Madonna did a lot of outrageous things in the 1990s, but one that was perhaps forgotten? Her brief but headline-grabbing relationship with basketball legend Dennis Rodman.
Despite the fact that their time together was short in the grand scheme of things, quite a few intriguing details have emerged over the years — many of them from the mouth of Rodman himself!
So let’s look back at their whirlwind romance…
How It Began
The early ‘90s wasn’t the best era for Madonna, career-wise — her 1992 album, Erotica, was her least successful, and her 1993 movie Body of Evidence was poorly-received, too. So, a new romance was just the pick-me-up she needed and Rodman, on the up playing with the San Antonio Spurs, was a great choice.
According to Rodman, Madonna set her sights on him from afar in 1994. In an interview on the “In Depth With Graham Bensinger” podcast in 2025, Rodman said that he first heard that Madonna was interested in him when she said on TV that “she thought Dennis Rodman was cool as f*** and wanted to meet him.”
Dennis Rodman’s Dating History: Madonna, Carmen Electra and More
He added: “She was chasing me in San Antonio … every day I go to practice, ‘Dennis, Madonna keeps calling for you!’ I say, ‘Who?’ They say, ‘Madonna.’ I say, ‘The singer?’ I just kept blowing it off. Next thing you know she actually showed up.”
Most people would be seriously starstruck by the Queen of Pop rocking up at practice, but not Rodman. “What, I’m supposed to jump up and down because it’s Madonna?” he said. (Well … kinda?) “I wasn’t even thinking about her. I thought her music sucked all bubblegum and s***.”
Ouch.
But he came around eventually, and the romance began when she came to one of his games in Los Angeles. “She was sitting in the front row with her friends, looking all Madonna-ish,” he said. “After the game, she’s sitting at my locker. I was like, ‘What the hell are you doing here?’ I didn’t invite her. She just came in and sat down. And all the players were like, ‘What the hell is she doing here?’ They didn’t care; they had their towels on. They just wanted their picture with her. He continued: “She was not shocked, she was just laughing, talking with the guys. And I went back to her house.”
Sounds like these two definitely knew what they wanted.
Remember When Madonna Stole the First VMAs Debuting ‘Like a Virgin’?
How Long It Lasted
This wasn’t an epic love story, it was a hot fling, and was over within a few months, with Rodman later saying in his 1996 memoir, Bad As I Wanna Be, that the relationship was “easy.”
He also claimed, however, that Madonna had been desperate to have a baby with him. He recalled a time when he was away gambling in Las Vegas, alleging that she had offered him $20 million to father her child.
“I picked up the phone and Madonna was like, ‘I’m ovulating, I’m ovulating. Get your ass up here,’” he wrote. “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 hasn’t commented on this wild anecdote.
Madonna Asked ‘Dear Friend’ Rosie Perez to Hook Her Up With Tupac Shakur
How It Ended
They had fun while it lasted, but ultimately the whirlwind romance crashed and burned — and Rodman put it down to differences between them and his worries that being with such a huge star could overshadow his own success.
“I still think of myself as this guy who had to claw his way up from a job as a janitor to get anything in life,” he admitted in his memoir. “So to be making a decision on how serious to get with Madonna was more than I could handle.”
What They’ve Said About Each Other
Madonna has never really said a word about the romance — but Rodman has more than made up for it.
“Sex with Madonna wasn’t wild, crazy, and kinky,” he said in his memoir. “It was just very entertaining. She wasn’t an acrobat, but she wasn’t a dead fish either. Madonna talked all the time about having a baby. I think she wanted every bit of Dennis Rodman — marriage, kids, everything.”
He added: “We came together in the perfect time. She was stagnating in her career, and I was coming up. We helped to motivate each other, going in the same direction at that particular time.”
Madonna’s Ex Jenny Shimizu Felt Like a ‘High-Class Hooker’ When They Dated
Looking Back Now
More than 30 years on, the brief fling still gets brought up in interviews with Rodman from time to time. In a 2025 podcast interview with Joey Dimodica, he said, “I don’t like talking about it too much but me and Madonna had a good relationship. We had a good friendship and we dated for a minute and strangely enough, she used to come in the locker room and just sit there. But it was no big deal. Guys just let her sit there… I used to go hang out with her. So I go to practice the next day, fly back to LA, whatever. This same old, same old… but it was cool.”
He went on: “In 1993, I think her career was declining, and she said the reason why she dated me was because I was a bad boy.”
Key Relationship Takeaways
There’s one takeaway that Rodman is eager to refute — many people believe his time with Madonna is what inspired him to start experimenting with outrageous hair colors and fashion, but he insisted this was all his own doing.
“We had a nice little fling,” he told USA Today in 2019. “That came and gone. Madonna didn’t influence me to be a fashion and creative guru.”
And since the fling, Madonna and Rodman have been very busy — both in work and love. Rodman was married to Carmen Electra from 1998 to 1999, and Michelle Moyer from 2003 to 2012. Plus, in 1996, he famously put on a wedding dress and said he was married to himself — which kind of sounds like something Madonna would do. He’s since been in a relationship with rapper Yella Yella, 31 years his junior, since 2022.
Madonna is no stranger to age gaps, either. Since her eight-year marriage to Guy Ritchie ended in 1998, she’s dated a string of younger men and, as of 2025, is in a relationship with football coach Akeem Morris, 38 years her junior.
