The 7 Most Controversial Celebrities of the ’90s

1 | O.J. Simpson

You can't have a list of controversial '90s celebrities without mentioning O.J. Simpson. After the former NFL player was charged with the murders of his ex-wife, Nicole Brown Simpson, and her friend, Ron Goldman, in 1994, his arrest and trial became a media sensation, and everyone had an opinion as to whether Simpson was guilty or not. After nearly a year, the trial came to an end, and the jury found him not guilty. (At the 1997 conclusion of a civil case, sports star was found responsible for both victims' wrongful deaths and ordered to pay their families $33.5 million.) The details of the case itself, the ruling, and Simpson's actions afterwards have only lead to continued fascination in the so-called "Trial of the Century."

2 | Sinéad O'Connor

Sinéad O'Connor became famous worldwide thanks to her version of "Nothing Compares 2 U," but the Irish singer made headlines for a far different reason two years after the cover became a massive hit.

In 1992, O'Connor appeared as the musical guest on an episode of Saturday Night Live. She sang "War" by Bob Marley and used the performance to protest against the rampant sexual abuse of children in the Catholic Church. But, the part that went too far for many viewers was when O'Connor took out a photo of Pope John Paul IIand tore it up while saying, "Fight the real enemy."

"'Sinéad O’Connor’ was never meant to be a pop star,” she told Today in 2021. “I was really a protest singer, you know?” She added that she had no regrets about limiting her own career by speaking out. "It was a blessing because I had to make my living doing the thing I loved doing, which is making music live."

In the years since O'Connor's statement infuriated viewers, instances of child abuse and systemic coverups within the church have become much more well known.

3 | Eminem

In the late '90s, rapper Eminem came to fame with his first major single "My Name Is." But while the song was a big hit, especially on MTV, not everyone was a fan. Eminem was criticized for his lyrics, which include fantasizing about committing acts of violence against his ex-wife, homophobia, sexism, and other offensive topics. He also frequently bashed other artists and public figures in his songs, leading to some awkward TRL appearances. Per CNN, former Second Lady Lynne Cheney once referred to the artist, who was also critical of the Bush administration in his songs, as a "violent misogynist."

While Eminem has continued to court controversy, his career never again quite hit the heights of the '90s and early 2000s.

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4 | Britney Spears

Britney Spears, an alumnus of Disney Channel's The All-New Mickey Mouse Club, was only 16 when her first hit single "...Baby One More Time" was released and became an instant smash. While some of her many critics simply hated the teen's bubblegum pop music, others were bothered by her songs' suggestive lyrics and revealing clothing. This backlash was only furthered by her controversial 1999 Rolling Stone cover, which is only one example of her being sexualized in the media prior to being an adult. (As for the lyrics part: it turns out the "hit me, baby" part was actually supposed to mean "call me, baby".)

Of course, the former teen star would continue to make headlines for her relationships, her appearance, and her behavior in the years to come. But in more recent times, the manner in which the media treated her as a young star has been widely reevaluated.

5 | Hugh Grant

In the mid-'90s, Hugh Grant's leading-man career was taking off in a flurry of rom-coms and period films. But in 1995, the star was arrested in Los Angeles for hiring a sex worker named Divine Brown, a news story that eclipsed all of his success. As if the release of his mugshot didn't get enough tongues wagging, the actor was also in a public relationship with fellow actor Elizabeth Hurley at the time, so he was denounced as a cheater.

As The Guardian reports, Grant was order to pay a $1,000 fine and to take an AIDS education course. He publicly apologized to Hurley and shared his regret about the incident, including in a sheepish but well-received appearance on The Tonight Show. And then the star moved on with his career. Both it and his public reputation bounced back.

6-7 | Pamela Anderson and Tommy Lee

Pamela Anderson was one of the biggest bombshells of the '90s, famous for posing for Playboy and starring on Baywatch. Tommy Lee was famous for being the drummer of the hard-partying band Mötley Crüe and for his marriage to Heather Locklear. In 1995, the two stars met and were married only four days later. That alone was a shock, but not long after, their private sex tape was stolen and published online, leading to a huge amount of invasive attention. There were rumors at the time that the couple was somehow behind the release of the tape, but the lawsuits they filed said otherwise. The couple divorced in 1998; that same year, Lee was sentenced to six months in prison for spousal abuse. Now, in 2023, Anderson is speaking out about how all of this impacted her in a new memoir and documentary.