To stump Jamie Foxx? That takes a lot of work. But Mike Tyson pulled it off. The two celebrities have been connected for nearly 30 years, the boxer being a frequent and willing muse for Foxx. But recently they were discussing the actor’s long-anticipated, Martin Scorsese-directed biopic of the mercurial pugilist.

During the conversation, Tyson, who finished his career with 50 wins (44 by knockout) and six losses, looked to be in pure bliss. But how could a man once worth $300 million, who went bankrupt for many reasons (likely including legendary splurges and Don King’s crippling influence) find happiness in such straits? “Nobody can take anything from me anymore,” is what Foxx said Tyson told him. “I’m happy. I don’t have any money. I don’t have any devils. I don’t have any demons.” And he has said as much before.

Tyson, today, is a married father of eight. He’s a motivational speaker, actor and author. A man who, in his 50s, lives in the suburbs and is guided far more by experience than the flash, intimidation, controversy, violence and recklessness that defined his 20s. “I didn’t think,” he admitted last year, “I’d make it through my 30s.”

Twenty-three summers ago, the biggest story in sports, and one of the biggest stories in America, was the comeback of Mike Tyson. He’d served three years in an Indiana prison after being convicted of the 1991 rape of then-18-year-old Miss Black Rhode Island Desiree Washington. It’s a crime he denied then, as well as now. It’s one he says he’ll never apologize for.

The crime has followed Tyson even as he has attempted to redeem himself (some say the boxer has been chasing redemption since he was a very young man, for varying reasons). How does one commemorate, or even think about, the moral labyrinth that is Tyson?

And when he was released from prison, again a free man, excitement about the former champ’s return reverberated in the boxing community, and among some in black communities. But could Mike Tyson return to the form that made him the youngest heavyweight champion in boxing history, the man who won 12 of his first 19 fights via first-round knockout and the first heavyweight to hold and unify the WBA, WBC and IBF titles? Would he be able to adjust to the world around him? And would society, given the nature of his conviction, welcome him? All this was is play. And it’s not like Tyson was even the sole cultural or sports headline of the wild summer of ’95.

Real sick, raw nights / I perform like Mike / Anyone — Tyson, Jordan, Jackson …

— The Notorious B.I.G., “Victory” (1997)

Nineteen ninety-five was actually the Year of Mike. “Scream,” Michael Jackson’s duet with his sister Janet, took aim at the press, with whom Michael Jackson had a long-standing and difficult relationship. Tensions boiled over during the 1993 coverage of Jackson’s eventually dismissed child sexual abuse case. “Scream” — Just stop pressurin’ me / Stop pressurin’ me / Make me wanna scream — was seen by many as The King of Pop’s official clapback and Janet’s way of riding for her big brother.

Across the Mike spectrum, Michael Jordan’s return to basketball that March, a week before Tyson’s release from prison, made international waves. But it was during the summer of 1995, while filming Space Jam, that Jordan’s obsession with the game of basketball went to another level.

So incensed with losing in the playoffs that spring to Shaquille O’Neal, Penny Hardaway and the Orlando Magic, his second and final postseason defeat of the ’90s, the Chicago Bulls megastar had a specifically designed “Jordan Dome” constructed. In it, Jordan, along with pros like Cedric Ceballos, Juwan Howard, Grant Hill, Dennis Rodman and members of the NCAA champion UCLA Bruins would play high-intensity pickup games every night after Jordan finished filming. These celebrity scrimmages, a cultural forefather to the modern-day obsession with offseason basketball, helped propel the Bulls to a then-record 72-10 season.

A jovial question was very often, “You gettin’ the Tyson fight this weekend?”

Pop culture was simultaneously reeling and evolving. The Model T of reality TV shows was the most captivating program in America in 1995: the O.J. Simpson trial. A month before Tyson’s first post-prison bout, a small company named Amazon sold its first book. And two weeks after the fight, an online auction site dubbed AuctionWeb got off the ground. It’s known today as eBay. The deaths of the Grateful Dead’s Jerry Garcia, Yankees legend Mickey Mantle and the voice of American sports (aka Howard Cosell), as well as the early deaths of Selena and Eazy-E all occurred prior to Tyson’s Aug. 19 return to the ring.

And the summer of 1995 was soundtracked by TLC. Their sophomore CrazySexyCool featured the monster singles “Diggin’ On You,” “Creep” and the uber-seductive “Red Light Special.” The group’s defining record, though, was “Waterfalls” — it focused heavily on street violence and AIDS, two dominating topics of the ’90s.

CrazySexyCool almost instantly became a classic. Yet, there was strife. The late Lisa “Left Eye” Lopes was less involved on the album because of her stint in rehab for alcoholism. Her romantic relationship with Atlanta Falcons star receiver Andre Rison was constant tabloid fodder; the apex of their union was Lopes setting fire to his Atlanta mansion in June 1994. And at the height of the group’s popularity — on July 3, 1995 — TLC filed for bankruptcy. The group would settle the suit a year later, but as with Tyson, TLC’s money seemed to never have truly been theirs.

Styles P reminisces about The LOX reluctantly planning to jump Tyson for ‘talking crazy’ to Eve at The Source Awards.

Yet the most notorious event of the year took place two weeks before Tyson’s return. The ’95 Source Awards in New York forever changed the landscape of rap — and pop culture. The tense evening eerily paralleled the energy Tyson carried within and outside of the ring. OutKast’s Andre 3000’s proclamation that “the South got something to say” was not only true, it was fearless. The night is also forever tattooed in history for shining a light on simmering East Coast/West Coast hip-hop resentments: This was when Suge Knight infamously stated, “Come to Death Row [Records]” in a speech aimed at Sean “Puffy” Combs’ Bad Boy Records. Beef. Backlash. Bankruptcy. And the grimy romance of the streets. This was the vibe surrounding Tyson’s comeback.

Mike Tyson, in the late ’80s and into the ’90s, was a symbol of black male deviance. “[Tyson] was the sort of character that was used to justify the 1994 Crime Bill — an important moment in African-American history, but really U.S. history,” says Dr. Damion Thomas, the National Museum of African American History and Culture’s curator of sports. “What’s important in the mid-’90s is a [1994] book called The Bell Curve … it says that African-Americans are doomed to intellectual inferiority. … It’s also tied into this moment where people are starting to look for ‘the crime gene.’ Tyson becomes emblematic of this particular moment as well.”

And for almost any black person who came of age in the ’90s? A jovial question was very often, “You gettin’ the Tyson fight this weekend?” Though most ended quicker than the time it took to pour a drink, Tyson fights were community gatherings. This was before social media, and before streaming. Being present mattered. There was a sense of urgency when watching Tyson. And with that sense of urgency came a cloak of invincibility for viewers that Tyson himself wore like mink.

Urban legends revolved around Mike. He purchased BMWs for women he met in clubs — only to have his handlers retrieve them later. Tyson scared the late Charlie Murphy with a pet lion. When Tyson dented his Bentley, he gave the car to the attending police officers (who were eventually suspended). Tyson allegedly accused Michael Jordan of sleeping with his then-wife Robin Givens, who later accused him of spousal abuse and then, with no prenup in place, left him and relinquished all claims to Tyson’s then-$40 million fortune. And the skepticism of Tyson’s character boiled over with the ’92 rape case.

Tyson’s rape case lasted 15 days, culminating in a unanimous guilty verdict. He served three years for rape. “I didn’t rape that girl,” he said. “I did put myself in that position [of leaving myself susceptible to the charge]. I take responsibility for that.” Tyson could have been released from prison a year earlier under the condition that he admit to the crime. He refused.

KRS-One’s “Say Gal” attempted to lyrically vindicate the boxer, attaching more blame on the boxer’s victim. Blackstreet’s “Booti Call,” co-produced by Erick Sermon, was far less accusatory but nonetheless a kite to the incarcerated Tyson. Tupac Shakur immortalized the former champion on 1995’s “It Ain’t Easy” from his Me Against The World.

Gettin’ calls from my n— Mike Tyson, ain’t nothin’ nice Yo ’Pac, do somethin’ righteous with your life And even though you innocent you still a n— So they figure rather have you behind bars than triggers …

“The only difference in me and Mike is he’s big and I’m small,” Shakur said. “But I got the same heart he got. I wanna knock everybody out!” As Tyson exited prison in March 1995, Shakur was beginning his sentence stemming from a similar crime of sexual abuse. Shakur, too, ardently denied the crime of which he was convicted. And Shakur was leaving a Tyson fight (a win vs. Bruce Seldon) when he was gunned down in Las Vegas.

Tyson’s spirit was even a fixture on one of the decade’s most beloved sitcoms: Martin Lawrence donned a “Free Mike Tyson” T-shirt in Martin’s September 1993 episode “Beat It.” And a glimpse of Tyson’s 90-acre Southington, Ohio, compound after his release from prison featured balloons and flowers from the likes of Spike Lee, Whitney Houston and Shaquille O’Neal. “He made a mistake and he paid for it,” O’Neal said then. “He’s my friend and I want to see him given a fair chance again to make it back to the top.”

Nearly 2,000 people in Harlem welcomed Tyson back with a “Day of Redemption” in June 1995. The Rev. Al Sharpton served as unofficial MC of the day, stressing the importance of the release of Tyson and other black men coming home from prison. That black males have long been targets of an imbalanced criminal justice system was the day’s overall theme. Maya Angelou sent a statement expressing her regrets for being unable to attend.

Tyson’s Aug. 19 return against journeyman Peter McNeeley, the same day the Mark Fuhrman tapes flipped the Simpson trial on its head, was central to many discussions around sports and morality. Calls to boycott Tyson rang nearly as loud as the support for him. His sincerity was questioned — as were his personal growth and maturity. Tyson was free physically, but in 1995 he was still tethered to the court of societal opinion. Tyson was reaping the reward for violence in sports, went one argument. Undeniable was the fact that Tyson was the quintessential American redemption story. But what did this redemption say about a society so willing to excuse and expunge the past, is what another asked in the weeks leading up to the culmination of Tyson’s comeback.

And what a strange comeback it was. “You have to understand, he’s fighting somebody even I can beat,” promoter Bob Arum said before the fight. “[McNeeley] can’t beat anybody. He’s the stiff of stiffs. This is the equivalent of Tyson going into the gym and hitting the heavy bag or doing situps. It’s not even the equivalent of watching him spar.”

Though most ended quicker than the time it took to pour a drink, Tyson fights were community gatherings.

But a throng of celebrities was front and center: Michael Jackson, Eddie Murphy, Shaquille O’Neal, Jerry Seinfeld, Jim Carrey, Denzel Washington, Patrick Ewing, George Clooney, among a sea of others. Over 16,000 piled into the MGM and saw Tyson knock McNeeley down twice — that part they paid for. McNeeley’s manager Vinny Vecchione pounced in the ring, immediately disqualifying McNeeley — that part they didn’t. Boos and jeers pelted the decision. Tyson spent 50 months in prison, then trained for five months to step back into the ring — and it was over in 89 seconds. The fight was labeled a disgrace to the sport, although McNeeley and Tyson would maintain a warm friendship for years.

Twenty-three years ago, no one knew then he’d eventually recapture his heavyweight title. No one knew a Mike Tyson fight would be the last public event attended by Tupac Shakur. And no one knew just how much further he’d hit rock bottom — from the publicly embarrassing ear-biting incident to declaring bankruptcy, as well as the tragic and sudden death of his 4-year-old daughter Exodus — before becoming the sports Yoda he’s been in current times.

All anyone knew for sure on Aug. 19, 1995, including Tyson himself, was Mike Tyson was back. Don’t go chasing waterfalls / Please stick to the rivers and the lakes that you’re used to / I know that you’re gonna have it your way or nothing at all / But I think you’re moving too fast. As if the block needed to get any hotter.