- See also: The Caper, The Con.
- Examples: Hustle, It Takes a Thief (1968), Lupin III, Ocean's Eleven, Leverage
- See also: The Aggressive Drug Dealer (antithesis)
- Examples: Weeds, Lock, Stock..., Breaking Bad (roughly first half), Ideal.
- Examples: The Sopranos, The Wire, The Godfather (Book and Movie), Breaking Bad (roughly second half)
- See also: Prison, Prison Rape, Luxury Prison Suite
- Examples: Oz, Prison Break, Porridge, Orange Is the New Black
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Anime, Light Novels, and Manga
- Lupin III is an action/comedy Franchise about a Gentleman Thief and his accomplices.
- Black Lagoon encompasses just about all four types of "people outside the law" and even introduces characters that seem to fit in a criminal archetype all their own.
- Cat's Eye is about a team of sisters trying to steal back their inheritance Gentleman Thief style.
- Hard Time was a short-lived but critically acclaimed DC Comics series that combined convicts in prison with more fantastic elements. (It did not take place in The DCU.)
- Secret Six straddled the line, focusing on a team of villains who were initially bootstrapped together by a mysterious backer, but banded together while taking "gray jobs" to make money.
- To Catch a Thief had Cary Grant as a suave jewel thief who supposedly had retired, until thefts in his style started happening again...
- Catch That Kid. A movie about a girl and her friends who team up to rob the bank her mother works for to pay for her father's surgery.
- The Hot Rock: Robert Redford as Gentleman Thief Dortmunder. See Literature below.
- The Sting: Robert Redford and Paul Newman team up to scam a racketeer. The inspiration for and referenced by many others on this list.
- The Sting II
- Sneakers: Robert Redford as the leader of a team of shady (but mostly licit) "security experts".
- Butch Cassidy and the Sundance Kid: Robert Re... look, let's just say that Robert Redford really likes the Gentleman Thief type and capers.
- Quentin Tarantino likes this genre as well. Reservoir Dogs follows a cadre of bank robbers (and one undercover cop) on a heist that goes pretty far awry.
- Also from Tarantino is Pulp Fiction, whose main characters are two contract killers, their imposing boss, a boxer who's killed a man in the ring by way of ripping the boss off, and two sweetheart stickup artists whose victims include the contract killers, although "victim" isn't really the right word.
- The Hot Rock and all of Donald E. Westlake's "Dortmunder" books involve cons, capers, criminals, and gentlemen thieves.
- Also from Westlake (under his Richard Stark psuedonym), the Parker novels. In contrast to the Dortmunder books, the Parker books are dark, violent, and star an utterly amoral Villain Protagonist.
Live Action TV
- Boardwalk Empire explores the organized crime ventures and opportunities opened in the wake of the Volstead Act in New Jersey, New York and Chicago.
- Breaking Bad about a mild-mannered high school chemistry teacher turned meth cook turned drug kingpin. Features an excellent progression for a Villain Protagonist, it transitions from petty/hanger-on to hardcore organized crime over about a season (at the beginning of Season 3, he hasn't even told his wife about his side business; at the end, he has already ordered a hit and his wife is laundering his money).
- Dexter follows Dexter Morgan, a forensic specialist by day and serial killer by night. Interestingly, also a Police Procedural.
- Gangland Undercover, is an American factual drama miniseries about Charles Falco, a former ATF confidential informant who infiltrated an outlaw motorcycle gang.
- Hap and Leonard is a drama series based on the characters Hap and Leonard, created by novelist Joe R. Lansdale and adapted by his series of novels of the same name.
- Hustle is a British TV series about a group of con artists, heavily inspired by the remake of the movie Ocean's Eleven.
- Ideal is a sitcom about a small-time drug dealer.
- Intelligence (2006) is partly about an organized crime group engaged in the marijuana trade.
- It Takes a Thief (1968) with Robert Wagner was probably the first television program to do this.
- Leverage: A formulaic but truly fun show where a band of True Companions conmen/thieves/hitters/hackers/etc. take down the rich and greedy.
- Lock, Stock..., a spin-off from the movie Lock, Stock & Two Smoking Barrels, featured a gang of Outsiders who invariably ended up on the wrong side of much nastier London gangsters.
- Oz is an infamously violent show set in a US prison with a multitude of rapes, castrations, murders and more rapes.
- Porridge is a Brit Com set in a small prison.
- The Saint was a Gentleman Thief with Robin Hood tendencies, although the TV version downplayed this, portraying him more as an Amateur Sleuth whom a police detective had an inexplicable grudge against.
- Murphy's Law is about undercover cop Tommy Murphy and the various criminal organizations (and in some cases, prisons) he enters.
- Orange Is the New Black is Based on a True Story about a woman who was sent to prison for helping her girlfriend transport drug money. The series also focuses on other prisoners and uses flashbacks to detail their crimes.
- Peaky Blinders based on a Real Life street gang in early 20th century Birmingham (the English one), and their attempts to gain prominence in the underworld against more powerful and influential gangsters. Also features some very bent coppers as well as appearances from the IRA, communists, anarchists and a pre-Prime Minister Winston Churchill.
- Power: Ghost, a powerful drug dealer, attempts to go legit by opening a night club. However, many of his associates are against this, including his wife. And many of his enemies sees this an act of weakness and an opportunity to take over his empire.
- Red Widow: The daughter of a Mafiya boss who has to continue the criminal work of her husband after he is killed.
- Sons of Anarchy is about an outlaw motorcycle club operating a variety of criminal activities ranging from petty to extreme. Shades of grey abound, but even some of the most murderous characters are oddly lovable.
- The Sopranos is probably the best known example: a high-profile, critically acclaimed show following the exploits of Tony Soprano, mafia boss, and the various members of his two families.
- The Straits is about the deadly smuggling trade between northern Australia and Papua New Guinea. It focuses on infighting in the Montebello crime family, but also how a drug trade between a developed nation (Australia) and a developing nation (PNG) impacts the people on all sides who get caught up in it.
- Weeds is a comedy/drama about a bereaved housewife who starts selling marijuana to pay the bills.
- The Wire tends to be evenly split between the lives of the criminals and the lives of the cops that are stalking them. Later seasons broadened this to politicians, journalists, and children who are getting into a life of crime.
- The Americans examines what it takes to be an illegal spy (sleeper KBG agent) in Reagan's United States. It involves murder and deception of regular people on a regular basis.
- Narcos chronicles the drug empire built by Pablo Escobar and the efforts to capture him.