Taking acid (1977)
Growing up in Brooklyn’s tough Brownsville neighborhood, Tyson’s childhood was marked by exposure to crime and substance abuse. He revealed on the Joe Rogan Experience podcast that by the age of 11, he had already experimented with acid after starting with smoking and drinking at nine.
Winning a match while battling an STI (1986)
At just 20 years old, Tyson became the youngest WBC heavyweight champion in history by defeating Trevor Berbick via technical knockout in the second round. In his autobiography, Tyson disclosed that he fought while being treated for a sexually transmitted infection (STI).
Offering to fight a gorilla (1989)
During a private visit to the New York Zoo with his then-wife Robin Givens, Tyson reportedly offered a zookeeper $10,000 to let him fight a silverback gorilla, but his offer was declined.
Getting a prison guard pregnant (1992-1995)
While serving a nearly three-year prison sentence for rape, Tyson admitted to having a relationship with a female prison guard. He claimed the two had frequent sex, resulting in her pregnancy.
Biting Evander Holyfield’s ear (1997)
In one of boxing’s most infamous moments, Tyson bit Evander Holyfield’s right ear during their heavyweight title fight, spitting out a piece of it. Despite the injury, the match continued, only for Tyson to lightly graze Holyfield’s left ear later in the same round. Tyson was disqualified after that.
Talks of a third fight with Holyfield resurfaced in 2021 but fell apart over financial disagreements, as Tyson declined the $25 million offer.
Entering the ring while getting high (2000)
In his 2013 autobiography, Tyson admitted to using cocaine and marijuana before his first-round knockout victory over Lou Savarese at Hampden Park.
Passing doping tests with a dildo (2000)
To avoid failing drug tests, Tyson used a "whizzinator," a prosthetic device filled with clean urine, to deceive testers during his career.
Brawling with Lennox Lewis at a press conference (2002)
Before their fight, Tyson punched one of Lennox Lewis’ bodyguards at a press conference in New York, igniting a chaotic brawl between the two. When they finally met in the ring at the Pyramid Arena in Memphis, Tennessee, Lewis knocked out Tyson in the eighth round.
Tyson competed in 58 professional fights from 1985 to 2005, winning 50 (44 by knockout) and losing six. Lewis enjoyed an equally impressive career, winning 41 of his 44 fights, with 32 victories by knockout.
