• Smuggling
• Rum-running, the sale or transport of liquor without regard to legal regulations and taxes
• Bootleg role-playing games, illegally copied rulebooks for tabletop role-playing games
• Bootleg mining, hidden or illegal coal mining
• Bootleg (radio), the use of illegal equipment, frequencies, or operating procedures in two-way radio
• Bootlegging (business), the secret organization of an innovation process
• Bootleg (TV serial), a 2002 BBC miniseries for children that's an adaptation of the novel of the same name by Alex Shearer. It may also refer to the manga series "Chocolate Underground" which itself was based on the book series.
• Bootleg (comics), a character from the comic book New Men
• Bootleg play, a tactic in American football
• Bootleg turn, a driving maneuver
• Bootleg (magazine), a student newspaper at the University of Ballarat in Australia
• Bootleg Skateboards A skateboarding company
• Bootleg (Emulation)
• Bootlegging, a common colloquial slang term amongst owners of railroad speeders to describe the illegal operation of a Speeder on a railway.
• Bell-bottoms or bootleg pants, trousers which flare out at the bottom of the legs and may cover the wearer's shoes Bootlegger- a person who makes liquer or hard drinks

  Music

• Bootleg recording, an otherwise unavailable audio or video recording distributed without the artist's consent
• Copyright infringement, the making of unauthorized duplicates of material already commercially available
• Counterfeit merchandise
• Mashup (music), music which contains unlicensed samples of other music
• Live Bootleg (album), a number of albums
• Bootleg (Larry Norman album)
• Bootleg (Bad News album)
• Boot-Leg, a song by Booker T & the MG's

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