Who's Madonna With Now?

Madonna and her romances have the media buzzing and people talking.

ByABC News
July 7, 2008, 7:03 PM

July 8, 2008— -- Though Cynthia Rodriguez's divorce papers make no mention of Madonna, her attorney Earle Lilly told ABC News affiliate KTRK the "final straw" that broke her six-year marriage to Yankees slugger Alex Rodriguez was his alleged affair with the pop superstar.

In this week's cover story titled "It's Over," Us Weekly magazine reports that Alex paid late-night visits to Madonna's New York apartment, something they both denied, and that the pop superstar's marriage to film director Guy Ritchie is essentially over.

Madonna fired back Sunday with a statement to People magazine in which she denied any romantic involvement with Alex Rodriguez and said that her marriage was not on the rocks.

"My husband and I are not planning on getting a divorce," she said. "I brought my kids to a Yankee game. I am not romantically involved in any way with Alex Rodriguez. I have nothing to do with the state of his marriage."

When it comes to affairs of the heart, it seems, whoever the Material Girl is linked to makes headlines, regardless of whether it's a confirmed romance or mere rumor. Since she first burst on the scene in the early 1980s, Madonna has reportedly coupled with a laundry list of artists, actors and athletes, men and women, A-listers and unknowns (that is, until she started dating them).

Ian Drew, editor at large at Us Weekly, says Madonna has found a way to mingle her many relationships with her career ascent and her family goals.

"She was with Carlos Leon at the time she wanted to have a baby," he told ABCNEWS.com. "She was with Warren Beatty when she had a movie to promote. She was with Michael Jackson as a date one night when she wanted to make a big splash at the Oscars."

She's a very creative person," Drew said. "She's always been up for trying different things. She loves experimenting with different types of people and not having boundaries."

That would explain the women she's been linked to as well as rumored couplings with artists as disparate as Jean-Michel Basquiat and Vanilla Ice.

Psychologist and relationship expert Bethany Marshall, an author and family and marriage therapist, believes Madonna takes on a new persona with each relationship. With British filmmaker Ritchie, it was lady of the manor, complete with an affected English accent.

"Madonna is really good at reinventing herself," she said. "Perhaps what's adaptive in professional life and makes hers so popular in her professional life is maladaptive in her personal life. She reinvents rather than reapplies herself to the commitment."

She noted that it also can't be easy being with someone as high profile as Madonna.

"You probably have to find someone who has the same level of fame and achievement to stand up to you," Marshall said.

"It's definitely hard to travel in her wake," Drew said. "She's going to control everything in her life. She overshadows things. He becomes Mr. Madonna."

So what might the attraction be between Madonna and Alex, if any? "Alex falls into her type," said Drew, "big athletes who sort of boss her around, masculine figures."

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.

Sean Penn

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."

Sandra Bernhard

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.

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.

Lenny Kravitz

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."

Vanilla Ice

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."

Dennis Rodman

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."

Carlos Leon

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.

Madonna met her current husband in 1998 at Sting and Trudie Styler's country home in England. According to Us magazine, she was attracted to his strong personality. "He was the only guy to ever really stand up to her," a source told Us.

The couple had a son, Rocco, two years later and got married two years after that at Scotland's Skibo Castle. Before they married, Ritchie told the audience at the MTV Europe Awards, "I would like to 'big it up' for the missus for winning so many awards and keeping Rocco in diapers."

And, reportedly, he didn't bother with a prenuptial agreement. USA Today quoted him as saying, "I don't want a penny if this marriage dies."

According to Us, the marriage is dead. "It's over for her and Guy," Drew said. "Sources say they're in the last stages of relationship. They're trying to do it amicably after her 50th birthday and after the tour. They weren't ready for this to come out yet."