When considering the most significant moments of Mike Tyson’s career, it’s not all about triumphs. Some instances, like an ear-biting incident, aren’t exactly things to celebrate. Nevertheless, Tyson has a multitude of moments to reflect on, as he ranks among the most notable athletes ever. Hence, we will review his best and worst moments.

Tyson’s impact goes beyond boxing; he even starred in the film “The Hangover.” Over the years, he has managed to soften his tough image through commercials and guest spots on late-night shows. Few public figures have maintained such a level of fame and relevance as Tyson for decades. His upcoming match against Jake Paul is generating a lot of buzz for this reason.

Listing Tyson’s most significant moments is no simple task. Here are 10 noteworthy instances:

10. Holyfield I, 1996

In this match, Evander Holyfield defeated Tyson by TKO in the eleventh round. Why is a loss included here? It marked a pivotal event in boxing, showcasing the sport’s significance. This fight played a critical role in elevating Tyson’s status to a cultural icon.

9. Knockout of Trevor Berbick, 1986

This fight exemplified Tyson’s incredible punching power. He unleashed a combination that left Berbick reeling. It created a dual effect of intimidation among opposing boxers and fascination from the audience.

8. “The Hangover,” 2009

The movie isn’t as hilarious as some might think, in my opinion. However, Tyson’s role was memorable and arguably the highlight of the film. Even if the movie is overrated, his performance stood out.

7. Fights against Donovan “Razor” Ruddock, 1991

Tyson faced Ruddock twice that year, demonstrating his sheer force. In their second match, Tyson notably broke Ruddock’s jaw, furthering his fearsome reputation.

6. Candid Interview, 1999

In this interview with Russ Salzberg, the contrast between Tyson then and now became apparent. The current Tyson shows a more refined image, but back then, he was brazen and unfiltered, revealing a raw side of his personality.

5. Mike Tyson Makes a Comeback

After retiring in 2005, Tyson returned to boxing, likely motivated by financial incentives. His upcoming fight against Paul seems poised to generate less excitement, yet Tyson continues to capture public interest.

4. Tony Tubbs, 1988

This fight may not be among Tyson’s most renowned, as Tubbs wasn’t a big name. However, the bout took place in Tokyo, aiming to build international appeal, and Tyson’s fame was already immense.

3. The Infamous Ear-Biting Incident, 1997

During the second bout with Holyfield, Tyson bit his opponent’s ear in the third round, leading to his disqualification. This shocking moment revealed Tyson’s darker side and left the boxing community in disbelief.

2. Buster Douglas Shocks the World, 1990

This moment was monumental; Tyson was undefeated, and Douglas was a considerable underdog. No one envisioned Tyson losing. This is regarded as one of boxing’s greatest upsets and ranks among the top five in American sports history. Douglas downed Tyson in the tenth round, and Tyson could not rise before the count. Douglas attributed his victory to his mother; it was a poignant moment.

1. The Birth of the Tyson Legend, 1988

Michael Spinks wasn’t only a remarkable boxer, but he was also considered one of the greats at that time—possessing similar power to Tyson and speed to match. Many experts favored Spinks to win, but Tyson delivered a knockout in just 91 seconds.

This knockout solidified the myth of Tyson as the most feared fighter ever, explaining why he still draws an audience today.