What Madonna's Exes Have Said About Her

Though she started out as a dancer, Madonna is as successful a musician as they come. She is the Queen of Pop, whose claim to fame is being one of the best-selling musicians of all time. Forbes estimates Madonna's gross concert ticket sales at $1.2 billion. According to Billboard, her albums have maintained a top spot on the charts, year in and year out.

Outside of work, Madonna's love life is just as active. Sex is the fuel that tickles her fancy, she shared on "Finally Enough Talk: 50 Questions with Madonna." Now in her mid-60s, the singer has gained notoriety for dating younger men. During an appearance on "The Ellen DeGeneres Show," Madonna revealed that she didn't really pay attention to the ages of her lovers.

"I've dated all sort, all kinds. I dated Warren Beatty, I mean... Why is everyone so obsessed? Age is a number," she remarked. However, the singer was close in age to late artist Jean-Michel Basquiat. She told David Blaine for an Interview mag feature, "I remember getting up in the middle of the night and he wouldn't be in bed lying next to me; he'd be standing, painting, at four in the morning, this close to the canvas, in a trance. I was blown away by that, that he worked when he felt moved."

Over the years, many of the pop star's love interests have shared their thoughts on the one and only Madonna. Young or not, here's what they had to say.

Before Carlos Leon began dating Madonna, he was living in a humble New York City apartment with his parents. On September 8, 1994, his life took a sudden turn when a routine bike ride at Central Park led him to meet Madonna, per Inside Edition. The pairing, unlikely but unsurprising, soon became the talk of Tinseltown. Leon's once low-profile life shot through the roof, and as with all things Madonna, was subject to scrutiny.

In 1996, 38-year-old Madonna gave birth to a daughter, Lourdes Maria Ciccone Leon, per the Los Angeles Times. Lourdes has since taken on a career in music, according to USA Today. The relationship between Madonna and Leon, however, came to a halt. "I'm forever grateful to [Madonna]," Leon told People. "I have no regrets. I wouldn't change anything. I got the best thing out of that relationship, and that's my daughter. My daughter is everything to me."

That things ended didn't mean Leon wouldn't have an opinion on his former lover's personal life. During Madonna's 2008 divorce from Guy Ritchie, he let his thoughts be known to Hello! (via Marie Claire). "It is a bad situation for both Guy and Madonna and I send them a lot of love and all the children involved. I think it is too early to say if the divorce will make things better or worse for the family," he said.

"Dead Man Walking" actor Sean Penn has been married twice; first to Madonna, and a second time to "House of Cards" actor Robin Wright. For two years post-divorce, Penn dated Charlize Theron, and while he did not directly mention Madonna or Wright by name, he let Esquire UK (via People) know that his relationship with Theron was mature, unlike his marriages, where he had little to work with.

"You say I've been married twice before, but I've been married under circumstances where I was less informed than I am today," Penn told the publication. There seems to be no bad blood between the pair, if Penn's appearance on "The Late Show with Stephen Colbert" is taken into account. Asked whom he'd choose between Madonna and Britney Spears, Penn said, "I love my first wife very much...you don't compare those things."

Penn's sentiments might be echoed by Madonna's second husband, filmmaker Guy Ritchie — who directed the music video for "What It Feels Like For a Girl," from her eighth studio album, "Music." Ritchie opened up to the Mail on Sunday's Event magazine in 2017 (via Yahoo! News). "A marriage breakdown is a death. That is all I can say. Now I just want to say positive things about her. I don't regret being married to her, I don't, you know, not in the slightest," Ritchie said. He added, "She's a wonderful mother and has been very good to the kids." Ritchie and Madonna, who split in 2008, share sons David and Rocco.

It's clear that Madonna's dating life sometimes has a pattern, and her year-long relationship with Brazilian model-turned-DJ Jesus Luz follows the script to a T. Luz's $500-per-gig payday changed the day he met the "4 Minute" singer at a W magazine shoot, per The New York Times.

He disappeared in every sense of the word and went as far as changing his telephone number. In place of the low-budget jobs he'd been accustomed to, Luz's career went on an upward spiral. In addition to getting a modeling contract with Ford Models, he was walking on high-end runways and commanding $15,000 for a disk jockey gig.

Madonna may have split with Luz because they didn't have much in common, per the Chicago Sun-Times (via Today), but years after the pair called it quits, he gave credit where it's due. In a conversation with Revista Quem (via Yahoo! News), Luz acknowledged that his relationship with Madonna impacted his way of parenting. "I am extremely grateful to her. She inspired me to be the human being that I am today, more open to the unknown and more understanding of differences. I try to pass all this on to my daughter," he expressed.

In the '90s, rumors of a Madonna-Tupac Shakur relationship swirled around for a hot minute, but neither star confirmed whether they were true. It wasn't until Madonna's 2015 appearance on "The Howard Stern Show" that she spilled the tea. Stern asked why Madonna was belligerent during a past appearance on "The David Letterman Show," and she said Shakur was partially to blame: "I was dating Tupac Shakur at the time and the thing is, he like got me all riled up about life in general. So when I went on this show I was feeling very gangster." Madonna's connection to the "Dear Mama" rapper was co-signed by Snoop Dogg, who also came on "The Howard Stern Show."

In letters addressed to Madonna by Shakur, presumably written when he was in prison (via TMZ), the latter addressed concerns over race. "For you to be seen with a black man wouldn't in any way jeopardize your career, if anything it would make you seem that much more open and exciting," he wrote. "But for me at least in my previous perception I felt due to my 'image' I would be letting down half of the people who made me what I thought I was."

The rapper also confessed to having been upset that Madonna made a comment about being on a mission to amend rappers, writing in part, "...I had never known you to be with any rappers besides myself."

When a material girl meets a certified bad boy, the joy is likely to be fleeting but unforgettable. That was the case when Madonna crossed paths with NBA rebel Dennis Rodman. Theirs was reportedly a case of fiery passion from the beginning. Rodman wrote in his book "I Should Be Dead by Now" that the "Papa Don't Preach" star wanted to have children with him and called him out to New York when she was ovulating.

In a 1995 conversation with ESPN, Rodman confirmed his short-lived romance with the culture icon. "We had a fling," he said, adding that there wasn't much change in her persona within the two months they saw each other or afterward.

In Rodman's appearance on "The Breakfast Club" radio show, he said his image brought Madonna more notoriety, and not the other way around. "In 1993 I think her career was declining... she said that, you know, the reason why she dated me is 'cause I was a bad boy. That's why she dated me. So I was going up and she was pretty much leveling off," Rodman commented.

Madonna and Vanilla Ice had a good thing going in the early '90s. The pair's first encounter happened during an Ice concert in New York City, the rapper revealed during an appearance on "The Dan Patrick Show." Madonna found her way backstage when Ice was done performing, and wouldn't take no for an answer.

Speaking with George Stroumboulopoulos, Ice went in on more intimate details of their year-long relationship. "She was a sweetheart. We had great times. I mean, you know, you take away the fame and everything and you've got two people who just basically had a normal relationship," he said. The pair would use moustaches and hats to camouflage whenever they went on dates.

Though Ice reminisced over the good times with such reverence, he was, unfortunately, not smitten by the "Frozen on Fire" singer. "Were you in love?" Ice was asked on "The Dan Patrick Show." His answer was simple and clear: "No." As such, when the relationship finally ran its course, thanks to Madonna's erotic publication, "Sex," Ice moved on. He told News of the World (via NBC San Diego) that he was upset to see photos featuring himself in the coffee table book.

The early '90s were quite the trip for Madonna. In addition to dating Vanilla Ice and living it up with Dennis Rodman, she had a 15-month sizzling romance with actor Warren Beatty. Madonna and Beatty met on the set of the Beatty-directed crime-comedy flick "Dick Tracy," also starring Al Pacino, Charlie Korsmo, and Neil Summers.

When asked about intimate details, Madonna confirmed on "The Howard Stern Show" that Beatty — who'd gained notoriety for dating famous personalities such as actor Goldie Hawn — was a terrific companion. "Yes, he was [an incredible lover]. I'm not gonna lie," she said. Of his equally popular ex-lovers, she wasn't in any way intimidated (via Closer Weekly).

For his part, Beatty was intrigued by the work Madonna had put into making herself a household name. In a 2016 conversation with People, he remarked: "She's a huge personality, diligent and disciplined and a spectacular dancer and performer." The "Heaven Can Wait" actor further acknowledged Madonna's larger-than-life stature, praising her work in his film and saying, "She's a phenomenon."

While some of Madonna's exes have claimed that she was adamant about having children with them, that doesn't seem to be the case with Dutch dancer Timor Steffens. Back when the "Promise to Try" singer had just cut ties with Brahim Zaibat, a little birdie whispered to E! News that she was just having fun in 2014 and was not serious about dating Steffens. The pair had met in Switzerland, and theirs was a short and sweet affair that was gone just as fast as it came, per Us Weekly.

Just like his ex, Madonna, Steffens believes that age is nothing but a number. At least, that was evident in an interview with the Mirror. Steffens was nonchalant about their 30-year age difference: "There is an age gap between me and Madonna but I don't notice it," he said. "My girlfriends have always been older than me and that's how I like it. I learn a lot."

In addition to being inspired creatively by Madonna's music, one of the best parts of their brief relationship was hitting the gym as a couple. Her commitment was unmatched. "Madonna is so disciplined with the gym, which is great... she inspires me to go that extra mile," Steffens told the publication.

Musician Dan Gilroy may have taken things a bit too far when he agreed to a documentary that details his relationship with Madonna. According to Page Six, Gilroy was in the singer's life way before she reached superstardom with the hit song "Crazy for You" in the '80s. The documentary, titled "Madonna and the Breakfast Club" after the band Gilroy and the singer were in, was released in 2019. 

News of the production came as a surprise to the singer's fans, given that Gilroy had moved on. Since 1989, he's been with actor Shelley Duvall, whom he met on the set of the Disney Channel's "Mother Goose Rock n' Rhyme," per The Hollywood Reporter.

On the fun times he shared with his then-bandmate, Madonna, Gilroy considered it an escape by a whisker that he didn't push things further. According to Radar Online, he was of the opinion that he "dodged a bullet with Madonna," and doing life with Duvall through the years is a step up.

Promoter Peter Shue has memories of Madonna that are far from the adoration of her fans. Shue indicated on "This Is 50" that he did date Madonna, but it was a strategic move by his crew. "She's cool to be with, I ain't gonna lie, we had some good times, but she's not my type," Shue revealed. Asked to paint a picture of what it's like to physically be with Madonna — who the Independent still calls a sex symbol — Shue crassly critiqued her body when discussing their romance on Hot 97.

The promoter spent a couple decades in prison on drug charges, and he told the Daily News, "I was trying to get my money washed through her and maybe she was trying to get me locked up." Shue maintained that Madonna might have cooperated with authorities for him to be apprehended. 

Shue, who tried to sell the pop icon's underwear, added, "I would never socialize with her. I wouldn't want to hang with her. But I forgive her."

Although huge parts of Madonna's love life are open to all, she's only overtly spoken of her high-profile relationships. Antonio Sabàto Jr. supposedly dated the singer in the '90s, but Madonna seems to have never gone public with the romance.

Instead, he used the promotion of his memoir, "Sabàto: The Untold Story," to fill Access in on the details. Prior to meeting Madonna, Sabàto was already drawn to the entertainment industry. He had to get his finger in the pie, regardless of how that happened. "I was always infiltrating, going to parties, getting to know publicists and PR. I had just this whole thing and I was very motivated, " he told the outlet.

At a Janet Jackson music video shoot, Sabàto struck a bond with photographer Herb Ritts, who happened to be in Madonna's circle. "When I met her the first time, I didn't know it was Madonna," Sabàto explained. "It was very surreal... She was smaller than I had thought. She was a beautiful, beautiful, woman and all that but I just, before I met her she was just bigger than life," he added. The actor has reportedly dated Rachael Leigh Cook, Pamela Anderson, Jewel, Jennifer Love Hewitt, and other celebs; he launched a dating blog for men in 2013. Per his Instagram, Sabàto has rebranded as a realtor in Florida and is known for his Republican politics.