The Five Best Mike Tyson Non Boxing Moments

B. Riley & Co. And Sugar Ray Leonard Foundation's 5th Annual "Big Fighters, Big Cause" Charity Boxing Night

Mike Tyson is best known for his boxing talents and for the numerous memorable fights he had throughout his career. He’s also known as the guy who likes to bit people’s ears off. However, Mike Tyson has had some good moments outside of the boxing ring, where he’s made us laugh, smile, or connect to him in some way that didn’t require him beating the stuffing out of another guy. Here are Mike Tyson’s five best non boxing moments.

His Monster Mash duet with Bobby Brown on Jimmy Kimmel Live! 

Three words: Mike Tyson singing. This came out back in 2005, and it’s still one of the greatest things that Tyson has ever done. Him, combined with Bobby Brown, creates just the right mix of desperate and ridiculous for this video. Their singing together? Awesome. Their dancing? Even better. However, what really makes this video so good and deserving of being on this list are the costumes. Just look at Mike Tyson in the video – he’s dressed like Dracula. How could it possibly get any better than that?

His skit with The Killers’ lead singer, Brandon Flowers

When The Killers won Best International Band at the NME Awards in the United Kingdom (an awards show that has been around for over five decades in the UK) a few years ago, who would have expected that Brandon Flowers, lead singer of The Killers, would have accepted the award through a skit with Mike Tyson at a barber shop. The skit itself is pretty great, with Tyson offering advice to Flowers about not taking too much time off so that your fans forget about you and stealing The Killers’ award by the end of the whole thing. It’s the concept of the whole skit that I love so much though, especially because why would Mike Tyson, with his bald head, need to go a barber shop? And in what world do he and Brandon Flowers go to the same place to get their hair cut?

When he guest starred in an episode of Entourage

Remember when Entourage was the best show ever? It had everything – great jokes, hilarious performances, and the best cameos by the best stars. The first three seasons of Entourage were so good, and then everything pretty much fell apart. Unfortunately for Mike Tyson, he showed up in season seven of the HBO comedy, one of the most forgettable seasons of the show. However, Tyson did make the most out of it, telling Ari that he wanted to star in a show that would be the “black Brady Bunch” and getting offended when Ari made an ear-biting joke.

“Every Little Step” with Wayne Brady

Bobby Brown returns! Well, actually this video doesn’t feature him but the combination of Wayne Brady and Mike Tyson is pretty amazing in its own right. My favorite part about the entire video is just the huge grin that Tyson has on his face for almost the entire time. You can tell how much he’s loving every single second of all the ridiculous dancing that he’s doing. The only thing that would have made it better would have been to have him and Brady sing together.

The Hangover 

The first Hangover movie is a truly stellar comedy, while its two sequels are film abominations that I would put on the same level as the Transformer sequels (if only movie studios could value creativity over making money). One of the best parts of The Hangover is Mike Tyson’s cameo, specifically when he’s first introduced. The guys walk into hotel room to find Tyson sitting at the piano, Phil Collins’ “In the Air Tonight” playing loudly in the background. Tyson gets the gang to sing along with him until the refrain, when he knocks out Zach Galifianakis’ with a mean right hook. Nothing else in the movie comes close to topping it.

Photo by Mark Davis/Getty Images Sugar Ray Leonard Foundation

Chris is a graduate of Saint Joseph's University in Philadelphia, where he majored in English and FIlm. He has been writing for TVOvermind and Uncoached for two years and has written about numerous different television shows and pop culture topics. Contact him through Twitter (@ckinger13)
More articles by