The male version of the Classy Cat-Burglar may lack the cat jokes and themes, but he makes up for it with roguish good looks coupled with a breeding and style that manifests as a suave and debonair manner. He's usually a charmer, too — think James Bond without the government authorization. Cary Grant used to play this type of character frequently.
He steals for the challenge/pleasure of the job and generally avoids violence while restricting his targets to those who can afford the loss. More importantly for plots, the character will often go out of their way to stop more serious crimes - especially with lives at stake - either on their own or with the help of the police. As such they often adhere to Thou Shalt Not Kill and/or are Technical Pacifists. Murdering your target or stealing from them at gun point is not very gentlemanly. It's not uncommon for the GT to give at least a part of the goods he steals to the poor, often while very cynically commenting on social injustice and how the rich surely got their wealth with dirty methods, so it's only fair to steal from them and then give to those who need it.
Like the Classy Cat-Burglar, the Gentleman Thief usually regards the police with a certain amount of disdain and condescension, and frequently leaves behind "calling cards" announcing who performed the crime; especially confident versions may announce their targets in advance to ensure a challenge. With a Worthy Opponent such as a Sympathetic Inspector Antagonist chasing him, they may have a less adversarial relationship, verging at times on friendship such as leaving Big Bad crooks behind for him to take the credit arresting (and when the opponent is of the opposite gender, fraught with UST of the Dating Catwoman variety). They're usually a Badass in a Nice Suit, occasionally doing the Tuxedo and Martini look. As he may not enjoy actual risks, the Gentleman Thief may decide that gambling is beneath him and cheat instead. Expect him to do so with sophistication. If he does gamble, expect him to be almost supernaturally lucky, or a tournament-grade player without peers. In many cases, they steal because they can and for the thrill, not out of an actual monetary need (since they are often rich) — though it may be a way to stave off Rich Boredom. This is also why they will never give up thievery for simple gambling.
They do exist in Real Life, yet their most usual technique is not stealing per se, but more like conning the victim.
Sometimes overlaps with Phantom Thief or Karmic Thief. See also Scoundrel Code.
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Ijyuin Akira, the Man of Twenty Faces, in CLAMP School Detectives: a young gentleman thief, he steals according to the direction of his two mothers. This character is based on Japanese mystery author Edogawa Ranpo's "Fiend With Twenty Face".
This character also reappears as "Twenty Faces" in The Daughter of Twenty Faces, who, among other things, steals national treasures that have been mislocated due to war to return them to their rightful place.
Lupin III, Lupin's grandson, acts like this on the surface, but the breeding isn't always present. He always ends up revealing his awkward/goofy side, and, when it comes to women, he acts more like a drooling pervert than a smooth Casanova. Can vary based on the writer, though.
The titular character in From Eroica with Love; the title is actually what he leaves on his calling cards.
Cobra from Space Adventure Cobra is a gentleman thief in a Space Opera setting. Despite being one of the most wanted criminals of the galaxy, he ends up helping the Space Police and battling the Space Mafia more often than not.
Dark from D.N.Angel is called a Phantom Thief, but he's definitely an example of a Gentleman Thief as well. He steals only works of art, sends a warning letter before every steal, and definitely thinks less of the cops. It's also later revealed that he has a reason for why he steals.
From Detective Conan - the illustrious Magic Kaito (if he isn't too perverted too count). However, his exploits are surprisingly mundane, using disguises to escape instead of stylishly flying with his cape/glider. At one point, he even resorts to swimming all the way from a ship to the harbor to escape.
And on a related note, we have the Lupin III vs. Detective Conan anime special where Conan chases after Lupin and Co. and they have to team up to rescue Ran, who's been caught in a massive conspiracy.
Mamoru "Tuxedo Kamen" Chiba in the manga and Live Action version of Sailor Moon, though only to find the Silver Crystal so he can recover his long-lost memories, and he stops when they do find it and becomes solely a superhero. Sailor Moon even comments "He's just like Lupin the Thief! He's hot!" when she first sees him in the Manga. It causes severe friction between him and the Senshi in the Live Action version.
Lunlun meets one of these in the Egypt episode of Hana Noko Lunlun, a charming and stylish middle-aged man who plans to commit quite the robbery of Ancient Egyptian jewels/relics/etc. and tries to use her as his Unwitting Pawn. Uncommonly for this type of character, he is captured by his Inspector Javert - but by that time Lunlun's innocence and kindness has touched his heart, and is last seen keeping flowers in his cellar.
The Phantom Blot of the 40s, a Disney villain.
Gambit, from X-Men: charms the ladies while taking their pocketbooks.
Fantômas, going so far as to wear a top hat, opera cape, and cane while performing his second-story jobs. (He eventually stopped doing that, however.)
In the first issue of Uncanny X-Force, he raids the Tower of London on a wager with Wolverine and, upon losing (Logan beat him to the vault), agrees to pay Logan with a case of cognac, worth "two million dollars a bottle". It's not about the money, but rather, it's simply "his poison".
This was heavily implied to be a bet between the two where the loser had to buy a case of alcohol for the winner.
The elderly criminal the Black Fox. (His schemes usually revolved around making a big score so he could retire from crime.)
There's also Walter Hardy, father of the Black Cat. Unfortunately, he's something of a subversion in that he keeps retiring because he causes more harm than he intends to. In regular comics continuity and the 90s cartoon, he's tricked into working for Nazis and nearly gets them a Super Soldier formula. In The Spectacular Spider-Man, he became The Atoner after killing Uncle Ben in a moment of weakness.
Marvel also has Shen Kuei, aka "The Cat" (he even has a tattoo of a cat on his chest), who is both this trope and a rare male example of the Classy Cat-Burglar at times. He's not only a skilled thief, but he also has martial arts skills that rival his arch enemies, Shang-Chi and Iron Fist.
Deconstructive Parody in the Viz strip "Raffles the Gentleman Thug", in which the titular character is a well-spoken, aristocratic Jerk Ass who goes around beating people up for no reason.
Subverted with Hunter Rose in Grendel, who has all the usual hallmarks but is actually a ruthless organised-crime boss who kills huge numbers of sometimes completely innocent people.
The Rogue from The Maze Agency (who never actually appears on stage). His Calling Card is a note informing his victims that their stolen paintings have been selected for his 'Rogue's Gallery' and 'signed' with a cartoon figure (a la The Saint's haloed stick figure).
The DC anti-villain/anti-hero The Shade has been presented this way since the 1994 series, Starman, though he hasn't done much thieving recently.
Niven also plays Colonel Matthews, the titular character of The Brain, where he, two petty crooks, and the mafia attempt to hijack a train transporting the NATO millions to the new NATO headquarters. Hilarity ensues.
Pierce Brosnan plays a millionaire trying to be a Gentleman Thief in The Thomas Crown Affair. "It's just a game, love; it's just a game."
Complete with a literal calling card: a pencil with the name of his firm left plainly at the scene of the final caper!
And, of course, the original 1968 film starring Steve McQueen.
Sean Connery's character in Entrapment is just the bearded Scottish version of Pierce Brosnan's Irish Thomas Crown. Except Connery shares his screen time with a Classy Cat-Burglar and the infamous Laser Hallway.
Robert De Niro's character in Heat, Neil McCauley, is a somewhat more realistic version of the Gentleman Thief.
Basically every protagonist in Ocean's 11, Ocean's 12, and Ocean's 13, as well as the antagonist "Night Fox" Toulour, though to a lesser extent.
Nick Wells (Robert De Niro) in The Score. He even owns a jazz club.
Frank of Robot And Frank is not particularly classy or refined, but still shows aspects of this archetype, such as his meticulous research before each job and his insistence that only "those insurance company crooks" will get hurt from his heists.
Fantômas is a literary and cinematic Gentleman Thief from France. He's also kind of a psycho-murderer as well. Crazy name, crazy guy.
Robin Hood, in his usual classic portrayals, robs from the rich and gives to the poor. In some versions, he is a former Noble, making him more literally a Gentleman Thief.
Raffles: a character who has been around in literary form since the 1890s. Invented by E. W. Hornung, who meant him to be a subversion of the trope: definitely not a nice guy, and stealing for profit rather than for fun or altruism. (See further discussion under Depraved Homosexual.) It was no use, though; Hornung's readers saw Raffles as glamorous anyway, and later incarnations of the character invariably make him into a hero.
See the other Wiki for a list of works featuring Raffles. Also recently appeared as a minor character in the webcomic Scary-Go-Round.
The difference between Raffles as created by Hornung, and Raffles as developed by others was parodied by Jon L. Breen in "Ruffles versus Ruffles", where the no-good crook and the heroic adventurer are brothers: A.J. Ruffles and R.J. Ruffles.
Arsène Lupin, titular thief of the series of short stories and books written by Maurice Leblanc between 1905 and 1939, and five additional volumes written by Boileau-Narcejac in the 1970s. This Gentleman Thief moonlights as a detective. He was the precursor of Arsène Lupin III, and is pretty much the Trope Namer, as the first collection of short stories on the character is called Arsène Lupin: Gentleman Cambrioleur (Arsène Lupin: Gentleman Burglar). He's also the Trope Codifier, exhibiting many of the tropes associated with this trope and Phantom Thief: Calling Cards, being a Master of Disguise, announcing his crimes ahead of time, fighting evil criminals and displaying a general romantic attitude.
Flambeau is a clever, strong, joking, and very tall jewel thief of the Father Brown series by G. K. Chesterton. His name means "torch" in French. He liked to use paradoxical disguises (as in "The Queer Feet"). After several encounters with Father Brown, he gave up crime and reformed.
Subverted to pieces in the essay Memoirs of a Private Detective by Dashiell Hammett:
Second only to Doctor Jekyll and Mr. Hyde is Raffles in the affections of the daily press. The phrase "gentleman crook" is used on the slightest provocation. A composite portrait of the gentry upon whom the newspapers have bestowed this title would show a laudanum-drinker, with a large rhinestone-horseshoe aglow in the soiled bosom of his shirt below a bow-tie, leering at his victim, and saying: "Now don't get scared, lady, I ain't gonna crack you on the bean. I ain't a rough-neck!"
The Saint, AKA Simon Templar, was such a Gentleman Thief in the original stories (and also mixed race as well, unusual in those days) that the TV series cleaned him up a lot, though not entirely.
The Saint doesn't quite fit the trope, in that he was in the habit of murdering criminals as well as taking their money. On one occasion, he tied the villains of the story up in an abandoned house, to which he then set fire, leaving them to burn alive. Granted, they were going to do the same to him and his cohorts, but still, not entirely gentlemanly behaviour.
Nobby Cranton from the Lord Peter Wimsey novel The Nine Tailors pretends to be a Gentleman Thief. The only impediment is that he isn't a gentleman.
Philip Collin, aka Professor Pelotard, from the various books and short-stories by Frank Heller. One thing that helps make Collin into one of the more memorable gentleman thieves is the fact that his first crimes are the same as his creator's, who, before becoming an author, was a swindler who went into a self-imposed exile in order to escape the Swedish police.
Nick Velvet (from a series of short stories by Edward D Hoch) is a professional thief for hire, with a peculiar specialty: for a flat fee, he steals only objects of negligible apparent value. Since his first appearance in Ellery Queen's Mystery Magazine in September 1966, he has stolen such things as an old spiderweb (which he was then obliged to replace), a day-old newspaper, and a used teabag. His original fee for a theft was $20,000. In 1980, he raised it to $25,000 at the urging of his long-time girlfriend Gloria (who met Nick in 1965 when he was burgling her New York apartment); in the 21st century, his fee has risen to $50,000. Unlike many fictional thieves, Nick usually works alone on his thefts — in fact, until 1979, Gloria believed that Nick worked for the U.S. government.
"Slippery" Jim diGriz, the protagonist of The Stainless Steel Rat. Living in a future where only a genius could ever make it as a crook, he considers himself a public benefactor by spicing up the lives of local police and keeping the money in circulation.
John Smythe Tregarth from Elizabeth Peters' Vicky Bliss series.
Silk, also known as Prince Kheldar, from the Belgariad and the Malloreon, is an excellent example of this. Of course, he is also a spy. And a successful entrepreneur to the point that he can get away with the Mallorean government being aware of him being this trope and a spy (well, an important and very good spy. All Drasnian merchants are assumed to be spies), simply by being so integral to their economy that it'd crash if he withdrew.
George Cooper of Song of the Lioness is King of the Thieves and keeps "court," which has rules that he follows. He's a Worthy Opponent to the Lord Provost and has no problem befriending a couple of pages.
Rosto the Piper in the Provost's Dog books is sometimes speculated to have been a Scanran noble or similar because he's clearly well-educated and considered to be a very sensible Rogue.
The Thieves Guild in Discworld is said to run special courses for Gentleman Thieves. It's one thing being robbed, but it's annoying to learn that your possessions were stolen by a man in a borrowed suit.
The Discworld Assassins' Guild has a large proportion of gentleman members; this is because the Guild runs one of the best schools on the Disc, specialist subjects aside, and many upperclass boys get their education there before going on to other careers. It's not all upperclass males, though; the school now has two all-girls houses, and offers scholarships to prospective students who are too poor to pay the fees but show potential to be really good at killing people.
Moist von Lipwig may have scammed people out of all their money, but he has never committed a violent crime. Plus, after the challenge of his new job wore off, he turned to breaking into his own building.
Rather deconstructed, for that matter: Mr. Pump points out that, despite Moist's rules and Gentleman nature, he's still killed 2.338 people.
Although in Men at Arms, at least Edward D'Eath seems to think there could be no such thing as a gentleman thief: "If he had trained as a Fool, he would have invented satire and made jokes about the Patrician. If he had trained as a Thief (of course, no gentleman would dream of being trained as a Thief) he would have broken into the palace and stolen something very valuable from the Patrician."
Seregil (and Alec) in Lynn Flewelling's Nightrunner books.
The titular character in the Montmorency series is an interesting twist on this. He is a gentleman and a thief, but not both at the same time at first. He often struggles about which one is his real self and ends up progressing from a common pickpocket to a spy for the British government, at which point he truly becomes a Gentleman Thief.
The series title of Scott Lynch's Gentleman Bastard (The Lies of Locke Lamora, Red Seas Under Red Skies) gives a nod to this trope and to the nature of the central protagonists.
Locke is pretty much a deconstruction of this trope: his deeds inspired the legend of the "Thorn of Camorr", who is a gentleman thief, but the real Locke Lamora will not hesitate to kick a few dogs to reach his goals, even if he still have his standards (after all, he is also a priest of the 13th), hence the bastard (singular) in the series title. Because of his intelligence and education, people may expect this of him, even knowing that he is a thief. He speculates about this at one point, after he punches out his elderly woman captor, who apparently never considered that he would do such a thing, to gain an antidote to her poisoning and escape.
Kelsier and his crew from Mistborn by Brandon Sanderson.
Breeze however is the culmination of this trope in the group. He lives the fine wines and finer suits, and is the most larcenous of the team, whereas the others are usually a little more hands on and prone to mingling with the skaa.
Jack Foley, an Elmore Leonard character (from Out of Sight and Road Dogs). While he worked as a bank robber, he made a point of never using a gun while robbing more banks than anyone else in the FBI databanks. In the film version of Out of Sight, we get to see him in action, using only the suggestion of violence to rob a bank teller: he even talks politely with the stressed-out girl during the whole ordeal, to the point where she reflexively wishes him a good day when he leaves. It's only when he's dealing with genuine thugs that Foley gets violent.
In the follow-up novel, Road Dogs, an FBI agent desperate to arrest Foley is only obsessed with the ex-con because he's worried that the media will some day find out about Foley's story and turn him into a Gentleman Thief anti-hero.
Eli Monpress of The Spirit Thief is this, and also a wizard. His 'light' (it's hard to explain, you have to see it, says all the spirits) makes it so that most spirits will do as he asks without a servant or a slave bond (as the good guys and the bad guys use, respectively), letting him pull off blatantly impossible acts of wizardry. His goal in life is to increase his bounty to one million golden standards (an insane amount, quoted as being more money than exists in the world).
The In Death series: you can be sure that Roarke became this as he became an adult. He is as suave as they come and is certainly an expert at stealing.
Nicholas Valiarde (Donatien), a recurring character in Martha Wells's Ile-Rien series and the hero of the novel The Death of the Necromancer, is a master art thief from whom no wealthy collector's mansion is safe.
Panamon Creel from The Sword of Shannara Trilogy does an amazing impression of one of these, yet at the core he's far more of an Affably Evilhighwayman than he is one of these, and he knows it, putting on the act in an attempt at convincing himself that he hasn't wasted his life.
Quinn/Alex from Kay Hooper's Once a Thief and Always a Thief novels fits this to a T, though he prefers the term "cat burglar".
Dinotopia: Journey to Chandara has a highwayman who robs travelers of all their possessions and gives them all of their loot from the previous victim.
Jean le Flambeur from The Quantum Thief is a transhuman version of the character archetype, closely based on Arsène Lupin. He's a master thief in a day and age when upload-collectives rule the Solar System, and minds are a dominant currency.
Psmith, prone to occasional petty theft under the guise of "practical socialism", goes full-blown gentleman thief in his last installment, Leave It to Psmith, wherein he's hired to steal a diamond necklace. He's hindered by the fact that some rather less gentlemanly characters have been put onto the same job...
Dennis Stanton, a Recurring Character in Murder, She Wrote, was a Gentleman Thief in his first appearance, although in later appearances, he used his skills as an insurance investigator. He worked by three rules: he never steals from anyone who can't afford it, he never steals anything with sentimental value, and he makes sure that everything he steals is insured by the company who refused to pay for his late wife to have a lifesaving operation.
Jerry Fagin, an international jewel thief who made a single appearance in Cagney & Lacey solely to challenge Cagney to a duel of wits. His first action is to pull a heist and plant evidence all over the scene that points to the police department itself. When this becomes clear, Cagney immediately says, "Jerry Fagin! Nobody else would do this with such unmitigated . . . style!"
The Cat from the Funky Squad episode "Diamond's Are a Cat's Best Friend".
Remington Steele was this kind of character before taking over his role as a private investigator.
Hustle likes to play with this one. It's Albert's favourite character, despite him being a former cobbler. Mickey tends to be suave and debonair, as well. The others, not so much...
It Takes a Thief was about a second generation Gentleman Thief who was caught and given the choice of prison or helping the government. He chose helping the government. Inspired by, though not based upon, the 1955 Cary Grant motion picture To Catch a Thief (see above). Notable for starring Robert Wagner as the thief and Fred Astaire!!! as his father, who says at the start of every third season episode, "I've heard of stealing from the government, but stealing for the government?".
Subverted in the Psych episode, "Extradition: British Colombia." Pierre Despereaux seems to be one of these, but as it turns out it's actually an elaborate art-insurance scam: the owners let Desperaux steal the art (who then presumably sells it on the black market or perhaps keeps some of it himself), so the cash-strapped owners can collect the insurance money rather than having to sell the art themselves (which is rather embarrassing).
Played straight when he comes back in later episodes. He lives up to his previously fake legacy, and really is an amazing thief and escape artist.
While none of the main cast use this persona on Leverage, Archie Leach, played by Richard Chamberlain was Parker's mentor and appears to still be effective despite being retired.
Personas within the group are often traded; while they always are the Brains, Grifter, Hitter, Hacker, and Thief, the victims they are helping never know their roles, and the bad guys are sometimes made to believe that the roles have been switched. Sometimes that's the plan, and sometimes it's in response to a thrown curveball. Nathan, as the Brains, does play Gentleman Thief at times, as have the rest of of them every so often. Some of the best episodes come when the team are forced into roles that are far outside their comfort zone. (Parker or Hardison grifting is always gold, especially when they're attempting to be a Gentleman Thief/Classy Cat Burglar. And you know Eliot. He probably dated a female Gentleman Thief once. Or four times. Who knows?)
Neal Caffrey from White Collar presents himself like this but comes from a blue collar background and a large payout is his primary motivation for committing crimes. Flashbacks also show that if he is low on funds, he is not above doing basic street-level cons.
The Yatagarasu in Investigations, except the calling card is always sent after the theft...and what the Yatagarasu steals is the 'truth'. In other words, they (yes, they) uncover, steal, and deliver to the media incriminating information regarding people who otherwise can't be touched by the law, so that they'll actually be forced to pay for their crimes. The Yatagarasu's signature music is even CALLED Gentleman Thief.
Skye from Harvest Moon has - are you ready for this? - a "Maiden Chick Beam" that freezes women so that he can steal from them (of course, they're usually too busy swooning to stop him anyways). He also leaves a note before he steals, informing his targets of when he will arrive.
Dragon Age II has Varric, a Merchant-Prince. He's even introduced stopping a pickpocket from robbing Hawke, pinning the thief to the wall with a crossbow bolt, then while he's trapped casually offers some advice on how to rob people;
Varric: You know, I once knew a guy once who could take every coin out of your pockets just by smiling at you! But you, you don't have the style to work Hightown, let alone the Merchant's Guild! *Takes the coin back* You might want to find yourself a new line of work? *Punches him and pulls out the bolt* Off you go!
Hawke also falls into this role, at least in Act I where they're doing mercenary work and in the "Mark of the Assassin" DLC where he assists a beautiful assassin in stealing a priceless jewel. Well, not really, but they are trying to recover something valuable.
What Colm from Fire Emblem: The Sacred Stones grows into in his solo ending. If you get him to marry Neimi through supports, he gives it up to protect his new family.
The Purple Zephyr in Wario Master of Disguise. At least until Wario stole the magic cane which powered his transformations into his alter ego.
Jeremy Archer from Shadow Of The Templar. He uses non-lethal weapons to avoid killing people during his thefts, has sexual tension with Simon, the FBI agent chasing after him in the first novel (which stops being tension soon after), and acts as an occasional consultant for Simon's team on cases involving more dangerous criminals.
Kind of subverted in that, while he's extremely charming, any time he charms a woman, he does it with tongue firmly in cheek. It's implied that basically everyone knows he's gay (the team doesn't know because Jeremy doesn't want to mess up Simon's life).
According to Word of God, he's bisexual with a preference toward men.
The one-shot character Malloy from The Simpsons. After being caught at the end of the episode, he graciously returns the items he has stolen — immediately followed by tricking the entire town of Springfield into searching for his buried stash while he escapes their jail.
Barack Obama, John McCain, and the rest of the thief club in the South Park episode "About Last Night". Trey and Matt mention that Ocean's Eleven was their inspiration for their theft plot, so that helps.
Red X from Teen Titans. He also has a bit of a Worthy Opponent relationship with Robin that occasionally delves into Friendly Enemy at certain points, with Red X deliberately placing himself in situations where he might be caught in order to help Robin (and, by extension, the rest of the Titans). It's made most obvious in the episode "Revved Up" when the two are racing on their motorcycles (and against other villains) in order to be the first to steal an already once-stolen case that is incredibly important to Robin. After a stray bomb throws Red X from his bike, Robin saves Red X's life by grabbing him out of mid-air and pulling him onto Robin's own motorcycle.
Red X: The briefcase really means that much to you?
Robin: (Grimly) You have no idea.
Red X: Then go get it. (Leaps off the back of the R-Cycle)
Twilight Sparkle: Joe is not sleek, stealthy Con Mane! He's big, gruff, and messy!
In his memoirs, Bad Ass early 1900s detective Frederick Porter Wensley refers to the Spider, a brilliant Gentleman Thief who turned to a life of crime for a sense of adventure.
The "Dean of American Bank Robbers," Harvey Bailey.
John Dillinger counted.
There was a period when the fashion for stage magicians included exploiting this image, and when performing for wealthier groups part of the act would usually include mingling with and pickpocketing from the audience (and ostentatiously returning the loot).