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Madonna has a colorful—and extensive—dating history. The Queen of Pop has partook in a slew of high-profile romances, including her marriages to actor Sean Penn and filmmaker Guy Ritchie, her flings with baseball star Alex Rodriguez and Oscar-winner Warren Beatty, and her relationship with baby daddy and personal trainer Carlos Leon.

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"Yeah, tongue-in-mouth kissing [with Michael Jackson]…. I haven't had the chance to talk about it, no one ever asks me.

I did [make the first move on Jackson]…He's a little bit shy. I did get him to, sort of, loosen up with a glass of Chardonnay.

In 1991 she released her first studio album, entitled Excuses for Bad Behavior (Part One).

In 1995, she briefly appeared as a guest in the animated talk show Space Ghost Coast to Coast, in an episode titled "Jerk". She gave birth to daughter Cicely Yasin Bernhard on July 4, 1998.

She launched an Off-Broadway one woman show called Without You I'm Nothing, with You I'm Not Much Better in 1988 which played at the Orpheum Theatre.