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A bootleg is the upper part (or shaft) of a boot.

Bootleg, bootlegging or bootlegger(s) may also refer to:

• Rum-running, the illegal business of transporting and trading in alcoholic beverages
• Moonshine, illicitly made and/or distributed alcohol
• Bootleg recording, an audio or video recording released unofficially
• Counterfeit copies of existing toys and games (including video games and video game consoles) manufactured and sold without license from the intellectual property holder.

• Bootleg trousers, a kind of bell-bottomed trousers
• Bootleg, a brand name used by C. & J. Clark for children's shoes and trainers

• Bootleg (TV series), a 2002 miniseries for children
• Bootleggers (1961 film), a Soviet short film about alcohol bootlegging
• Bootleggers (1969 film), an Italian-Spanish crime-action film
• Bootleggers (1974 film), an American crime film
• Bootleg (1985 film), a 1985 Australian film
• Bootlegger (2021 film), a 2021 Canadian film

• "Boot-Leg", a song by Booker T & the MG's
• Bootleg (Bad News album), released 1988
• Bootleg (Downchild Blues Band album), released 1971
• Bootleg (Larry Norman album), released 1972
• Bootleg (Tempest album), released 1991
• Bootleg (Kenshi Yonezu album), released 2017
• Bootlegs (Kristy Thirsk album), released 2000
• Bootleg, a 2004 album by Avenue D
• Bootleg, a 2007 album by Eric's Trip
• "Bootleg", a song by Creedence Clearwater Revival from Bayou Country
• "Bootleg", another term for a mashup

• Bootleg (character), fictional superheroine in the comic book New Men
• Bootleg radio, also known as pirate radio
• The Bootleggers, a 1961 non-fiction book by Kenneth Allsop

• Bootlegging (business), practicing unauthorized research activities within an organization
• Bootleg Fire, a 2021 Oregon wildfire
• Bootleg mining, a mining practice involving small, illegal mines
• Bootleg play, a tactic in American football
• Bootleg turn, a driving maneuver

• "Bootleggers and Baptists", an economic theory that ostensibly opposing groups will often support similar legal restrictions on trade
• All pages with titles containing bootleg
• Live Bootleg (disambiguation)