUld be qUite roUghly sUmmed Up in this way: active classes exploit their aspect to benefit themselves, while passive classes allow their aspect to benefit others.
UU: classes always come in +/- pairs, with significant disparity between them.
UU: while a rogUe is passive, a thief woUld be its far more active coUnterpart.
TG: so basically
TG: a thief is like the asshole class
TG: the player who says step off shits mine suckas
TG: a rogue
TG: is bascially robin hood
Captain Heinrich Lehmann-Willenbrock in Hitler Rants. In Das Boot, he was a Tragic Hero caught up in a war he did not understand. In the U-Boat Parodies, he's a loveable, manipulative rogue who always manages to remain one step ahead of Hitler, and almost always finds ways to benefit from the latter's misery.
Rattrap from Beast Wars. At one point Optimus Primal is presumed dead during the course of one night. During that time Rattrap takes it upon himself to take over his (much nicer) quarters and replace everything with his own stuff. When he is called out on it, his response is basically "Hey, come on. What do you expect?"
Puck from Gargoyles most definitely qualifies. "Sunny disposition and always kind to animals" indeed.
Daffy Duck of Looney Tunes fame, under Robert McKimson's direction was evolved into a compromise of both his former and latter forms, often acting as a con artist or door to door salesman. In tradition with this trope, his luck was often karma based, when trying to swindle protagonists such as Bugs Bunny and Porky Pig he was usually foiled, when trying to make money out of antagonists such as Elmer Fudd and the Tazmanian Devil however, Daffy would often make a profit.
Shaun the Sheep in his spin off series. His schemes often involve screwing the Farmer or Bitzer in some way, but he has no harmful intent and occasionally tries to do nice things for them to compensate. Usually the rest of the flock get in on this too.
Teen Titans has Red X, who is not only entertainingly witty during combat, but also manages to completely dominate all five Titans at once. He also remarks that he doesn't steal for any sort of incomprehensibly psychopathic reason; he's just doing it all for the fun. To add to this status, he even saves the heroes' lives and helps save the city before escaping.
Top Cat and his gang of alley cats are either con artists or Zany Schemers, but have altruistic qualities and a ton of charisma to boot.
Also Yogi Bear of the same team. He's obsessed with stealing 'pic-a-nic baskets' from campers and often winding up Ranger Smith in the process, but he's a friendly easy going guy who is repentant when his stunts cause significant problems in the park. In most interpretations he is not portrayed as a thief he becomes an outright protagonist solving mysteries or helping friends.