Although she is one of the most famous and successful women in the world, Madonna has not always have been lucky in love. She has, however, never been shy about opening her heart.
Step back in time with Access Hollywood as we look back at the celebrity men Madonna has romanced over the years.
Madonna and Sean Penn began dating in 1985 and were married that same year. Photos of and stories on the couple were as hot then as ones of Brad and Angelina are now.
The fiery relationship between Madonna and Sean was immediate tabloid fodder as the couple was eagerly hunted by the paparazzi. During their relationship, Sean got a reputation for lashing out at anyone attempting to photograph the couple.
He was arrested in 1987, after assaulting an extra on the set of “Colors” for trying to take his photo without permission.
In an interview with Rolling Stone in 1987, Madonna defended the couple’s fiery romance.
“All this talk… is heightened dramatics,” Madonna said. “We are a ‘Hollywood couple,’ so people are going to pay a lot of attention to our marriage and whether it’s going to work or not… If we have our fights, I think that’s pretty normal for young people in their first few years of marriage. It’s normal for anybody who’s married, but when you put all the pressures that we’ve had on top of that, I think the fact that we’re still together is pretty amazing. You know, we’re working it out, and that’s all I can say…It’s easy to give up, but it’s not easy for me to give up.”
The couple eventually divorced in 1989.
Though he was 21 years her senior, nothing could stop the romance between Madonna and Warren Beatty in 1990 after the two starred together in “Dick Tracy.” The two hit the premiere of the film arm in arm and though their romance fizzled, their on-screen match up resulted in the film grossing over $100 million at the U.S. box office.
Just as rap began to rule the pop charts, Madonna took up with one Robert Van Winkle, AKA Vanilla Ice.
Their courtship began in 1991 and lasted eight months.
Before the two called it quits in 1992, the Ice Man ended up in some scantily clad photographs in Madonna’s infamous “Sex” book.
Speaking to USA Today in 1994, Van Winkle recalled the ups and downs of their relationship.
“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?’” he recounted. “But is she a sexual animal? Nah, she’s like every normal girl, man. She’s very sexy, she’s hot, she’s romantic. She’s got a great body for her age .”
The Queen of Pop began a romance with the then king of the basketball court, Dennis Rodman, in 1994. Madonna was seen behind the scenes at his basketball games and Dennis even turned up at the MTV Movie Awards.
“I love Dennis Rodman,” Madonna once told USA Today. “He’s hot. I adore him. He’s a rebel, the Madonna of the NBA.”
Rodman has since claimed Madonna not only wanted his child, but also wanted to marry the former NBA star.
The same year she ended her fling with Rodman, Madonna met Carlos Leon, a personal trainer, who would become one of the most significant men in her life two years later after he fathered her first child, daughter Lourdes.
Leon became Madonna’s personal trainer after their meeting and for over a decade, he has remained a constant in the “Material Girl’s” life.
In October 2008, Leon confirmed to Access Hollywood’s Billy Bush for “The Billy Bush Show,” that the two are still close.
“Any parent that stays friends, it’s really good, it’s good for the children, it’s good for family values, it’s good for a lot of reasons,” Leon said. “You gotta keep it mutual and try to keep it cool.”
In 1999, after being set up at a dinner party hosted by Sting and Trudie Styler, Madonna began dating “Lock Stock & Two Smoking Barrels” director Guy Ritchie. The two married in December 2000 at Skibo Castle in Scotland, where Stella McCartney served as Maid of Honor.
Like her relationship with Sean Penn over a decade earlier, Madonna’s romance with Guy was a paparazzi gold mine from the start. And like Penn, Ritchie was also arrested after assaulting a fan. According to the British media, Ritchie was arrested in 2000, after hitting a man who was stationed outside the London home he shared with his wife who was then pregnant with the couple’s son, Rocco.
Though early tabloid reports suggested the couple were having problems in 2000, they remained together, eventually adopting a child, David Banda from Malawi in 2006.
In August 2008, weeks after rumors of an affair with NY Yankee Alex Rodriguez emerged, Ritchie showed his support for his wife, turning up to the start of her “Sticky & Sweet” tour in the U.K..
“Her legs are Olympic standard. She is in amazing shape. You won’t find a fitter bird than her,” Ritchie raved to Britain’s The Sun newspaper. “Her legs are so toned. She’s fitter than dancers on her tour who are half her age.”
Related Content from AccessHollywood.com:
PLAY IT NOW: Madonna & Guy Call It Quits
PLAY IT NOW: AUDIO: Carlos Leon On Madonna’s Divorce (Oct. 15, 2008)