Tyson regained one belt by easily winning the WBC title against Frank Bruno in March 1996. It was the second fight between the two, and Tyson knocked out Bruno in the third round. In 1996, Lennox Lewis turned down a $13.5 million guarantee to fight Tyson. This would've been Lewis's highest fight purse to date. Lewis then accepted $4 million from Don King to step aside and allow Tyson to fight Bruce Seldon for an expected $30 million instead with the intention that if Tyson defeated Seldon, he would fight Lewis next. Tyson added the WBA belt by defeating champion Seldon in the first round in September that year. Seldon was severely criticized and mocked in the popular press for seemingly collapsing to innocuous punches from Tyson.

In 2000 Tyson dismissed everyone who was working for him and enlisted new accountants, who prepared a statement showing he started the year $3.3 million in debt but earned $65.7 million. In August 2007, Tyson pleaded guilty to drug possession and driving under the influence in an Arizona court, which stemmed from an arrest in December where authorities said Tyson, who has a long history of legal contentions, admitted to using cocaine that day and to being addicted to the drug.

8. "On occasion we need to make a second effort – and a third effort, and a fourth effort, and as many degrees of effort as may be required to accomplish what we strive to achieve." – Thomas S. Monson

In 2000 Tyson dismissed everyone who was working for him and enlisted new accountants, who prepared a statement showing he started the year $3.3 million in debt but earned $65.7 million. In August 2007, Tyson pleaded guilty to drug possession and driving under the influence in an Arizona court, which stemmed from an arrest in December where authorities said Tyson, who has a long history of legal contentions, admitted to using cocaine that day and to being addicted to the drug.

In 1992, Tyson was convicted of rape and sentenced to six years in prison. He was released on parole after three years. After his release in 1995, he engaged in a series of comeback fights, regaining the WBA and WBC titles in 1996 to join Floyd Patterson, Muhammad Ali, Tim Witherspoon, Evander Holyfield and George Foreman as the only men in boxing history to have regained a heavyweight championship after losing it. After being stripped of the WBC title in the same year, Tyson lost the WBA title to Evander Holyfield by an eleventh round stoppage. Their 1997 rematch ended when Tyson was disqualified for biting Holyfield's ears, one bite notoriously being strong enough to remove a portion of his right ear. In 2002, Tyson fought for the world heavyweight title, losing by knockout to Lennox Lewis.

Auch Tysons neuer Trainer Aaron Snowell, der zum ersten Mal mit Tyson zusammenarbeitete, wirkte unprofessionell: Tysons schwere Schwellung über dem linken Auge wurde erst spät gekühlt, und nur mit Eiswürfeln statt mit dem Kühleisen.

Silver screen legend Olivia de Havilland, for example, sued FX Studios for briefly depicting her in a miniseries about Hollywood rivals Bette Davis and Joan Crawford. She won at trial, though an appeals court reversed her victory, citing the producers’ First Amendment rights.

Despite this loss, Tyson continued to storm through the heavyweight division. One year after D’Amato’s death, Tyson became the youngest heavyweight champion ever when he gained the World Boxing Council (WBC) championship belt after a two-round knockout of Trevor Berbick. Co-Manager Jimmy Jacobs told Pat Putnam of Sports Illustrated that everything was going to plan: "Cus predicted that Mike would fight for the title before the end of 1986…Cus said the only way to prepare Mike for this was to give him a speed education by a multiple of four. So there has been no R and R for mike tyson boxing life. There couldn’t be. And he has held up beautifully." The next year he united the heavyweight championship, defeating James "Bonecrusher" Smith for the World Boxing Association (WBA) belt in March and Tony Tucker for the International Boxing Federation (IBF) belt in August. Tyson was on top of the boxing world as the most ferocious boxer in the sport’s most glamorous division. But he soon learned that success often comes at a price.

In January 2017, Tyson launched his YouTube channel with Shots Studios, a comedy video and comedy music production company with young digital stars like Lele Pons and Rudy Mancuso. Tyson's channel includes parody music videos and comedy sketches.

In November 2013, Tyson stated "the more I look into the churches and mosques for god, the more I start seeing the devil". But, just a month later, in a December 2013 interview with Fox News, Tyson said that he is very grateful to be a Muslim and that he needs Allah in his life. In the same interview Tyson talked about his progress with sobriety and how being in the company of good people has made him want to be a better and more humble person.

The ironic thing about what followed is that Tyson was enjoying his best moments of the fight. The former champ flew at Holyfield with a powerful combination and also landed a pair of left hooks and a big right hand. Undeterred, Holyfield backed his man off with the jab, but when the fighters drifted inside, the heads touched again and all hell broke loose.