1995: Prince Charles vs. Princess Diana
The People’s Princess and her husband, Prince Charles, had separated way back in 1992, and the dissolution of the royal couple’s marriage was a source of endless fascination. In 1994, Charles admitted to cheating on her with Camila Parker Bowles, and the following year, Princess Di finally sat down for her first solo interview. “There were three of us in this marriage, so it was a bit crowded,” she revealed, while also admitting she’d been unfaithful. It got so much attention that a month later, the Queen wrote the pair a letter telling them to hurry up and divorce already.
1996: Tupac vs. The Notorious B.I.G.
After Tupac was shot in Manhattan, Biggie released the track “Who Shot Ya?”, which the former interpreted as a diss track. He responded in turn with multiple disses of his own, heating up a coastal rap war. Of course, this epic feud came to an end in September of ’96, when Tupac was shot and killed in a drive-by. Six months after that, Biggie suffered the same fate. Both deaths remain officially unsolved.
1997: Evander Holyfield vs. Mike Tyson
You gotta do what it takes to win, and if you’re Mike Tyson, that means sinking your teeth into some human flesh. In the third round of the now-notorious “Bite Fight” between the two boxers, Tyson bit off a chunk of cartilage from Holyfield’s ear. Tyson was disqualified, giving Holyfield the win — if you call coming out of a fight with less than two full ears winning. Tyson was fined $3 million and had his boxing license revoked.
1998: Monica Lewinsky vs. Bill Clinton
Stop us if you’ve heard this one before: woman gets the internship; a woman has multiple sexual encounters with a president of the United States; president declares he “did … not … have … sexual … relations … with that woman”; woman’s blue dress disagrees.
1999: LL Cool J vs. Jamie Foxx
The two stars came to blows while filming their football movie Any Given Sunday. They played mere rivals in the movie but during shooting, things got so tense that both men punched each other in the face. Police were called but no charges were filed. It wasn’t just a friendly misunderstanding either — the following year, LL released the track “U Can’t Fuck With Me,” which included the line “Once and for all, what’s my opinion on Jamie Foxx? He’s a pussy.”
2000: Christina Aguilera vs. Eminem
Eminem got real shady when he dropped this jaw-dropping line in “The Real Slim Shady”: “Christina Aguilera better switch me chairs, so I can sit next to Carson Daly and Fred Durst, and hear ‘em argue over who she gave head to first.” Aguilera did not take kindly to the accusation, telling MTV News, “It’s disgusting and offensive and above all, it’s not true.” Two years later, Aguilera released the feminist anthem “Can’t Hold Us Down,” which presumably references Eminem when the pop star sings, “It’s sad you only get your fame through controversy.”