Madonna has a legendary music career. However, her love life is nearly as talked about as her songs. Over the last forty years in the limelight, she’s dated actors, models, sports stars, and more. In a shocking disclosure, an MLB legend claimed that she made him strip for racy photos. Keep reading to find out more.
Madonna’s Dating History: Oscar-Winning Actor, NBA Bad Boy & More
Madonna’s dating life was headline news throughout the 1990s after her marriage to actor Sean Penn ended in 1989. That same year, the singer began a short fling with Warren Beatty, her co-star in Dick Tracy. The Oscar-winning actor was featured in the Madonna: Truth or Dare documentary in 1991 but their relationship fizzled after that.

She went on to date some of the most famous celebrities – Tupac Shakur, NBA bad boy Dennis Rodman, and Vanilla Ice, to name a few. She welcomed a daughter, Lourdes “Lola” Maria Ciccone Leon, with Carlos Leon in 1996, but they split up a year later.
Madonna went on to have a second child with director Guy Ritchie. They married in 2000 but divorced eight years later. She was linked to Yankees player Alex Rodriguez before the ink on the divorce papers was dry. In recent years, she turned her eye to backup dancers half her age.
Madonna Made MLB Legend Strip For Racy Photos
Madonna and baseball player Jose Canseco were the talk of the town in 1991. An alleged rendezvous made him late for practice, fueling dating rumors. However, the MLB legend has maintained for decades that they were never romantically involved. In his 2005 memoir, Jose Canseco admitted to using steroids and claimed it was common in the MLB. He also discussed Madonna. He claimed that the singer aggressively pursued him and wanted to marry him.

The MLB legend opened up more about his time with Madonna. During an appearance on the Sources Tell Jeff Passan podcast, Jose Canseco claimed the “Vogue” singer made him strip down and pose for a “beefcake” book.
“Madonna [wanted] to see what I look like without my uniform on. So I spoke with [sports photographer Michael Zagaris] about taking some pictures, not nude but pretty close. Madonna wanted front view, side view, back view, whole combinations, just to see what I really look like, what she was getting herself into,” he claimed.
The former baseball player added, “She wanted me to marry her so she must have liked it. I was never attracted to her. Never wanted to do anything with her. She chased me around, called me at the clubhouse all the time.”
Madonna has never addressed what happened with Jose Canseco. But in 1992, she released a book of explicit photos with various celebrities.
