The Crazy Gang is a nickname coined by the English media in reference to the Wimbledon F.C. teams of the 1980s and '90s. The name, originally that of a well known group of British comedy entertainers popular in the late 1930s, became commonly associated with Wimbledon as a result of the often cheeky and boisterously macho behaviour of their players, who were in the habit of playing frequent and outrageous practical jokes on each other and on the club's managers Dave Bassett, Bobby Gould and Joe Kinnear, as well as many of their players' highly aggressive, physical style of play and reputation for a lack of discipline on the pitch.
Despite enjoying decent success as a fixture in the First Division and later Premier League at the time, their general approach to the game was often derided by others in the sport as unprofessional and simplistic in comparison to the style of football played by most of their top-flight contemporaries at the time; then England striker Gary Lineker once commented dismissively, "the best way to watch Wimbledon is on Ceefax", criticising the team's supposedly unsophisticated approach to football. As the now top-flight team received more attention for their antics from the media, they also became subject to constant criticism from many pundits and fellow players, who accused the team of a simplistic, overly aggressive, and intimidating approach to football in comparison to the other teams in the league. This newfound scrutiny created a close bond and tenacious camaraderie among the players, who adopted an "us vs them" mentality on the field as more and more opposing teams feared the side and their reputation.
As the team saw a sustained degree of success in the First Division, their most famous moment came in 1988, when they upset league champions Liverpool to win the FA Cup. The "Crazy Gang" nickname was coined at the final whistle, when BBC commentator John Motson declared that "The Crazy Gang have beaten the Culture Club". The name then caught on nationally, frequently appearing in newspaper reports, and was often used in TV and radio coverage of the club. The team finished seventh in the league that season, having finished sixth a year earlier on their debut in the top flight.