Mike Tyson's incredibly controversial life and career in photos

By Jessica Wedemeyer 10:54am PDT, Aug 28, 2022

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Mike Tyson is one of the greatest boxers in the history of the sport. He's also a major force in Hollywood, with several major film and TV projects under his heavyweight championship belt. On Aug. 25, 2022, Hulu is set to drop "Mike," an unauthorized limited series tracing the ups and downs in the superstar's career and personal life with "Moonlight" star Trevante Rhodes in the title role. The real-life Mike is furious: He told "Entertainment Tonight" that Hulu sees him as just another Black man "on the auction block ready to be sold for their profit without any regard for my worth or my family." He also warned the streamer, "I will always remember this blatant disregard of my dignity." It's the type of drama that tends to surround the retired athlete — who's collaborating with Jamie Foxx, Antoine Fuqua and Martin Scorsese on his own project about his life. To mark the Aug. 25 debut of "Mike," Wonderwall.com is taking a look back at the boxer's controversial life and career in pictures.

Keep reading to relive the highlights from Mike's time in the spotlight — good and bad! — caught on camera…

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A baby-faced Mike Tyson is pictured in an undated photo from early in his career. The champion boxer — who was born on June 30, 1966 — had a rough upbringing in New York City: His mother, whom he's described as abusive, died when he was just 16, and he was estranged from his father. (His biological father's identity remains shrouded in mystery. In his 20s, Mike briefly reconnected with a man who claimed to be his father, but that man died when Mike was 25.) At 12, Mike — who's said he was arrested 40 times before he even entered his teen years, predominantly for stealing so that he could feed himself — landed at the scandal-plagued (but thankfully now-shuttered) Tryon School for Boys, where he learned to box from a former boxer who introduced him to famed boxing manager and trainer Cus D'Amato. Before Mike's mother passed away, she signed over custodial rights to Cus, who became Mike's mentor and surrogate father but died in 1985 when Mike was 19.

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In 1984, Mike Tyson fought Henry Tillman for the opportunity to represent Team USA in the 1984 Summer Olympics. But it wasn't meant to be: He ultimately failed to qualify. He did, however, take home gold medals at the 1981 and 1982 National Junior Olympics.

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Mike Tyson looked ready to rumble during a match in New York City in late 1985 — the year he made his professional boxing debut at 18.

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Mike Tyson is pictured here weighing in before his match against Trevor Berbick — his first title fight — in Las Vegas in late 1986. He won by TKO in the second round, claiming the World Boxing Council heavyweight championship belt at 20 years, four months and 22 days. Mike officially became the youngest fighter to win a heavyweight title — a record he still holds to this day.

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Mike Tyson dated Beverly Johnson for several months in 1986. The boxer and the supermodel, who's more than a decade his senior, were photographed during a night out in New York City around that time. Years later, he dated another iconic supermodel: Naomi Campbell.

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After winning the WBC heavyweight championship belt, Mike Tyson also claimed the World Boxing Association and International Boxing Federation titles. He became the first heavyweight fighter to clinch all three major championships at once, making him the first undisputed heavyweight champion in nearly a decade. (He held the distinction until 1990.) In late 1987, he posed with all three championship belts before a fight in Atlantic City.

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In mid-1988, Mike Tyson celebrated winning the Ring heavyweight championship in Atlanta City with his trainer, Kevin Rooney — who took over training the young fighter after Mike's surrogate father, Cus D'Amato, died. Just months later, Kevin landed in hot water with Mike when he publicly commented on the boxer's personal life. Mike promptly fired him, and Kevin went on to sue the champ for a whopping $49 million for allegedly breaking a verbal agreement that he would serve as Mike's trainer for life. Mike was ultimately ordered to pay his former trainer $4.4 million, though it wasn't the financial blow that had the most impact on Mike: Kevin's departure from Team Tyson marked a major shift in Mike's career, which soon began to plateau. (Mike also fired his long-term manager, Bill Cayton, for similar reasons.)

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Mike Tyson and "Head of the Class" actress Robin Givens held hands as they arrived at the 1988 Emmys in Pasadena, California, six months after they tied the knot following a whirlwind courtship.

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Seven months into their marriage, Mike Tyson and Robin Givens sat down for a joint interview with Barbara Walters for ABC's "20/20." Although things started out strong, with the couple heaping praise upon one another and professing their love for each other, the actress soon admitted that their marriage was "torture," "pure hell" and "worse than anything I could possibly imagine" due to the fighter's "extremely volatile temper," which she described as "frightening." She also claimed that Mike had been diagnosed as manic depressive, though she denied rumors that he'd hit her. "He shakes. He pushes. He swings. Sometimes I think he's trying to scare me," she said. In October 1988 — a week after the interview aired — Robin filed for divorce.

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In 1989, Ohio's Central State University awarded Mike Tyson — who dropped out of high school during his junior year — an honorary doctorate of humane letters.

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In 1990, Buster Douglas knocked out Mike Tyson during a match in Tokyo. It was the first loss of his career.

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In 1991, Mike Tyson posed for a booking photo in Indianapolis following his arrest for sexual assault after 18-year-old Miss Black Rhode Island Desiree Washington accused him of raping her in an Indianapolis hotel room. In early 1992, a jury found him guilty and sentenced him to six years in prison, though he was released on parole in March 1995 after a little less than three years behind bars.

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Mike Tyson's surrogate mother Camille Ewald — the long-term partner of his late trainer, manager and mentor Cus D'Amato — supported the young boxer at court in Indianapolis in January 1992. She reportedly died at 98 in 2001.

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Mike Tyson jumped rope during a training session in Las Vegas in the summer of 1995 — mere days before he returned to the ring following a four-year hiatus from fighting. His first match (against Peter McNeeley) grossed $63 million in the United States, breaking pay-per-view viewership and revenue records in the process. The fight lasted just 89 seconds. Mike went on to win his next three fights.

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In late 1995, Mike Tyson was photographed walking his pet white tiger cub, Kenya, after a workout session in Las Vegas. He kept the big cat for 16 years, he said in 2019, adding that she slept in his bed with him but that he now realizes it was "wrong." He had two other Bengal tigers in addition to Kenya: Storm and Boris.

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In late 1996 and mid-1997, Mike Tyson lost back-to-back matches against Evander Holyfield. The second match — which grossed $100 million and broke pay-per-review records at the time — ended when Mike was disqualified for biting off a chunk of his opponent's ear. (He claimed the move was retaliation for Evander repeatedly headbutting him without penalty.) After the fight — the first heavyweight title fight to end in disqualification in more than 50 years — was called in Evander's favor, a riot broke out in Las Vegas's MGM Grand Garden Arena, leaving several people injured. Ultimately, Mike — who was paid $30 million for the fight, which broke the record for the highest paying professional boxing match — was fined $3 million and forced to take a yearlong break from the sport. (Evander was paid $35 million for the match.)

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A little more than a year after they tied the knot, Mike Tyson posed with second wife Monica Turner on the red carpet at the 1998 World Music Awards in Monaco. They welcomed two children together, Ramsey and Amir, before she filed for divorce in early 2002 amid his infidelity issues. (Mike welcomed his oldest child, daughter Mikey Lorna, with model Kimberly Scarborough following his split from first wife Robin Givens. He later welcomed two more kids, Miguel and Exodus, with girlfriend Sol Xochitl.)

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In 1999, Mike Tyson made his feature film debut in James Toback's ensemble drama "Black and White." He portrayed a version of himself alongside an all-star cast that included Claudia Schiffer, Robert Downey Jr., Brooke Shields, Ben Stiller, Jared Leto, Scott Caan, Bijou Phillips, Gaby Hoffmann and members of the Wu-Tang Clan. He also had small roles as versions of himself in 1999's "Play It to the Bone," 2004's "When Will I Be Loved" and 2006's "Rocky Balboa."

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Mike Tyson landed back in cuffs in early 1999 — a month after he made his return to professional boxing with a controversial match against Francois Botha, whom he ultimately defeated. He was sentenced to a year behind bars and fined $5,000 for assaulting two drivers in a road-rage incident following a three-car traffic accident in Gaithersburg, Maryland, the previous summer. He spent nine months in jail but returned to the ring before the year was through: In late 1999, his match against Orlin Norris was ruled no contest when Mike landed a punch after the bell sounded, rendering his opponent unable to continue with the fight. He won three of his next five matches. As for the other two? Mike tested positive for marijuana immediately following his victory over Andrew Golota, resulting in a no-contest ruling, and Lennox Lewis knocked him out in 2002. (The Tyson-Lennox match broke pay-per-view records at the time, grossing $106.9 million from 1.95 million buys in the United States.)

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In early 2003, Mike Tyson debuted his iconic face tattoo while getting a helping hand from son Miguel during a press conference preceding his fight with Clifford Etienne in Memphis, Tennessee. Mike beat Clifford less than a minute into the first round. It would be his final victory as a professional boxer.

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In August 2003 — the very same month Mike Tyson filed for bankruptcy — the boxer, who was reportedly $23 million in debt at the time, made his red carpet debut as a couple with then-girlfriend Luz Whitney at the Ninth Annual Lady of Soul Awards in Pasadena, California. They dated from late 2002 to early 2004.

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In mid-2005, Mike Tyson lost his final professional boxing match to Kevin McBride when he suddenly quit before the seventh round. A year earlier, he lost to Danny Williams after tearing a ligament in his knee during the first round. He underwent surgery to fix the issue, which had a permanent impact on his abilities in the ring.

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In late 2005, Mike Tyson smooched a pigeon while visiting a breeder in Walsall, England. The boxer famously adores pigeons, which he's kept for most of his life.

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In late 2006, Mike Tyson posed for another booking photo after he was arrested on suspicion of DUI and felony drug possession following a night of hard partying in Scottsdale, Arizona. (He almost crashed into a cop car after leaving a nightclub.) The boxer fessed up to taking drugs that night and checked into rehab a couple months later. In the summer of 2007, he pleaded guilty to the charges against him and was sentenced to just 24 hours in jail. He's had several lesser brushes with the law since then.

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In mid-2008, Mike Tyson's three oldest children — Mikey Lorna, Amir and Ramsey — joined him at the Cannes Film Festival premiere of "Tyson," James Toback's well-reviewed documentary about his life and career.

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In late 2005, Mike Tyson started spending time with British "Big Brother" star Aisleyne Horgan-Wallace. They were photographed sharing a ride after a night of hard partying in London in mid-2008. It's unclear how long they were an item.

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In the spring of 2009, Mike Tyson's non-binary child, Ramsey, held his youngest daughter, Milan, at a special screening of "Tyson" in New York City. The following month, the boxer lost another daughter, Exodus, at 4 following a horrific accident involving a treadmill.

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In mid-2009, Mike Tyson and his third wife, Lakiha Spicer, made their red carpet debut as a couple at the "Fight Night Round 4" launch party in West Hollywood. They tied the knot a few weeks earlier — just 11 days after the boxer lost daughter Exodus with ex-girlfriend Sol Xochitl. (Mike and Lakiha have two children: daughter Milan and son Morocco.)

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Mike Tyson scored a major comeback when he starred as a twisted version of himself in the 2009 comedy "The Hangover" alongside Ed Helms, Zach Galifianakis and Bradley Cooper. He briefly returned for the 2011 sequel and then portrayed versions of himself in "Scary Movie V," "Grudge Match" and the "Entourage" movie.

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In early 2011, Mike Tyson starred on the Animal Planet reality show "Taking on Tyson," which chronicled his involvement in competitive pigeon racing.

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In mid-2011, Mike Tyson and "Rocky" star and creator Sylvester Stallone were inducted into the International Boxing Hall of Fame alongside fighters Julio César Chávez and Kostya Tszyu.

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In early 2013, Mike Tyson was joined by his third wife, Lakiha Spicer, and their two children, Milan and Morocco, plus his oldest daughter, Mikey Lorna, at the Hollywood premiere of "Mike Tyson: Undisputed Truth," a television special centered around his one-man show of the same name. (The show debuted in Las Vegas and had a run on Broadway before the boxer took it on a three-month national tour.) Later that year, he published "Undisputed Truth" as an autobiography that made The New York Times Best Sellers list.

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In early 2013 — after more than 25 years of portraying versions of himself in various film and television projects — Mike Tyson finally flexed his acting chops by taking on a different role: He guest starred as a death row inmate on an episode of "Law & Order: Special Victims Unit." He also popped up on episodes of "Brothers," "Entourage," "Breaking In," "How I Met Your Mother," "Franklin & Bash" and, more recently, "The Last O.G."

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In 2014, Mike Tyson launched the amazingly absurd and surprisingly well-reviewed animated series "Mike Tyson Mysteries" on Cartoon Network's Adult Swim programming block. He voiced a version of himself on the show, which loosely borrows elements from "Scooby-Doo." He posed with co-stars Jim Rash — who voiced a ghost based on the real-life father of modern boxing, the Marquess of Queensberry — and Rachel Ramras — who voiced Mike's fictional adopted daughter, Yung Hee — at San Diego Comic-Con that year. The series ran for four seasons until early 2020.

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A family affair! Mike Tyson and his third wife, Lakiha Spicer, attended the 2018 Nickelodeon Kids' Choice Awards in Los Angeles with the boxer's three youngest children: Milan, Miguel and Morocco. (Miguel's mother is Mike's ex-girlfriend Sol Xochitl.)

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In late 2020, Mike Tyson returned to the ring for the first time in more than a decade for an exhibition boxing match against Roy Jones Jr. The fight, which ended in a draw, was produced by Mike's newly founded Legends Only League. It was the highest-selling pay-per-view event of 2020 and ranked in the top 10 of most-purchased PPV events of all time.

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In late 2021, Mike Tyson brought one of his daughters, Milan, as his date to a fundraising event in Newport Beach, California, for his foundation — Mike Tyson Cares, which will celebrate its 10th anniversary in late 2022 — and We 2 Matter. In recent years, he's focused predominantly on charitable work, launching the Legends Only League and running his cannabis company.