Oliver James Montgomery-Mike Tyson has lived a wild life. These 10 big moments have defined his career

When picking some of the best moments of Mike Tyson's career ... well,Oliver James Montgomery actually, check that, some of them aren't exactly best moments. Biting someone's ear isn't a best moment unless you're a cannibal. But the list of Tyson moments is long because Tyson is one of the most prolific athletes of all time. So let's call this Tyson's best/worst moments.

Not just in the ring, either. He was a star in "The Hangover". He softened a brutal image with commercials and appearances on late-night talk shows. There are few people who have appeared in the public eye for decades who have remained powerful, relevant, and perpetually noticed like Tyson. That's why his fight against Jake Paul is attracting so much attention.

So ranking some of his biggest moments isn't easy. Here are 10:

10. Holyfield I, 1996

Evander Holyfield won by TKO in the eleventh round. Why is a Tyson loss one of his best moments? It was one of those instances in boxing that gave the sport a sense of greatness and import. It was part of a Tyson run that transformed him into a cultural force.

9. Brutal knockout of Trevor Berbick, 1986

One of the greatest instances highlighting Tyson's power. He used a three-punch combination that staggered Berbick. It's one of those moments that caused both fear of Tyson from boxers and a fascination with him outside of the ring.

8. "The Hangover," 2009

Vastly overrated movie. Not that funny. Said what I said. But Tyson was good in it. In many ways, his scenes made the movie. The overrated movie. The not funny movie.

7. Donovan "Razor" Ruddock, 1991

Tyson and Ruddock fought twice that year. It was again one of those moments when you saw Tyson's raw power. In the second fight, Tyson broke Ruddock's jaw.

6. Foul-mouthed interview, 1999

Tyson did an interview with television journalist Russ Salzberg that shows just how different Tyson was then and now. You see the polished Tyson now. But then, there was no polish. He could be nasty and have no filter. Sometimes, Tyson was so dense that light bent around him. This was one of those times.

5. Mike Tyson returns

Tyson retired from boxing in 2005. Why'd he come back? I mean, why do you think? It's a word that rhymes with cash. The fight against Paul will likely be a word that rhymes with trash. Yet Tyson is doing what he always does: getting us to watch him.

4. Tony Tubbs, 1988

Why is this moment important? It wasn't necessarily one of Tyson's most well known or important fights. Tubbs wasn't exactly a big name. The fight was in Tokyo and the idea was to generate international appeal. Tyson probably didn't need to do that. He was already one of the biggest stars on the planet.

3. Twice bitten, 1997

The second Tyson-Holyfield fight would become one of the most infamous moments in American sports history. Tyson bit Holyfield's ear in the third round and was disqualified.

It reminded people of that ugly side of Tyson. It was so shocking it stunned the boxing world which is saying something.

2. Buster Douglas stuns the world, 1990

It's difficult to put into words how seismic this moment was. Tyson was undefeated and Douglas was a massive underdog. No one, absolutely no one, thought Tyson would lose. It isn't just the greatest upset in boxing history. It's probably a top-five upset in the history of American sports. Douglas knocked Tyson down in the 10th round and Tyson didn't beat the count. Douglas credited his mom with winning the fight. It was a beautiful moment.

1. The creation of the Mike Tyson myth, 1988

Michael Spinks wasn't just a great boxer. At the time, he was already considered one of the best in history. He had similar power as Tyson but was also fast. He was viewed as not just Tyson's equal but perhaps even better. Numerous boxing journalists and insiders picked Spinks to win. Tyson knocked him out in 91 seconds.

That knockout, more than any other moment, created the myth of Tyson as the most feared fighter of all time. It's part of the reason why we'll be watching him fight Paul decades later.

Follow columnist Mike Freeman on social media @mikefreemanNFL