The many lives of Mike Tyson will add another chapter Friday.

At 58 years old, Tyson will fight Jake Paul, the 27-year-old YouTube-star-turned-boxer who wasn’t even born when Tyson’s career was in its prime. It’s Tyson’s first sanctioned professional match since 2005.

The Tyson who will enter the ring at AT&T Stadium in Arlington, Texas, on Friday is a far cry from the Tyson whose pro career ended 19 years ago, when he quit on his stool before the start of the seventh round in a loss to Kevin McBride. He’s an even further cry from the Tyson who infamously bit Evander Holyfield’s ear, the Tyson who spent three years in prison or the “Iron Mike” who dominated the sport in the 1980s.

This Tyson is a shell of the fighter he once was — though he retains the confidence of a championship competitor: “I’m not gonna lose,” he said this week.

MIKE TYSON HITS JAKE PAUL AT THE WEIGH IN #PaulTyson
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LIVE ON NETFLIX
FRIDAY, NOVEMBER 15
8 PM ET | 5 PM PT pic.twitter.com/kFU40jVvk0

— Netflix (@netflix) November 15, 2024

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As Tyson prepares for his comeback against boxing’s viral star of today, his career beckons for a rewind. Here’s a look at Tyson’s evolution by the decade.

The 1980s: The rise of ‘Iron Mike’

At 18 years old, Tyson won his professional debut with a first-round TKO against Hector Mercedes on March 6, 1985 in Albany, N.Y. From there, his rise was meteoric.

Tyson fought 15 times in a 10-month span in 1985, winning all by knockout. He fought 13 more times in 1986, becoming the youngest heavyweight champ in history (at 20 years, 145 days old) with a second round full of vicious left hooks that sent Trevor Berbick — the last fighter to defeat Muhammad Ali — stumbling around the ring.

“I believe sincerely that Mike creates an aura of invincibility,” Tyson’s co-manager at the time, Jim Jacobs, said afterward. “I have watched Trevor Berbick on tapes. And this Trevor Berbick was nothing like the Trevor Berbick I have watched. He fought as if he was in slow motion.”

By Tyson’s 21st birthday, he was 30-0 with the unified WBA and WBC heavyweight titles. In fight No. 31, Tyson defeated Tony Tucker to win the IBF title and become the first heavyweight to hold all three major belts. He went on to defend those belts six more times by the end of the decade — all via knockout. His finish of Michael Spinks, 91 seconds into the first round, is considered by many to be the peak of Tyson’s career.

The numbers for Tyson’s 37 fights in the 1980s were staggering: He won 33 by knockout, and 17 of those in the first round.

The early 1990s: An upset, and a conviction

Tyson was a 42-to-1 favorite and seemingly a safe bet to go to 38-0 when he took on Buster Douglas in February 1990. Instead, the Tokyo Dome was treated to one of the largest upsets in sports history when Douglas knocked him out in the 10th round. Douglas had just been TKOed by Tucker three years earlier and was relegated to the undercard the same night Tyson dominated Spinks.

Behind the scenes, Tyson’s personal life had begun crumbling leading up to the upset. His first wife, actress Robin Givens, said in a televised interview that being married to Tyson was “torture, pure hell,” and filed for divorce, citing spousal abuse. Tyson also split with his manager and trainer ahead of the bout.

After the loss, Tyson rebounded with four wins in 12 months to re-establish his standing and set up a match with heavyweight champ Evander Holyfield, but that fight wouldn’t happen for five years. In 1992, Tyson was convicted of raping an 18-year-old woman and was sentenced to six years in prison. He would serve three before his release on parole in March 1995.

The late 1990s: Tyson vs. Holyfield

Tyson returned to the ring in August 1995 to much fanfare and won back the WBC and WBA titles within 13 months to finally set up the heavyweight clash with Holyfield. But Holyfield, seen as over the hill by 1996, produced a stunning TKO of Tyson in the eleventh round.

A rematch was quickly arranged for June 1997. The highly anticipated Tyson-Holyfield II set a then-PPV record of 1.99 million buys.

Those watching on PPV and inside the MGM Grand saw one of the most bewildering moments in professional sports history. As the third round drew to a close, Tyson grabbed Holyfield multiple times and bit both of Holyfield’s ears, severing part of Holyfield’s right ear and ending the bout with a Tyson disqualification.

Holyfield touching his right ear after being bit by Tyson in their 1997 match. (Photo: Jeff Haynes / AFP via Getty Images)

Tyson’s boxing license in Nevada was later suspended, a ruling followed by other state athletic commissions. It would be over 18 months until the license was reinstated, and it was during that time when Tyson first dipped his toe in pop culture, appearing at WrestleMania XIV.

The decade ended with Tyson returning to the ring to knock out Francois Botha in January 1999 and then serving three and a half months in prison for assaulting two drivers in an incident from 1998, before coming back to fight Orlin Norris in October 1999. That bout was ruled a no contest.

The 2000s: Boxing retirement, pop culture emergence

At 33 years old, Tyson tried to mount a late-career resurgence. After knocking out Lou Savarese in June 2000, Tyson called out heavyweight champ Lennox Lewis, infamously stating, “I want your heart, I want to eat your children.”

His opportunity versus Lewis finally came in June 2002. Lewis largely controlled the fight, as the champion survived Tyson’s round one onslaught and controlled the pace with strong jabs. With less than a minute left in the eighth round, a Lewis right cross landed flush and put Tyson on his back for the count.

The loss accelerated the end of Tyson’s professional career. His last pro win came against Clifford Etienne in 2003.

His final professional bout — until Friday’s against Paul — came against McBride in 2005. Tyson, who struggled mightily with his stamina and the height difference, managed to keep the fight close on the scorecards, but then was issued a two-point penalty for head butting. The sixth round ended with Tyson slumped on the mat after a slip, and the match ended without Tyson ever getting off his stool to answer the seventh round.

“I do not have the guts to be in this sport anymore,” Tyson said afterward. “I don’t want to disrespect the sport that I love. My heart is not into this anymore. I’m sorry for the fans who paid for this. I wish I could have done better.”

Tyson on the mat after slipping at the end of the sixth round versus McBride. Tyson would quit the bout before the start of the seventh. (Photo: Paul J. Richards / AFP via Getty Images)

Within a few years, Tyson found a second career — through movies, television and entertainment.

He made an appearance in the movie “Rocky Balboa” in 2006, but his breakout moment came in “The Hangover” in 2009, when he air drummed to Phil Collins’ “In the Air Tonight” before knocking out Zach Galifianakis’ character, Alan. He later made cameos on “How I Met Your Mother,” “Dancing with the Stars” and in a Foot Locker commercial in which he apologizes to Holyfield for biting his ear and embraces his old rival.

The 2020s: A return to the ring

In 2020, Tyson agreed to battle Roy Jones Jr. in an eight-round exhibition, a bout sanctioned in California. Both boxers were over 50, and the match was competed under specific instructions that it should not go beyond “the boundaries of a competitive boxing exhibition,” meaning neither opponent should attempt to knock the other out.

The fight was scored a split draw despite Tyson significantly outlanding Jones. On the same card, Paul appeared in his second boxing match, knocking out former NBA player Nate Robinson.

Netflix announced Friday’s Tyson-Paul bout in March 2024. It was initially supposed to take place in July. In April, the bout was sanctioned by the Texas Department of Licensing and Regulations to be a professional fight consisting of eight two-minute rounds fought with 14-ounce gloves.

In late May, Tyson suffered an ulcer flareup while flying from Miami to Los Angeles, forcing the fight to be delayed. According to Tyson, the ulcer was over two inches large in his stomach and resulted in him losing 26 pounds. On the flight, he said he threw up blood.

“I asked the doctor, ‘Am I going to die?’” Tyson said in the preview series, “Countdown: Paul vs. Tyson.” “And she didn’t say no. She said we have options, though. That’s when I got nervous.”

Required reading

(Photo: Timothy A. Clary / AFP via Getty Images)