• Boss (crime), the head of a criminal organization
• Air boss, more formally, air officer, the person in charge of aircraft operations on an aircraft carrier
• Fire boss, a person in charge of mine safety
• Pit boss, the person who looks after the employees who work in a casino pit
• Political boss, a person who controls a political region or constituency

• Boss, Missouri, United States, an unincorporated community
• Boss, Texas, United States, an unincorporated community
• Bosstown, Wisconsin, United States, an unincorporated community
• Boss (crater), a lunar crater

As a real name

• Boss Mustapha, politician, Secretary of Nigerian government
• Hugo Boss (fashion designer) (1885-1948), German businessman and founder of clothing company Hugo Boss

As a nickname or stage name

Athletes

• Lance Armstrong ("Le Boss", born 1971), former professional cyclist
• Tomás Boy ("El Jefe", born 1952), former Mexican professional football player and current coach
• Bobby Lashley (born 1976), professional wrestler
• Helmut Rahn ("Der Boss", 1929–2003), German football player
• Andrew Reynolds (skateboarder) (born 1978)
• George Steinbrenner (1930–2010), owner of the New York Yankees baseball team
• Jos Verstappen (born 1972), Dutch Formula One driver

Musicians

• Boss (rapper) (née Lichelle Laws, 1969), American rapper
• Gene Ammons ("The Boss", 1925–1974), American jazz musician and songwriter
• Ross the Boss Friedman (born 1954), guitarist of The Dictators and Manowar
• Diana Ross ("The Boss", born 1944), American singer and actress
• Rick Ross ("The Boss", born 1976), American rapper
• Bruce Springsteen ("The Boss", born 1949), American singer and songwriter

Politicians

• Richard J. Daley (1902–1976), former mayor of Chicago, Illinois, United States
• Boss Shepherd (Alexander Robey Shepherd, 1835–1902), Washington, D.C., politician
• Boss Tweed (William M. Tweed, 1823–1878), notoriously corrupt New York City politician

Other people

• Ernest Shackleton (1874–1922), Anglo-Irish explorer

Fictional characters

• Boss (Mazinger), from the anime Mazinger Z
• Big Boss (C.O.P.S.), a crime boss from the animated series C.O.P.S.
• Big Boss (Metal Gear), a character in the Metal Gear video game series
• Boss Hogg, the main villain of the television show The Dukes of Hazzard
• Pointy-haired Boss, the office nemesis of cartoon character Dilbert
• The Boss (Metal Gear), a character in the video game Metal Gear Solid 3: Snake Eater
• "The Boss," title bestowed upon the narrator of A Connecticut Yankee in King Arthur's Court
• "The Boss", Nicolas Lucifer III, from the animated series The Baskervilles
• "The Boss" (simply known as "playa" in the first game), the main character of the Saints Row series

Film

• The Boss (1915 film), a silent film based on a play by Edward Sheldon (see below)
• The Boss (1956 film), an American film by Byron Haskin
• The Boss (1973 film) or Il Boss, an Italian crime film
• The Boss (1975 film) or Boss Nigger, a blaxploitation film
• The Boss, a 2005 short film starring Jennifer Sciole
• Boss (2006 film), an Indian Telugu-language film
• Boss (2011 film), an Indian Kannada-language film
• Boss: Born to Rule, an Indian Bengali-language film starring Jeet
• Boss (2013 Hindi film), an Indian Hindi-language film starring Akshay Kumar
• The Boss (2016 film), an American film starring Melissa McCarthy

Music

Bands

• Boss (Australian band), a 1980s hard rock band
• The Boss (band), a South Korean boy band

Albums

• Boss (album), by Magik Markers, 2007
• The Boss (Diana Ross album), 1979
• The Boss (Jimmy Smith album), 1968
• The Boss (Timati album), 2009

Songs

• "Boss" (Fifth Harmony song), 2014
• "Boss" (Lil Pump song), 2017
• "The Boss" (Diana Ross song), 1979
• "The Boss" (Rick Ross song), 2008
• "The Boss", a song by James Brown from the soundtrack of the 1973 film Black Caesar
• "The Boss", a song from the 2007 Sivaji film soundtrack album

Television

• Boss (TV series), a 2011 US series starring Kelsey Grammer
• The Boss (TV series) or The Peter Principle, a British television sitcom
• "Boss", an episode of Life's Work
• Bimorphic Organisational Systems Supervisor, fictional supercomputer in the Doctor Who television serial The Green Death

Other

• Boss (video gaming), a particularly powerful enemy or opponent in a video game
• Boss Radio, a 1960s pop radio format
• Boss: Richard J. Daley of Chicago, a 1971 book by Mike Royko
• The Boss, a 1911 Broadway play by Edward Sheldon

• Boss (geology), a body of igneous rock
• Boss (engineering), an engineering term for a protrusion type feature
• BOSS (molecular mechanics) (Biochemical and Organic Simulation System), a molecular modeling program
• Balanced Optical SteadyShot, an image stabilization technology used in Sony video cameras
• Baryon Oscillation Spectroscopic Survey
• BOSS Great Wall, the largest known galaxy wall
• Bharat Operating System Solutions, GNU/Linux distribution