A graffiti artist hailed as genius, Basquiat began dating the then-unknown Madonna around 1983, according to unofficial Madonna biographer Andrew Morton. Hanging out with Basquiat and his friends Andy Warhol and Keith Haring, Madonna was caught up in one of the most creative periods in the New York City's cultural history, and it's no surprise, said Morton, that she has since become a serious collector of modern art. Basquiat died from an overdose in 1988.
John "Jellybean" Benitez
A deejay and musician, Benitez met Madonna around the same time she met Basquiat, when her bandmate in the group Breakfast Club introduced them. This lead to both a working and a romantic relationship. "She didn't bowl me over at first," Benitez said in "Madonna: The Book." "We just used to go to the movies and clubs together. Then we started holding hands and buying each other presents."
Benitez produced and remixed most of the tracks on Madonna's self-titled debut album in 1983. After the release of her first album, Madonna, according to "The Book," was ready to move on -- professionally and personally.
When the Oscar-winning actor married Madonna in 1985, the couple instantly attracted the media glare. According to The Times of London, the media helicopters were so loud at their wedding, they couldn't hear their own vows. The press became the bane of their relationship and led to several violent outbursts from Penn, including an assault against a photographer for which he spent 32 days in jail.
Penn blamed his pride and alcohol for their marriage failing. He told contactmusic.com: "I describe that marriage as loud. ... I don't recall having a single conversation in four years of marriage. I've talked to her a couple of times since, and there's a whole person there. I just didn't know it."
John F. Kennedy Jr.
In "American Legacy," Rob Littell, a close college buddy of John F. Kennedy Jr., tells author C. David Heymann that during the summer of 1988 Madonna and Kennedy, who had secretly dated, had finally planned to go all the way in a "cheap, dinky Chicago motel."
"They were working their way around the bases, and as they rounded third and headed for home, she asked him if he had any protection. He didn't, so now they began discussing how they were going to get hold of a prophylactic," Littell told Heymann.
Because Madonna was still legally married to Penn and Kennedy had a close girlfriend, they were too afraid of being busted to visit the nearest pharmacy. "To John's great chagrin," Littell said, "the relationship was never completed."
Madonna became friends with the comedian in the late 1980s, and their closeness sparked rumors of romance. When the pair appeared on "The David Letterman Show," they intimated a romantic relationship, and Sandra joked that she had slept with both Madonna and her then husband, Sean Penn.
Years later, on contactmusic.com, Bernhard admitted that the relationship was just platonic, but that she enjoyed the press speculation.
"It was awesome at the time," she said. "We had a really funny friendship and kind of played with the press and the media. It was before the Internet and there was still a little bit of allure and excitement and fun to it."
The friends have since had a falling out and reportedly no longer speak, according to the New York Post.