The former Hollywood lothario dated Madonna in the late '80s and early '90s when he directed her in the film "Dick Tracy." According to People magazine, the twosome were not shy about showing public displays of affection, necking on set and cuddling at Hollywood gatherings.
Beatty also made a famous appearance in her documentary "Truth or Dare" in which he criticized her for not doing anything off-camera. Still, cynics believed the odd coupling was nothing more than a publicity stunt.
"Warren and Madonna are still an item, but nobody believes it," her publicist Liz Rosenberg told People at the time. "She's not seeing anybody else. It's Warren and Warren only."
The romance didn't last, but Beatty's marriage to Annette Bening is still going strong after 16 years and four children.
In 1991, the rocker produced Madonna's video "Justify My Love," and the media speculated that they were involved in a relationship. It's never been confirmed, but Kravitz has resurfaced in this latest scandal. After Cynthia Rodriguez left Alex, she fled to Kravitz's home in Paris, leading to speculation that they were involved.
Kravitz released a statement to Us Weekly, saying, "There is absolutely no affair between Cynthia Rodriguez and myself. This is unequivocally 100 percent not true."
The rapper and Madonna were together for eight months in 1992. In 1994, he told USA Today: "She would call me at strange hours, 'Are you in bed with another girl?' At 6 in the morning, man, I'm like, 'I'm [expletive] sleeping all alone. What the [expletive]? Why do you keep doing this?'
"But is she a sexual animal?" Vanilla Ice said. "Nah, she's like every normal girl, man. She's very sexy, she's hot, she's romantic."
The outlaw NBA basketball player wrote in his autobiography, "I Should Be Dead by Now," that Madonna wanted to have his baby and was serious about getting pregnant during the couple's reportedly brief fling in 1995.
"One time I was in Las Vegas at the craps table doing my thing when I got this frantic call," Rodman wrote. "It was like the 'Somebody died call' from New York. I picked up the phone and Madonna was like, 'I'm ovulating, I'm ovulating. Get your ass up here.'
"So I left my chips on the table, flew five hours to New York and did my thing. We got done and she was standing on her head in an attempt to promote conception -- just like any girl trying to get pregnant. I flew back to Las Vegas and picked up my game where I left off."
Madonna told USA Today at the time she was dating Rodman: "I love Dennis Rodman. He's hot. I adore him. He's a rebel, the Madonna of the NBA."
When Madonna was reportedly shopping for someone to father a child, she happened upon personal trainer Leon, or rather he happened upon her. He approached her in 1994 while she was jogging in Central Park and not only became her trainer but the father of her child.
They had daughter Lourdes "Lola" Maria Ciccone Leon in 1996 but broke up less than a year later. Still, the relationship changed his life. Leon, who has since guest starred on several TV shows, told TV Guide that he got a tattoo that reads "September 8 Forever " to commemorte the day he met Madonna. "That's the day my whole life changed," he said.