The Ultimate Rap Battle Between Mike Tyson and LL Cool J

Back in the ’80s and ’90s, nobody wanted to mess with Mike Tyson. He was the heavyweight champion of the world, and he was winning all his fights with a thundering knockout.

But that didn’t stop LL Cool J from getting into a feud with the scariest man on the planet. But fortunately for Cool J, it was a rap feud rather than boxing match. Here’s the story of how LL Cool J had some beef with Mike Tyson. 

Mike Tyson performs onstage
Mike Tyson | Donald Kravitz/Getty Images

Mike Tyson’s story of the ’90s

In the 90s, Tyson wasn’t undefeated anymore since he had just lost his first fight ever in his bout against Buster Douglas. And then, a few years later, Tyson was charged and convicted of raping a woman.

He was given a six-year sentence but he only ended up serving three years in prison. After serving his sentence, Tyson returned to the ring and won back his title. 

At this point, he was still at the top of the world. Despite the rape conviction, Tyson was still popular among fans. In fact, when Tyson returned to the ring in 1995 to fight Peter McNeeley, the event sold really well. Tyson himself was also doing really well, as he was getting invitations to a lot of things, including music videos. 

How LL Cool J started feuding with Mike Tyson

According to All Hip Hop, Tyson was hanging out with many of the most famous rappers of the 90s, including Cool J. All Hip Hop said that they seemed to be good friends at the time, but then like many friendships, they grew apart. At this point in time, Cool J started feuding with a rapper named Canibus over a simple tattoo. 

In the song ‘4, 3, 2, 1′, Cool J sneakily talked some trash about Canibus’ tattoo, according to All Hip Hop. Canibus responded by first releasing a song that mocked Cool J and then secretly recording Cool J saying that he was “fearful of an all out battle.”

Then, Canibus, seeing this as a chance for him to become a bigger rapper than Cool J, made a music video with Tyson called ‘2nd Round KO.’ Tyson not only starred in this video, but he even had a few lines.

Cool J didn’t keep his cool. All Hip Hop says that after Canibus’ debut album sold poorly, Cool J came out with his response. The song was called ‘The Ripper Strikes Back’, which is a reference to Cool J’s other nickname, Jack the Ripper. While this song was aimed at Canibus primarily, it also dissed Tyson, too.

Most of what Cool J said about Tyson isn’t really appropriate, but the gist of what Cool J said was that Tyson was a rapist. That is undeniably true, and unsurprisingly, while Cool J traded more shots with Canibus, the feud largely died after this song.

They’re friends again

Because Cool J was primarily feuding with Canibus, he was able to repair his friendship with Tyson. On Tyson’s podcast, ‘Hotboxin’ with Mike Tyson’, Tyson talked with Cool J for about two hours about almost every topic under the sun. 

It’s not clear how the two men reconciled, but it’s clear that they’ve reconciled for a few years now. In fact, Ambrosia for Heads says that, when Cool J was on his podcast, Tyson almost came to tears. 

Apparently, Cool J discovered that he is related to one of the best boxers of all time, Tom Molineaux. Molineaux was a slave boxing champion who fought and beat so many other slaves that he won his freedom, according to Ambrosia for Heads. After hearing about this connection, Tyson said that he was close to crying.