Top 10 Craziest Mike Tyson Moments

Back in 2018, when controversial YouTuber Jake Paul started boxing, we all shared a bit of a laugh. But his career has become far more successful than anyone could have anticipated, and now he’s fighting freaking Mike Tyson in front of 100,000 people. Yes, Tyson is obviously well past his prime at 58, but this is about spectacle and entertainment more than anything else, and it’s fantastic to see the legendary boxer climbing back into the ring. The fight is to consist of eight two minute rounds and is set to be broadcast live on Netflix in November 2024. Even at this stage of his life, Tyson is still finding new ways to entertain and remain relevant to younger generations.

If there’s one thing that stains an otherwise stellar reputation, it’s Tyson’s criminal record. In July of 1991, Tyson was accused of sexually assaulting Desiree Washington in an Indianapolis hotel room. Washington pressed charges, and Tyson was famously convicted in 1992, being sentenced to six years in prison. He served less than three. Tyson’s imprisonment significantly damaged his public image, as he went from one of the most feared and admired athletes in the world - maybe even in history - to a highly polarizing figure. His prison sentence also took away three of his prime fighting years, allowing other athletes to steal the spotlight. He was never quite the same after this.

On May 20, 1986, Tyson defeated Mitch Green via unanimous decision. Fast forward two years to August 23, 1988, when Green confronted Tyson outside of Dapper Dan’s Boutique, a popular clothing store in Harlem. What happens next is hard to say, but words are exchanged and the verbal fury soon turns physical. According to Green, he was suckerpunched by Tyson. According to Tyson, he was defending himself from Green. Regardless, a brawl erupted in the street and Tyson left his opponent mangled with a swollen eye and a broken nose. In fact, the beating was so severe that Tyson actually thought he had killed Green, and the fight solidified his near-mythical reputation as an unbeatable fighter.

History was made inside the Las Vegas Hilton on the evening of November 22, 1986. It was Judgment Day - not the Judgment Day, that’s just what it was called - and Mike Tyson was facing WBC heavyweight champion Trevor Berbick. Tyson dominated from the outset, establishing himself as the aggressor and hitting Berbick with a flurry of punches that sent him reeling. It was obvious from the very first round that Berbick was in trouble, and he went down twice in the second. He desperately tried to stand, but could only stumble, causing referee Mills Lane to call a TKO. And that’s how Mike Tyson became the youngest heavyweight champion in boxing history - a record that still stands at 20 years, 4 months.

The win against Berbick was just one part of a larger story - that of unifying all three major heavyweight belts. By the 1980s there were three different champions in three different organizations, confusing fans and diluting the legitimacy of the belt-holders. Enter legendary promoter Don King, who crafted the heavyweight unification series, which was designed to unify all three belts and officially name an undisputed champion. We’ll let you guess who won. After beating Berbick for the WBC title, Tyson then defeated James Smith and took his WBA belt. And then, on August 1, 1987, Tyson defeated Tony Tucker via unanimous decision, winning the IBF belt and becoming the first boxer to hold all three at once.

“Once and For All” was the most anticipated fight of its day, a dramatic showdown between two undefeated titans - Mike Tyson and lineal champion Michael Spinks. Thousands of people paid top dollar to crowd Convention Hall in Atlantic City - and the fight was over in ninety seconds. Ah, the unpredictable beauty of boxing. Yep, Tyson dropped Spinks twice in the span of fifteen seconds - and that’s including the ref count! The first was a wicked body shot that took Spinks to his knees. He quickly recovered, only for Tyson to immediately down him again with a powerful right hand. Spinks was sent to la la land, and Tyson was cemented as the most feared and dominant fighter of his era.

Mike Tyson simply dominates the cultural conversation - if it’s not boxing, it’s owning one of the most distinctive and recognizable tattoos in history. Tyson originally wanted to get hearts on his face, but tattoo artist S. Victor Whitmill shut that down, instead going for a tribal design inspired by the Māori practice of Tā moko. While Tyson faced some criticism for cultural appropriation, the tattoo was instantly iconic and became a defining aspect of his public character. Its warrior distinction was further solidified following his fight with Clifford Etienne, whom Tyson knocked out in just fifty seconds.

By 2002, Mike Tyson was well past his prime, but he was still winning fights and making headlines. One of the most infamous moments of his career came on January 22, during a press conference to announce an upcoming fight with Lennox Lewis. Tyson approached Lewis on the stage of the Hudson Theatre and threw a punch at one of Lewis’s bodyguards, resulting in an enormous brawl. WBC president José Sulaimán was knocked out after hitting his head on a table and later sued Tyson for $56 million. Tyson also admitted to biting Lewis’s leg during the scuffle and later paid him over $300,000 in damages. And all this happened before his profanity-laced tirade aimed towards the crowd. Yeah, it was a whole thing.

If you want a real life “Rocky”, watch the fight between Tyson and Buster Douglas. The two were scheduled to fight on February 11, 1990, with Douglas being the 42-1 underdog against the undefeated Tyson. This was widely expected to be another routine win for the champ, with reporters openly joking about Douglas’s chances and Tyson partying the night before the fight. But the bout was unexpectedly competitive, with Tyson struggling to deal with Douglas’s range and composure. And then came the tenth round, when Douglas knocked Tyson down for the first time in his career - and he stayed down. It was Tyson’s first professional loss, and it shattered the myth of his invulnerability. Tyson himself later quipped, “My career has been over since 1990.”

There are certain moments in sporting history that transcend the game itself - moments that become pop culture icons, widely known even to those who don’t follow the sport in question. This is certainly the case with the infamous ear bite. It occurred on June 28, 1997, when Tyson was fighting Evander Holyfield. Tyson was getting battered, and, after growing increasingly frustrated, decided to take a chunk out of Holyfield’s ear. But wait, there’s more - after getting a stern warning, he did it again! Tyson was swiftly disqualified, making this the first time in 56 years that a title fight ended in a disqualification. That’s certainly one way to leave a legacy!

What do you make of the legendary boxer? Let us know in the comments below!