By the time you get through this list, you will probably agree that there may not be a celebrity whose life is more interesting than that of Mike Tyson. As a youth, Tyson dropped out of school due to bullying. He was then arrested over 30 times as he desperately sought out approval from the streets. But at the end of one of those arrests, came the opportunity for Tyson to start boxing. And as you definitely know, Mike Tyson was one hell of a boxer. He is arguably one of the greatest of all time and Tyson’s time in the ring, at least at his peak, was nothing short of domination.
But as you’re going to learn, there was more than meets the eye when it came to the Champ. You know he’s won championships, but do you know what STD he was struggling with during his biggest match? You may assume someone like Tyson got ‘intimate’ often but did you know he arguably slept with more women when he was in jail for rape charges than when he was free? And of course, you know Tyson has that tattoo, but do you know what he originally wanted on his face?
This list will cover it all, ranging from his marriage to Robin Givens that culminated in her stating on live television she was living in hell, to his relationship with Naomi Campbell (that started out with a hookup in an unusual place), to the role Brad Pitt, Tupac and Joan Jett have all had in his life. There are no shortage of interesting, albeit sometimes controversial tidbits about Iron Mike. There was even a time where he attacked fans and another where he attacked several prostitutes.
Have a friend that’s a fan of Mike Tyson or may want to learn more about arguably the most controversial boxer of all time? Feel free to share the list on social media.
20. What His Tattoo Was Going To Be
It was back in 2003 that Mike Tyson stepped out and announced to the world that he had decided to have a tribal design tattooed onto his face. While I think we can all agree this was a pretty outrageous look, do you really have the confidence to go up to Iron Mike and tell him otherwise?
One person that was able to stand up to Tyson was his tattoo artist, and you’ll probably be pretty glad he did. When talking with In Depth with Graham Bensinger, Tyson admitted that “I was going to be the Man of Hearts, baby…I was very close to doing it but the tattooist said, ‘I ain’t doing that.’”
What Tyson means by that, is that he was going to get little hearts tattooed onto his face because he thought it would look so cool.
When talking about his tattoo in 2015, Tyson reaffirmed that he was glad he got the tattoo and that over one million people have a very similar tattoo now, so maybe he was happy that he didn’t become Heart Man.
19. He Had Gonorrhea
There was no doubt that when Tyson first started out his boxing career, he had everything it takes to be the greatest of all time. In 1986, Mike Tyson was facing off against Trevor Berbick for the WBC Heavyweight Championship. Tyson was 27-0 at the time and made quick work of the champion, winning the match early on in the 2nd round. Tyson was only 20 years old when he won the fight, making him the youngest champion in boxing history (he was also 12 years younger than Berbick).
While you may have known that above piece of trivia, what is even more obscure is that years later Mike Tyson admitted that he was suffering from gonorrhea, and in his words, was “burning like a Good Humor in July.”
18. How Rich, and Broke He Got
Mike Tyson made a ton of money during his career. In fact, in 1990, Mike was the highest paid athlete that year, earning $28.6 million. Over his entire career, Tyson earned somewhere between $300 and $400 million. But as great as he was in the ring, he was equally great at blowing through his money. It was announced in late 2003 that Tyson was filing for bankruptcy. A problem he got himself into largely due to an extreme amount of debt owed in taxes. It also doesn’t help that he owned several exotic pets, most notably his tigers.
While Tyson has been able to get himself back on his feet, in large part due to roles and appearances in films like The Hangover and other projects outlined below, he’s definitely a celebrity who has been through it all.
17. His Run-In With Brad Pitt
Mike Tyson had a very public and messy divorce with his wife, Robin Givens. After the divorce, the two would still spend time together and in Tyson’s memoir he wrote about an incident where he decided to show up to her house unannounced. Tyson came upon Givens sitting with none other than Brad Pitt! I cannot imagine an ex-husband that you would want to run into less than Mike Tyson.
Tyson wrote that Pitt “looked ready to receive his last rites” and was visibly stoned at the time, also pleading “dude, don’t strike me, don’t strike me. We were just going over some lines. She was talking about you the whole time.”
Perhaps Pitt was realizing that Tyson had the ability to drastically alter his acting career with one swing to the face. Thankfully Tyson was in an understanding mood and allegedly left the two to be alone.
16. His Lowest Point
As you’re going to continue to learn as you read through this list, there were several periods of Mike Tyson’s life that you might consider to be low points. When asked by an interviewer what his worst moment was, you may be blown away.
“I’ve got seven women there, and I have a morphine drip, and I had my cocaine, and I had my Cialis, I had my marijuana, I had the Hennessy, and I am at my lowest point because I got paranoid and I thought these women were trying to rob me and set me up. I started beating them. I was in a dark place.”
15. Why He First Fought
Mike Tyson has made it clear in several interviews in the past that he is a huge fan of pigeons. He claims the bird gives him a great sense of calm and recalled a story from his youth in which he felt insecure and judged by everyone, but the birds never judged him and gave him a feeling of importance. So much so, that Tyson’s first ever fight came because of his love of pigeons.
“When a bully that was antagonizing me killed one of my birds in front of me, I snapped and began fighting him. If it weren’t for this guy hurting my beloved animal, I may not have ever had the desire to fight. By him hurting an innocent being that I loved and cherished, it was the catalyst to the fighter within.”
While Tyson’s love of pigeons is definitely a little unusual, there’s nothing wrong with finding a deep connection and love with an animal. Given that he’s been a man who’s had some rage issues in the past, I’m sure anything that is deemed “calming” would be a win!
14. His Marriage With Robin Givens
Mike Tyson has been married 3 times in his life, but the first one happened in February, 1988, and within one year, the relationship was headed for divorce. His wife, Robin Givens, was an actress, but it was clear from the start that this was not a healthy relationship.
Givens admitted years later that there was an incident prior to their marriage where Tyson hit her, but that she forgave him because she thought he could change. The peak of their downfall may have come when the two appeared on an interview with Barbara Walters, in which Givens described her relationship with Tyson.
“Torture. It’s been pure hell. It’s been worse than anything I could possibly imagine… He shakes. He pushes. He swings. He — sometimes I think he’s trying to scare me. There — there’s — there’s — there are times when — or there were times when it happened when I thought that I could handle it.”
Givens admitted that Tyson beat her a few days after the program aired and the two filed for divorce under 2 months later.
13. Drederick Tatum
Drederick Tatum was one of the best small time characters that The Simpsons has ever had. Voiced by Hank Azaria, the character is a direct parody of Iron Mike. This includes sounding the same, looking similar, having a similar backstory (including being a gold medalist) and having a brutal criminal past. Drederick is also managed by ‘Lucius Sweet’ who is a direct parody of Tyson’s former manager, Don King (much more on him below).
When Tyson was asked his thoughts on the character in an interview, he stated,
“I wasn’t aware of him until somebody told me. I didn’t pay it much attention, but I’m used to people making cartoon characters of me so I’ve never seen it as offensive. I’m not some superhero, I’m just an entertainer.”
12. His Sexual Prowess
As you’ve learned, prior to winning the Heavyweight title Mike Tyson was battling himself a nice STD. Not too surprising considering that in his memoir he wrote his main requirement for sleeping with a woman was that she was breathing! Tyson admitted that he would often have sex while wearing the championship belt, and would also record the sexual acts. When Tyson was sentenced to prison on a sexual assault charge, which we’ll detail below, he reportedly smuggled different women into the jail on a regular basis for some personal time. He apparently got so popular that when Rory Holloway, a former manager and long-term friend of Tyson went to visit him in jail, he had to sleep in the parking lot because there was such a long line of women waiting to meet with the Champ. Rory speaks more to the extent of Tyson’s sexual addiction below, including his thoughts on how it prevented him from being the best ever.
If that didn’t make him sound sexually active enough, also while in jail, he even reportedly had an affair with his substance abuse counselor that lasted several months. Call me crazy but I’m pretty sure that’s a breach of patient rights!
11. The Circumstances Of The Buster Douglas Fight
One thing you need to understand is that going into Tyson’s fight with Buster Douglas in 1990, Mike Tyson was easily considered to be one of the top boxers in the world. His last match lasted only 91 seconds, he had never lost, and he was a 42/1 favorite for the fight. But as you are about to learn, Buster Douglas pulled off what is considered to be one of the greatest upsets in sports history.
Not only did Buster survive the onslaught of Mike Tyson, but 35 seconds into the 10th round, it was Tyson that was sent barrelling into the mat for the knockout blow. It was the first time Tyson had ever been knocked out.
Buster was allegedly riding an emotional high after losing his Mother earlier that month, but there was still nobody that would have seen this result coming. Tyson admitted years later that while he was physically in shape for the fight, he was perhaps not as mentally strong as he had hoped.
As a fun twist, Joan Jett (yes, the famous musician) used to be Mike Tyson’s wake-up call on fight days, but was unable to do it on the day of the Buster fight. So essentially what we’re saying is it was all Jett’s fault!
10. The ‘Desiree Washington’ Incident
Mike Tyson’s legacy was forever shifted in July, 1991, when he was arrested for the alleged rape of Desiree Washington, who was the recent Miss Black Rhode Island and was only 18 years old at the time (Tyson was 25). Washington claimed to investigators that Tyson invited her to his hotel room late at night and that after she denied his sexual advances, Tyson pinned her down and sexually assaulted her.
Tyson was hostile during questioning, as well as during the trial, leading some people to feel the jury judged him more based on his character of being arrogant and brutish than on the overall level of evidence present.
Tyson was sentenced to six years in prison and four years of probation but was released in 1995 after serving less than three years. Tyson’s first fight back after prison was against Peter McNeeley, but Tyson demolished him and the fight only lasted 89 seconds.
9. He Did Drugs With Steve-O
When it comes to people in Hollywood that would be absolutely crazy to party with, a pre-sober Mike Tyson and Steve-O need to be pretty high up on your list. I mean at least if you want to get into shenanigans that are going to be memorable, even if not for all the right reasons. While this is a story told from Steve-O’s perspective, he talked in an interview about a night out with Iron Mike.
“We spent three hours locked in a bathroom together. There was this house party in the Hollywood Hills. And I remember I was distinctly not invited, but I showed up and rang the doorbell. Mike Tyson opened up the door. I said, “Hey, is it cool if I come in?” And he said, “You got any coke?” And I told him, “Yeah, dude, I got a bunch.” And I did. I had like a whole eight ball in one pocket, half an eight ball in the other pocket.”
The two allegedly sat and talked about racism and different “deeper matters” of the world. Or at least they like to think they did.
8. The Ear Incident
There are a lot of famous moments in Tyson’s in-ring career, but the biggest might be the infamous “Bite Fight” between Tyson and Holyfield on June 28th, 1997. The two had previously fought, with Holyfield winning, so Tyson definitely had anger and revenge on his mind that night, but the match came to an end in the 3rd round when Tyson bit off part of Holyfield’s ear. He later admitted to Oprah that the reason was because he was so pissed off that Evander was such an amazing fighter. As well as this, Tyson felt that Holyfield had used a lot of headbutts during their first fight, and was starting to utilize this tactic again.
Tyson had his boxing license revoked by the Nevada State Athletic Commission and was fined $3 million for the incident. The ban ended up not being permanent and a little over a year later it was overturned allowing Tyson to return to boxing. Tyson and Holyfield have since been able to reconcile and become close friends.
As a fun fact, Tyson went on to accept a role to be a guest referee at the upcoming WrestleMania. The reasoning? Vince said that he would pay him $3 million for the appearance.
7. Why He Hates Don King
Don King was the longtime promoter for Mike Tyson, but their relationship was anything but friendly. In Tyson’s book, he verbally attacked King throughout it, at one point calling him “a slimy reptilian motherfu****.” Tyson claims that Don King charged him, and stole upwards of $50 million from him throughout his career. Their feud may have come to a peak one day when they were out in Florida, as Tyson explains.
“Don picked us up at the private airport in his Rolls. We were driving down to Miami from Fort Lauderdale on the I-95. Don said some innocuous thing and all that jealousy and rage spilled out of me and I kicked him in his fucking head.”
6. His Role In Tupac’s Death
Mike Tyson made friends with a lot of influential people during his time in the spotlight, one of whom just happened to be Tupac. The musician had become friends with Tyson after visiting Tyson when he was in jail serving time for his rape charges.
It was their friendship that probably caused Tupac to decide to go to the boxing match between Bruce Seldon and Mike Tyson. It ended up being one of the shortest matches Heavyweight Championship fights in boxing history, lasting only 1:49 as Tyson dominated.
Following the match, Tupac and his entourage got into an argument with Orlando “Baby Lane” Anderson, in the lobby following the fight. The two had a previous history and it was later that night that Tupac was shot and killed in a drive-by shooting. Tupac was only 25 years old at the time of his death, but he still remains one of the most influential musicians of all time.
5. One Man Show
Mike Tyson has accomplished a lot of things in his life, but none may be more shocking than the fact that he’s hosted a successful one-man show for several years now. The show, Undisputed Truth, is what Tyson described as “scripted freestyle, that’s what it is. Can you do that? We’ll do that. I’ve been getting used to coming off the script and talking from the heart. After four years, I need to keep it fresh.”
The performance, as described by MGM Grand, promises that Tyson “thrills audiences with tales of victory, tragedy and redemption. Tyson delivers captivating vignettes from his life, experiences as a professional athlete and controversies in between.”
Tyson has performed the show all around the world, including Paris, Australia, on Broadway and too many nights performing in Vegas to count. There are many people out there that feel Tyson is nothing more than a dummy, but performing a one-man show is not only incredibly exhausting, it must be nerve wracking. Especially when his story has had as many rough spots as his has.
4. Mike Tyson Mysteries
Mike Tyson has done a lot of things in his life that people would consider to be unusual. One thing that may be at the top of the list is the fact that he stars in his own television show, Mike Tyson Mysteries. The show follows a similar theme to Scooby-Doo! and Johnny Quest and follows Mike Tyson, his 18-year-old adopted daughter, the ghost of the Marquess of Queensberry and a pigeon (voiced by Norm Macdonald) as they go around trying and solve mysteries.
While the storyline will not always solve the mystery, are you ever going to consider watching Norm Macdonald being a pigeon as a waste of time? As of now there have been 2 seasons, and 30 episodes total for the series. However, when Tyson was first approached with the project, he turned it down.
“I thought it was going to be like the first Edison photo movie, click, click, click…You know, you take the books and flip the pages, and then I saw the first draft. It was pretty much up-to-date, very sophisticated, and I said ‘Yeah, I want to try and do this and make it look good.'”
3. His Daughter Passed Away
Mike Tyson is the father of 8 children, but he tragically saw one of his daughters pass away when she was only 4 years old. Exodus Tyson was found in critical condition after her neck became caught in the cable of a treadmill exercise machine.
When talking about the importance of his marriage and family, Tyson opened up saying “If I wasn’t married I’d be very different. I’d still be that violent schmuck because that’s all I once knew – how to hurt people. I used to do all that stuff and I never cared about the repercussions. But I’ve surrendered now. I was thinking of my daughter when …[he points to his teary gaze] … but I’m just happy I’m not that same person.”
2. He Beat Up His Fans
When it comes to being a successful celebrity, one thing that you probably want to make sure you don’t do is beat up on the paparazzi, or even worse, your adoring fan base. In Tyson’s autobiography, he goes over several incidents where he physically went after fans that he thought were being too aggressive.
This included an incident in 2003, where he says, “If I wasn’t on coke, probably nothing would have happened. But I was, so I chased them into the lobby and up the escalator. We got to the top of the escalator and I knocked one of them out with one punch…The other guy was hiding behind the front desk and I pulled him out and hit him. He was spared when hotel security came.”
1. The Extent Of His Addictions
As you’ve read in several stories above, Mike Tyson was definitely no stranger to using illegal substances. This not only cost him millions of dollars but after he retired from boxing in 2005 his addictions continued to get more serious. He admitted that at one point he weighed over 350 pounds, and had a diet that was consisting of ice cream, Oreos and alcohol.
While fighting, Rory Holloway stated in an interview that “the only reason he may not go down as the best is because of his weakness for women. Every decision he made was around women and sex.” At one point, Rory was employing 24 hour bodyguards to try and prevent Tyson from sneaking out and getting intimate.
Want to know just how smooth Iron Mike was? How about the fact that he met Naomi Campbell at a party, and then according to Rory “Mike says he’s got to use the restroom. Next thing, Naomi’s following him and I’m outside holding their drinks. Guests are walking up and I’m telling them, ‘Bathroom’s taken.”
Tyson wrote in his book that “I’m a vicious addict and, if I don’t follow my steps, I’m going to die.”
In 2006, he was arrested after driving home drunk from a bar while also on cocaine. There was also the incident in 2000 when Tyson tested positive for cannabis use prior to his fight with Andrew Golota. He said in interviews that he used to use a fake penis to try and bypass drug tests, but on that day, the person who was in charge of his ‘whizzer’ was not there. Talk about letting the team down.
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