The Interview That Left Mike Tyson In Tears

Did you know an interview once left Mike Tyson in tears? And no, it wasn't upon recalling how he punched Zach Galifianakis' character in "The Hangover".

Boxing superstar Tyson is arguably one of the most famous and... complicated athletes in history. He first made his professional debut at the age of 18 in 1985. By 1986, he was crowned the youngest heavyweight champion in the history of boxing, and reigned as its undisputed champ until 1990. As ESPN wrote, "Tyson landed 56 percent of his power punches, which is 15 percentage points higher than the heavyweight average." Ouch, literally. Whether it be his professional statistics, his facial tattoo, or his infamous incidents in the ring (we won't bite—err talk your ear off about it), he's a tough cookie. But that was then, this is now — we guess?

These days, Mike Tyson has softened up and gotten more real and in-touch with his (perhaps) bottled-up emotions during his best years. The star certainly is not perfect, and his track record of domestic abuse towards ex-wife Robin Givens (via Complex) could tell you that. But he has gone on to give the world 100-percent of Mike Tyson. The star put on a one-man show, Undisputed Truth, per The Guardian, that made it to Broadway and has remained in the spotlight. The splashy boxer definitely still has reflecting to do, but he's not going anywhere, and he's sharing his feelings. 

For example, here's an instance where Mike Tyson actually broke down crying in an interview. 

Mike Tyson teared up over this friend

So, what interview led the tough Mike Tyson to break down in tears? The famously hard-boiled star has definitely let his guard down recently, specifically, on his podcast, "Hotboxin' with Mike Tyson". 

During his chat with Sugar Ray Leonard in May 2020, Tyson teared up explaining what the boxing legend meant to him, and how he even watched Leonard's fights in juvenile detention. "I saw you fight Wilfred Benitez when I was locked up, what was that, in '79?" Tyson asked, holding back tears. "I can't even talk." After Leonard told Tyson that he cares for him, the former heavyweight champion interrupted him. "I saw you fight Duran, and it changed my life. I said, 'this is what I'm going to be,'" Tyson added. "You might not think you're nobody... but I love you," he added.

Later in his chat with Leonard, Tyson also discussed his general love of the sport. "I read about them all. I studied them all. I know the art of fighting, I know the art of war, that's all I ever studied. That's why I'm so feared, that's why they feared me when I was in the ring," he said. "I was an annihilator. It's all I was born for. Now those days are gone. It's empty. I'm nothing. I'm working on the art of humbleness. That's the reason why I'm crying, 'cause I'm not that person no more, and I miss him."

We see you, vulnerable Mike Tyson! 

Mike Tyson welcomed back Sugar Ray Leonard

Sugar Ray Leonard appeared on "Hotboxin' with Mike Tyson" again in April 2021 alongside fellow legends Thomas Hearns and Shane Mosley. There was much teasing to be had between the group as Mike Tyson pulled up highlights of the controversial Hearns vs. Leonard II match from 1989. Watching the punches decades later must have reignited the competitive spirit between the two, as when talking about staying composed in the ring and placing shots, Hearns asked Leonard, "you wanna place it right here," while stroking the side of his face.

Hearns stated Leonard was scared in their match, but his opponent was quick to disagree. "I wasn't scared, I was concerned," he replied. With some more teasing mumbling from Hearns, Leonard threw down the gauntlet: "Tommy, I can knock you out now." Tyson's response to the legends was a taken aback "holy s***" and he tried to stop them from getting into it, all the while laughing with Mosley at the entertaining size-up.

The pair stood up and aimed fists at each other's chins while rasping some hype talk before lightly acting out some punches. Leonard took a seat first, but Hearns was still fired up claiming whenever they fight again, he would be the dominant force. Tyson took over the moment and made the group fall into laughter. In September 2021, Leonard admitted to Hearns being the rightful victor of their 1989 match, revealing a friendly relationship that is all about riling each other up. Who knows what the legends could have gotten up to without Tyson in the room.