Madonna dated this Studio 54 DJ, who produced hits on her 1983 debut including "Borderline" and "Holiday."
Madonna and Sean Penn married in 1985, at the height of her rise to stardom. Until their divorce in 1989, the often-volatile relationship attracted much media attention, and Sean faced legal troubles for run-ins with the paparazzi, while also pleading guilty to a misdemeanor domestic violence charge.
Madonna began a romance with costar Warren Beatty while filming the 1990 film Dick Tracy. Madonna's brother would later "tell all," divulging that she began dating the movie's director to help her career and even considered accepting his marriage proposal.
In the early 1990s, Madonna dated this former Calvin Klein underwear model. The pair mixed business with pleasure, as Tony appeared in some of her music videos and her 1992 soft-core coffee table book, Sex. She was also linked to another star of the book: Vanilla Ice. He said the book caused them to break up: "We were in a relationship yet it looked like she was screwing all these other people."
Perhaps NBA star Dennis Rodman was channeling Madonna when he infamously attended a book signing wearing a wedding dress. The pair were linked in the mid-1990s. Dennis would go on to dedicate pages of his autobiography to chronicling his sex life with Madonna.
On Oct. 14, 1996, Madonna gave birth to her first child, Lourdes Maria Ciccone Leon, after a relationship with her personal trainer Carlos Leon that began in 1994. They soon split after having a child together.
Madonna's taste for younger men showed when she hooked up with British director Guy Ritchie, although he's only 10 years younger than her. In August 2000 she gave birth to their son Rocco, and in December of that year they tied the knot in Scotland. Guy would go on to direct Madonna in the flop Swept Away in 2002. In 2008, the pair divorced and Madonna said she would rather get run over by a train than marry again.
As her marriage to Guy Ritchie ended, rumors surfaced that Madonna and MLB slugger Alex Rodriguez were hooking up. On Thanksgiving weekend 2008, her tour conveniently stopped by Miami, where ARod enjoyed the show from the front row.
Madonna watchers first got a glimpse of her chemistry with Brazilian model Jesus Luz when they posed together for a steamy W magazine photo spread in early 2009. The pair were still going strong on her last birthday, but alas it wasn't meant to be.
Madonna met 24-year-old French breakdancer Brahim Zaibat in 2010, when he performed at the launch of her Macy's clothing line. They're still going strong, and he's performing with her during her "MDNA" World Tour.