Mike Tyson

Mike Tyson's Biggest Regret: Not Smoking Weed with Tupac

| by Alex Groberman

As part of a recent ESPN special examining his relationship with Tupac Shakur, Mike Tyson says his biggest regret was not smoking weed with deceased rapper.

Not his conviction for rape. Not his ill-advised face tattoo. Not the whole ear-biting fiasco. Nope, Tyson's biggest regret was not blazing up with a rapper.

The strange revelation came as Tyson recently reflected on his friendship with the controversial figure who was gunned down in 1996.

"He always wanted me to smoke weed with him, and I never did it, and I wish I did," Tyson said.

According to Tyson, he declined Tupac’s offer because he was a closet smoker and didn’t want it revealed to the general public that he smoked marijuana. The duo’s friendship is the subject of an ESPN documentary that aired Tuesday.

Among other interesting topics of the pair’s friendship were:

-       Tyson’s description of Tupac’s last moments: "He didn't last long, but the time he did last, every minute, every tenth of a moment was explosive," Tyson said.

-       On their relationship when he went to prison for rape in 1992: "Every day, he would call me or get a chance to call me or send a message," said Tyson. "He would get word to me in prison."

-       The similarities that the two men shared: "Our problem was we always had to worry about someone betraying us, our closest friends," Tyson said.

-       That Tupac became angry when Tyson selected another rapper's song as his fight intro music: "He said, 'Don't you ever play those (expletive) songs again, they don't give a (expletive) about you,'" Tyson recalled. "When he said that, it pierced my soul. ... I felt like I did something wrong."

-       On being responsible for Tupac’s death: "I felt extremely guilty because I felt if he didn't come to this fight, that would have never have happened," he said. "It's just so crazy that we had talked every day for a week."