12 Celebrity Scandals That Completely Rocked The 1990s

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The following article contains mentions of sexual abuse, domestic violence, and addiction.

For as long as there have been celebrities in the spotlight, there have been headline-making controversies. Even old Hollywood has had its scandals, from crimes to affairs and contentious feuds. But if there was ever a decade to take the cake for the wildest celebrity scandals, it's the 1990s. It was the time of MTV, the Spice Girls, the grunge aesthetic, and a major shift in pop culture.

There was no internet to keep track of all the Hollywood couple splits, celebrity arrests, or other unbelievable scandals. Instead, everyone tuned into entertainment shows or had their noses in gossip magazines to find out the latest Hollywood misdeeds. Whether it was Julia Roberts' untimely split from Kiefer Sutherland, the heated murder trial of O.J. Simpson, or the president's sordid affair, there were a number of celebrity scandals that completely rocked the '90s, subsequently making the stars' improprieties of previous decades pale in comparison.

Julia Roberts and Kiefer Sutherland's short-lived romance was a major talking point of the '90s, and it all started back in 1989 when the two met while filming "Flatliners." Sutherland filed for divorce from Camelia Kath in February of 1990, while the "Steel Magnolias" star ended her engagement to Dylan McDermott that same year. In August of 1990, Roberts and Sutherland then announced that they were planning on getting married. However, just a few days before Roberts was due to tie the knot with her beau on June 14, 1991, she called off the wedding. In fact, the "Pretty Woman" actor was spotted with Sutherland's good friend, actor Jason Patric, flying to Ireland that same day.

While there were undoubtedly hard feelings at the time, it seems that the former couple have since buried the hatchet. "I think she had the courage," Sutherland said while on "The Jess Cagle Interview" in September 2016. "It wasn't what she wanted to do in the end. And it think it took a lot of courage, in amongst all of that other stuff, to be able to say, 'I can't do this.'" And although Roberts was once a source of tension between Sutherland and Patric, the actors have fortunately managed to rekindle their friendship, too.

If Paul Reubens doesn't ring a bell, perhaps his on-screen character Pee-wee Herman will. His alter ego was far more iconic than the actor himself, as Reubens starred as the loveable character in movies like "Pee-wee's Big Adventure" and the kids' series "Pee-wee's Playhouse" from the mid-'80s to early '90s. Sadly, his popularity was short-lived, as an arrest led to the downfall of his squeaky-clean image.

In 1991, Reubens was arrested for indecent exposure at an adult theater in Sarasota, Florida and his mugshot, in which he was long-haired and unrecognizable, was circulated. The arrest became a "major footnote" in his life, as the actor explained in the HBO documentary "Pee-wee as Himself" shortly before his death (via People). "It really backfired when I got arrested, and people had never seen a photo of me other than [as] Pee-wee Herman, and then all of a sudden I had a Charlie Manson mug shot," he remarked. "It's shocking what hideous, horrible, mean stuff people say and think about me."

Not long after, a raid was conducted on Reubens' home. The police seized his extensive collection of antique art and, in 2002, he was charged with the possession of child pornography. Although Reubens claimed to have no knowledge of anything improper, his reputation as a beloved children's television icon was ultimately ruined.

There's no denying that writer and director Woody Allen was an inspirational filmmaker back in the '80s and '90s. However, his reputation has since been his undoing, from his adoptive daughter Dylan Farrow accusing him of sexually abusing her in 1992 — when she was just 7 years old — to his romantic involvement with his own stepdaughter. Allen and Soon-Yi Previn's relationship timeline is highly contested, but it is known that sometime during the director's 12-year relationship with actor Mia Farrow, he began having an affair with Previn, her adopted daughter.

While the "Rosemary's Baby" star insisted the affair began while Previn was in high school, Allen stated they hadn't begun dating until she was in college in 1991. "I was madly in love with him," Previn revealed to Vulture in September 2018. "Completely attracted to him, physically and sexually ... I came to realize how understanding he was and what a sweet person he was. He grew on me." Ultimately, Previn stood by Allen's side throughout the allegations against him, of which the "Annie Hall" writer has vehemently denied, and the two tied the knot in 1997.

Irish singer, songwriter, and activist Sinead O'Connor was at the top of her game come 1990, when she released her second studio album, which featured her ultra-popular cover of Prince's "Nothing Compares 2 U." The track, which had reached number one on the charts, was everywhere — so, it was no surprise when she was asked to be the musical guest on an October 1992 episode of "Saturday Night Live."

O'Connor became the subject of controversy, though, when she used her live television performance to take a stand against child sexual abuse within the Catholic Church. After performing an a cappella version of Bob Marley's song "War," she tore up a picture of Pope John Paul II. O'Connor threw the pieces at the camera and instructed viewers to "fight the real enemy," which was met with shock and, eventually, a lifetime ban from NBC (via People). Despite the singer being absolutely right about the church's attempts to cover up child sexual abuse, her speaking out wasn't fully appreciated for years to come. "[I was] well aware there would be [backlash]," O'Connor told People in 2021. "I understood it."

Just a couple of years after she formed TLC with Tionne "T-Boz" Watkins and Rozonda "Chilli" Thomas, and less than a decade before her tragic, untimely death,  Lisa "Left Eye" Lopes found herself in hot water. The four-time Grammy-winning singer and songwriter had a tumultuous relationship with Andre Rison, wide receiver of the Atlanta Falcons, which culminated in a terrible fight-gone-wrong.

One night in June 1994, after the couple had been out partying separately, they returned to Rison's mansion. It was there that Lopes reportedly became angry that her boyfriend had purchased several pairs of sneakers for himself but none for her. "I knew she'd been drinking some," Rison told People in a later interview (via Paper), and he admitted to trying to calm her down by slapping her. "I didn't know what was upsetting her. I started taking blows to the face," he said. Eventually, Rison left his home and Lopes lit his sneakers on fire in the bathtub, but the flames quickly spread. The entire mansion became engulfed and ultimately burned to the ground. Lopes turned herself in the following day and was charged with felony arson.

Seeing Anna Nicole Smith's name on this list is far from shocking. The model, actor, and reality star has had a number of controversial moments over the years — but few things shocked the public as much as her June 1994 marriage to an oil tycoon who was old enough to be her grandfather. At just 26 years old, Smith tied the knot with 89-year-old J. Howard Marshall II, whom she met at a strip club she worked at.

Understandably, questions were raised over the legitimacy of the former Playboy Playmate's feelings for him, given their 60-plus-year age gap and Marshall's impressive net worth. "I know people think I married Howard for his money," she later said (via People). "But it's not true. I love him." Several months later, Smith was banned from seeing her husband, who was in poor health, up until his death in August 1995. Apparently, Marshall hadn't included the model in his will, so Smith spent the next few years embroiled in a court battle against his eldest son — who was ultimately found to be the sole heir of the oil tycoon's fortune.

Out of all the celebrity scandals that rocked the 1990s, O.J. Simpson's murder trial might be the most notorious. Unless you were alive before the media blitz, you might not realize how beloved the former football player-turned-actor really was. However, his tumultuous marriage to Nicole Brown Simpson was marred by domestic abuse and cops were frequently called to their address. One night in June 1994, years after the pair divorced, Nicole was found stabbed to death at her home, alongside Ron Goldman, a waiter from the restaurant she had eaten at earlier that night.

O.J. was interviewed by police the following day but wasn't arrested — that is, until the football star was ordered by prosecutors to surrender. Instead, O.J. and his friend Al Cowlings climbed into a white Ford Bronco and led the police on a slow-speed chase on the 405 freeway for an hour and a half. Eventually, the two surrendered, and O.J. was arrested and tried for both Nicole and Goldman's murders. As we all know, he was ultimately acquitted. Attorney Johnnie Cochran, who defended O.J., stood by him even after the trial. "Every lawyer who represented Simpson will tell you he always said, 'I'm innocent. I didn't do this, guys. This is my life,'" Cochran told SFGATE in November 1996. "He never wavered from that, and I believed him."

In terms of scandals that probably wouldn't have been as big a deal if they'd happened today, the public scrutiny Hugh Grant faced for his 1995 arrest is remarkable. He had been everyone's favorite charming, blue-eyed London native throughout the decade, portraying a number of dashing characters on screen. That is, until Grant was arrested in Hollywood for "lewd conduct" with sex worker Divine Brown (born Estella Marie Thompson) in his car. Although he faced six months in jail, what was more damning was his public image that had been torn to shreds.

At the time, Grant had been dating actor Liz Hurley, so when news broke of his arrest, he was also labeled a cheater. "Last night I did something completely insane," Grant said in a statement released by The Guardian at the time. "I have hurt people I love and embarrassed people I work with. For both things, I am more sorry than I can ever possibly say." Fortunately for the "Four Weddings and a Funeral" star, the public seemed to quickly forgive him for his ungentlemanly behavior.

While you might just remember the shocking moment Mike Tyson performed the infamous and illegal move in the ring against Evander Holyfield back in June 1997, there was a long string of events that led up to it. After becoming the youngest heavyweight champion in 1986, the boxer displayed erratic behavior that contributed to his downfall, including fights, lawsuits, car accidents, and a rape conviction.

Tyson was desperate to reclaim some portion of his glory when he was released from prison, and a match between himself and the retired Holyfield was set for November 1996 — but this wasn't the infamous match. After beating the former champ, Holyfield agreed to a rematch in which Tyson lost his composure quickly. During the third round, he spat out his mouthpiece and bit off a piece of his opponent's ear. After a brief timeout, the match resumed and Tyson bit Holyfield's other ear in a shocking display of poor sportsmanship.

In Jim Gray's 2020 book "Talking to GOATs," the sportscaster revisited the controversial moment with the boxing legend. When asked whether he would ever bite someone's ear like he did Holyfield's again, Tyson's answer surprisingly wasn't a straight "no." Instead, he replied, "I hope not. I say, 'No, never ever again.' But I might do it again. Well, if he does what he was doing to get bitten, I would bite him again. Yeah."

While a major political figure having an affair might not be as shocking today as it once was, Bill Clinton's affair totally rocked the '90s when it was brought to light. It's also a scandal that would probably be looked at from a different lens today, seeing as how Monica Lewinsky was a 21-year-old unpaid intern at the White House when she and the president entered into a sexual relationship back in November 1995. The following month, she was promoted into a paid position.

Lewinsky confided in her friend and co-worker Linda Tripp about the affair, and their conversations were secretly recorded by Tripp. A former government employee, Paula Jones, was in the midst of a legal battle after accusing Clinton of sexual harassment and, upon hearing Lewinsky's story, the existence of the tapes loomed. Before long, everyone knew of the president's affair, leading to his infamous statement: "I did not have sexual relations with that woman." After Lewinsky's equally infamous blue dress, which contained the former president's DNA, became evidence, Clinton admitted to his infidelity. He was ultimately impeached in December 1998.

In May 2014, Lewinskey wrote for the first time about the scandal in Vanity Fair. "It's time to burn the beret and bury the blue dress," she penned. "I, myself, deeply regret what happened between me and President Clinton. Let me say it again: I. Myself. Deeply. Regret. What. Happened."

The Robert Downey Jr. of Marvel fame is far from the actor everyone came to know back in the '80s and '90s. After working his way up in Hollywood with roles in "Weird Science," "Tuff Turf," and "Saturday Night Live," Downey Jr. had a very public fall from grace. It seemed Downey Jr. was set to become one of the greats, alongside the rest of the Brat Pack, but his issues with addiction soon took over. Downey Jr. found that playing a drug addict in 1987's "Less Than Zero" fueled many of his issues, and he struggled to get through other projects during this time. However, he did manage to snag an Oscar nomination for his work in 1992's "Chaplin."

In 1996, Downey Jr. was found in possession of heroin, cocaine, and a gun. The following month, he trespassed and fell asleep in a bedroom belonging to a neighbor's child. Eventually, after breaching probation several times, Downey Jr. stood before a judge in 1999. "It's like I have a shotgun in my mouth and I've got my finger on the trigger, and I like the taste of the gunmetal," the actor begged the judge (via Vanity Fair). Downey Jr. was sentenced to three years, but it still took him some time before he quit drugs altogether. While many '90s stars have tragically died, Downey Jr. was fortunate enough to make it through and turn his life around before it was too late.

We all know that Sean "Diddy" Combs got up to no good during the height of his fame, but hindsight is 20/20. Back in the day, long before the public knew the extent of the rapper's misdeeds, P. Diddy was in a relationship with Jennifer Lopez. The musical duo began dating in 1999, and while they called it quits just two years later, it wasn't due to the controversial moment they had at the end of the '90s.

While at a Manhattan club one night in December 1999, Diddy, Lopez, and a couple other patrons had a disagreement that cascaded into gunshots ringing out. Three people were shot and the Hollywood couple fled the scene, leading police on a chase. Both Diddy and Lopez were arrested, though the charges against the "Let's Get Loud" singer were dropped. The shooting was a "complete nightmare," she later told British Elle (via Forbes). "I was scared to death in the car. I had absolutely no idea what was going on."

If you or anyone you know has been a victim of sexual assault, needs help with addiction issues, or is dealing with domestic abuse, help is available:

• Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).
• Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).
• Call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.