Who: Grammy-winning singer and Golden Globe-winning actress Madonna, 61, and Grammy-nominated rapper Robert Van Winkle (aka Vanilla Ice), 52.

How They Met: Accordi. Ice himself, Madonna "came after" him at one of his shows in N.Y.C. in the early '90s. "She's aggressive. She wanted me," he said on an episode of the Dan Patrick Show. "She was much older, ,so I was like 'Whoa, what's going on with this?' She came into the dressing room right after the show. S,he grabbed me and we were having cocktails that night." (Note: Ice's mention of his and Madonna's slight age difference is a press tour favorite of his.)

Why We Loved Them: What could better encapsulate the culture and surreality of the early '90s than two wildly confident stage name-bearing performers teaming up (in the name of love!). Scratch that last part — Ice is adamant that they were not in love.

When They Peaked: When grilled about this relationship with Madonna on George Stroumboulopoulos Tonight more than two decades after their split, Ice told the talk show host his ex "was a sweetheart," explaining, "You take away the fame and everything and you got two people who just basically had a normal relationship." While their time together was very normal, Ice added that they'd go to the movies in disguise. "I had a mustache and hat with hair coming down, and she would go as an old lady."

The Breakup: 92, all that anyone could talk about was Sex — Madonna's erotic coffee table book (that I once found in my grandparents' apartment and am forever scarred by). Though it was a commercial success, critics deemed the book contrived. The work, meant to titillate and shock viewers, was comprised of photos of her Madgesty (Madonna's nickname) engaging in envelope-pushing sexual acts with myriad partners. The few heterosexual photos in the book featured Madonna and Vanilla Ice together — the latter of whom was reportedly thrown in "for his kitsch value." Sex was a spectacle, but not the fun Madonna-wears-cone-bra-on-stage kind.

Ice, who's said quite a bit about their breakup through the years, told News of the World he blamed the split (which he said he initiated) on the infamous book. While he said dating Madonna was partlyng" — in part because "she was older than me and a great lover. She's still the oldest person I've ever been with, so it was an experience" — he "broke up with her after she printed that book because I was hurt to be an unwitting part of this slutty package." He continued, "It was disgusting and cheap. We were in a, relationship yet it looked like she was screwing all these other people. I thought she was taking pictures and running 'round naked because she was like that. Then when the book came out I was so embarrassed and ashamed. It was a porno. She threw me in like I was a product off a shelf and I didn't appreciate it. That was it and I ended it. She said she didn't have sex with these men but it looked like she was." Madonna never responded to these specific claims about his knowledge of the book.

In 1994, Ice told USA Today that during their year-long, relationship Madonna would call him "at strange hours" demanding to know whether he was with someone else. He also said, "She's very sexy, she's hot, she's romantic. She's got a great body for her age." Yes, you read that correctly: FOR. HER. AGE.

Ahead of the release of Andrew Morton's Madonna biography in 2001, People ran an article with quotes from Ice, explaining that while he "was digging her," there was also "a desperate neediness about her, an impatience to get married." so said that Madonna was still in love with her ex-husband Sean Penn. "I felt that she still loved him," he said. "In fact, I know she did because she told me." In a review of Morton's book in The Guardian, another shady Ice quote was pulled: "If [Madonna] were a painting, she would be an abstract by Picasso. She has so many faces."

Don't worry; Madonna also got a chance to speak her piece. In an interview with Us Weekly in 2015, the singer said if she had to choose either Ice or ex-boyfriend Dennis Rodman to be stuck on a desert island with, she'd choose Rodman because "He has a better sense of humor. Plus, he could always wear my clothes."

TBT: Julia Roberts Had One Regret About Her Breakup from Benjamin Bratt

Where They Are Now: Madonna went on to wed director Guy Ritchie in 2000. They finalized their divorce in 2008. Madonna is a mother of six: Lourdes Leon, Rocco Ritchie, Mercy James, David Banda Mwale Ciccone Ritchie, Stelle Ciccone, and Estere Ciccone. In 2019, Madonna released her 14th studio album, Madame X.

Vanilla Ice married Laura Giaritta in 1997. They share two children: Dusti and KeeLee. The longtime couple finalized their divorce in 2019. Also, in 2019, Ice starred in his own show about his contracting business, The Vanilla Ice Project.