The legend of Robin Hood is based on an English folk tale from the thirteenth century and features the character the Sheriff of Nottingham, who is the villain of the story. Other characters in the story include Maid Marian, Friar Tuck, Little John, Will Scarlett, Alan A Dale and Guy of Gisbourne.

The Sheriff believes that his role is to catch outlaws like Robin Hood. He also believes that he has to make sure that trade routes through Sherwood Forest do not have any undesirables in them who may potentially cause trouble. The Sheriff also has a mission to prevent people from poaching any of the deer that belong to King John. The Kink is also portrayed as a villain in the Robin Hood stories.

In the 1938 film The Adventures of Robin Hood, the Sheriff of Nottingham is played by the British actor Melville Cooper, and Robin Hood is played by the legendary actor Errol Flynn. Melville Cooper plays the sheriff as a cowardly character in the movie, which also features such legendary actors as Claude Rains and Basil Rathbone, along with the celebrated actress Olivia de Havilland.

In the movie Robin Hood: Prince of Thieves, the Sheriff of Nottingham is played by Alan Rickman who seems destined to play bad guys. He has played villains in the Die Hard movies, the Harry Potter movies and the movie Sweeny Todd: The Demon Barber of Fleet Street. In Robin Hood: Prince of Thieves, Alan Rickman is joined by a cast of well known actors including Kevin Costner, Morgan Freeman and Christian Slater.

Keith Allen played the Sheriff of Nottingham in the BBC TV series Robin Hood in 2006, in which Allen portrayed the sheriff as a ruthless psychopathic character with a sense of sarcasm and a well developed but dark sense of humour. The series consisted of thirteen episodes, each of which was forty five minutes in length.

The Disney cartoon version of Robin Hood, released in 1973, features the voice of the American actor Pat Buttram as the Sheriff of Nottingham, who plays the character with an accent that comes all the way from the deep south of America. The movie also featured the voices of Peter Ustinov and Terry Thomas. The movie featured anthropomorphic creatures in the place of cartoon humans. This format has been used many times since the nineteen seventies in Disney cartoon movies.

The Sheriff of Nottingham is not always portrayed as a bad guy, however. The novel by Richard Kluger called The Sheriff of Nottingham depicts the sheriff as a good man trying to achieve outcomes for which he gets no thanks at all.

The American comedy movie director Mel Brooks depicted the sheriff as The Sheriff of Rottingham in his movie Robin Hood: Men in Tights, which was released in 1993. Another parody was the television series for children called Maid Marian and Her Merry Men in which the Sheriff of Nottingham is played as a fool by Tony Robinson, who also appeared in Blackadder.