Tyson reminisces about relationship with Tupac

When Mike Tyson looks back on his friendship with Tupac Shakur, he thinks about the rapper's big heart, explosive anger — and the one regret he has about their relationship.

"He always wanted me to smoke weed [marijuana] with him, and I never did it, and I wish I did," Tyson said in a recent phone interview. Tyson declined because he was a closet smoker and didn't want it to get out that he smoked the drug. Now, when he looks back on the lost opportunity, he says: "That's my biggest regret."

Tyson's friendship with Shakur is the subject of a new documentary, One Night in Vegas: Tyson & Tupac.

The 25-year-old rapper was shot after a Tyson fight in Las Vegas on September 7, 1996. He died six days later.

The documentary chronicles their relationship, which Tyson said took hold when he was imprisoned in 1992 for rape. "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."

By the time Tyson was released in 1995, Shakur would be jailed for sex abuse. When he got out of prison, Tyson and Shakur's friendship deepened. Both found it difficult to find people who truly cared for them, Tyson said.

Friendship was so important to Shakur that he criticised Tyson when he selected a song from rapper Redman as his intro music at a fight. After that talk, Tyson decided Shakur's raps would be his intro music for life.

It was partly because Tyson had chosen his music that Shakur went to Tyson's fight in Las Vegas. He made a special rap for Tyson's big night. After the fight, which Tyson won by knockout, Shakur was to join Tyson at a victory party. But he never made it.