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Italian WWII propaganda poster presenting an Allied airman as a gangster, playing on the popular gangster icons of Al Capone and the Thompson M1928 gun.

Gangster is the frequently misused term for a career criminal who is, or at some point almost invariably becomes, a member of a persistent violent crime organization, such as a gang. As an adjective it can be used as an unflattering depiction of the violent and devious methods commonly used by mobsters, and the derived form gangsterism it implies such methods as practice or habit.

In the WWII era, the word "gangster" became a popular term to describe an individual who was a part of a "mafia" or "organized crime group". In current times, gangsters are most commonly viewed as malicious individuals. The media has had a substantial influence on the modern view of the gangster.

Gangsters are typically organised criminals who are actively engaged in crime as a group activity or enterprise for pleasure and profit. The visibility of activities of gangsters can range from the low-level such as drug-trafficking or protectionism, which are prone to be 'under the radar', to the in-your-face spectacular, such as the UK's multi-million Brinks Mat robbery. Gangsters often run their operations as businesses insofar as they offer a "product" or "service", albeit an illegal one, or, as is sometimes the case, a legitimate business operating as a front for criminal activity.

The ranges and spheres of activities of gangsters are diverse, and frequently are to be found filling the gaps between legislature and physical reality. During the Prohibition era in the United States, gangsters effectively and lucratively exploited the demand for alcohol by filling the gap in supply. In the 1950s, they did the same with gambling. They also actively engage in other demand-driven markets such as trade in narcotics, pimping, people-trafficking, the supply of false documents, and so on and so forth.

Some gangsters engage in extortion, intimidation, and/or bribery to wield influence over labor unions. They are also known for attempting to manipulate the decisions of civil institutions, such as court cases and political elections.

Britain has a long and lurid tradition of gangsters, and an ambivalent relationship with them. In Britain a career in crime can also be a useful entrypoint to the media; examples of gangsters who have gone mainstream include "Dodgy" Dave Courtney, "Mad" Frankie Fraser and John McVicar. The epitome and true viciousness of much British gangsterism can, however, be better characterised by the turf wars between the Kray twins (and their associates) and the Richardson gang. The infamous James "Full Cone" Still and ETS Boys are notorious throughout the UK for their past dealings with rival gang E2S, which involved much bloodshed.

Gangsters have long been a staple of both film and other media. Notable media depictions of gangsters include:

• James Cagney as Tom Powers in The Public Enemy
• Larenz Tate as O-Dog in Menace II Society
• Grand Theft Auto, a computer and video game series
• Orson Welles as Harry Lime in The Third Man, based on a novella by Graham Greene
• Marlon Brando as Vito Corleone and Al Pacino as Michael Corleone, and several other characters in The Godfather
• Robert Shaw as Doyle Lonnegan in The Sting
• Ray Liotta as Henry Hill in Goodfellas
• The Krays
• Al Pacino as Tony Montana in Scarface, and Carlito Brigante in Carlito's Way
• Robert DeNiro as Sam "Ace" Rothstein in Casino, also as Al Capone in the The Untouchables
• Samuel L. Jackson, John Travolta, and Ving Rhames in Pulp Fiction
• James Gandolfini as Tony Soprano in The Sopranos
• Gangster the book by Lorenzo Carcaterra
• "Reservoir Dogs," a movie by Quentin Tarantino
• Redemption: The Stan Tookie Williams Story
• Sylvester Stallone as Angelo "Snaps" Provolone in the 1991 comedy Oscar
• Snatch. (film) is a British gangster film (2000)