John Benitez, X-BF: 1983-1985
The two were introduced by previous ex Steve Bray, ouch. J.B. remixes singles and also worked with M. She clearly hasn’t lived and learned. Dump.
Sean Penn, X-Hubby: 1985-1989
Divorced due to their endless infamous fighting. The two are actually mucho alike: hotheaded, passionate and über-talented. Ironic that Penn actually turned into a better version of Guy, an award-winning director and actor. Whatevs, the arguments just lead to good makeup sex. Should've Stayed Together.
John F. Kennedy Jr., X-BF: 1989
Had a brief and steamy fling. Almost a match made in H'wood heaven—slutty pop royalty meets member of the closest family America has to royalty. Jackie O. was certainly just as formidable as Guy’s royal piss of a mother. Could've Stayed Together.
Sandra Bernhard, X-BFF: Sometime Around 1989
Ever wonder where Lindsay Lohan learned her tricks? M and S.B. were also “special” friends. Keeping their togetherness out of the spotlight could have worked for a while. But only for a time. ‘Twas a phase. Dump.
Warren Beatty, X-BF: 1989-1990
Both have equal legend status. But after seeing W.B. try to steal the spotlight from his wife at The Women premiere we know that wouldn’t fly with ‘Donna.
Dump.
Carlos Leon, X-BF: 1994-1997
Probably Madge’s most successful relaysh. No marriage, no divorce, no problem. And they’re still good buds, to boot. Plus, got a cute little tot, Lourdes, out of it. But C.L. teeters between being famous and invisible, the worst combo for a Madonna mate.
Dump.
Guy Ritchie: Soon-to-Be X-Hubby, 2000-2008
It’s tough to be Mr. Madonna, obvs. Guy had über-potential to be the indie version of Spielberg, but that ain’t gonna happen when you feature your wife-unit in your flicks. Better to get out now than prolong the inevitable. He’s clearly not content being No. 2 in the fam.
Dump.
Alex Rodriguez: 2008
Can almost see another S.P. romance brewing. A-Rod clearly is the Madonna equivalent in the sports world, but is he up for what comes along with it, like accompanying her through all her humanitarian efforts? Nah, just another fun fling. Dump.