Tyson's career revival, following his shocking first career defeat to underdog James 'Buster' Douglas and his subsequent imprisonment for rape, was wrecked by Evander Holyfield in their first meeting in November 1996.
The extraordinary pressures he faced both in and out of the ring would manifest in one of the most shocking events in sporting history, and one which served to re-establish Tyson's notoriety for all the wrong reasons.
Tyson's second coming had been a relatively facile affair, with inconsequential wins over Peter McNeely and Buster Mathis Jr. leading up to a third-round stoppage of Frank Bruno to reclaim the WBC title.
Such was the aura surrounding Tyson that it was enough to make him the overwhelming favourite for his first fight with Holyfield, who had previously retired with a heart condition and for whom the build-up to the bout was punctuated by serious concerns for his health.
Holyfield responded by delivering a masterful performance to quell Tyson's rage and force referee Mitch Halpern's intervention with Tyson out on his feet in the 11th round. It made a rematch both inevitable and lucrative.
From the outset of their second bout at the MGM Grand in Las Vegas, it was apparent that Holyfield was well-placed to repeat the feat and potentially deal Tyson's championship career a terminal blow.
Tyson appeared to grow increasingly frustrated by Holyfield's use of his head, about which he had complained in the wake of their first meeting, and which quickly opened a cut over his right eye.
Exasperated, Tyson came out for the third round without his gumshield and was ordered to return to his corner by referee Mills Lane. After a furious exchange, Holyfield reeled back and complained that Tyson had bitten a chunk out of his right ear.
The fight was briefly delayed while Lane considered his next move. Eventually, he allowed it to continue but waved it off when Tyson proceeded to bite Holyfield's left ear. Tyson raged at the stoppage, and security personnel had to protect Holyfield in his corner.
Later, Tyson did not try to hide his assault. "Holyfield kept butting me," he told the media. "What am I supposed to do? I've got children to raise. He's not a warrior. He's got a little nick on his ear. He didn't want to fight me."
In the post-fight chaos, Tyson was hit by a water bottle on his way back to the dressing room, and he and his entourage attempted to scale barriers to confront the culprit. Shots were fired in the MGM Grand lobby on what descended into one of boxing's blackest nights.
Tyson's boxing licence was revoked by the Nevada State Athletic Commission and he was fined £3million. Allowed to return just over a year later, he reeled off a succession of low-key wins until he was swatted by Lennox Lewis in Memphis in June 2002.
Holyfield, who had subsequently lost his titles to Lewis, fought on and won a series of low-key versions of the title. He had his last fight at the age of 48, when he was stopped by Brian Nielsen in Denmark.
Tyson and Holyfield made up and eventually became close friends. They appeared together on the Oprah Winfrey Show in 2009, when Holyfield said he forgive Tyson, and Tyson responded by calling Holyfield a "gentleman".
In retirement, the 'Baddest Man on the Planet' had finally started to repair his reputation. But a quarter of a century on, his ferocious career is still defined by the so-called 'Bite Fight' that dragged heavyweight boxing into the gutter.