When Boxers Meet Entertainers

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  • Muhammad Ali and Sam Cooke
  • Muhammad Ali and James Brown
  • Mike Tyson and Canibus
  • Mike Tyson and Tupac
  • 50 Cent and Floyd Mayweather
  • Martin Lawrence and Tommy "Hitman" Hearns
  • Floyd Mayweather and Justin Bieber
  • Mike Tyson and The Hangover Cast
  • Joe Louis and Frank Sinatra
  • Muhammad Ali and the Beatles

Mike Tyson and Canibus

Mike Tyson joined rapper Canibus for his 1998 LL Cool J dis song, "Second Round K.O.," adding his unique vocals and appearing in the video. (Photos from left: Hayley Madden/ Redferns, Chris Hyde/Getty Images)