Madonna was married to Sean Penn for four years in the late 80’swhen he was at his Bad Boy worst. He was drinking heavily, getting into fights, and lost his driver’s license. One horrible Thanksgiving weekend he supposedly tied Madonna to a chair (“trussed her up like a turkey”) and tormented her for hours – including threatening to stick her head in the oven. She filed for divorce, but a few years later they made up and she started speaking to him again. Madonna might have some great advice tor Charlize about what to expect and how to handle Sean. Meanwhile Charlize seems to be picking up Sean’s bad habits – specifically his sour disposition.
(Above, Charlize is slumping so she doesn’t tower over her boyfriend)

Photo Credit: Pacific Coast News

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  1. These 2 were made for each other as they’re both miserable people.

  2. They are both ‘scraping the bottom of the barrel’. Both are desparate and found each other at their lowest point. I can’t see this pairing, but what the hell ever. Come to think of it, they are not too much weirder than all the kinky goings on in GollyWeird.

  3. She’s gorgeous, and he’d be hotter if he got rid of that creepy used-car salesman mustache.

  4. She also needs to talk to his last wife, Robin Wright Penn. THAT was an equally stormy union.

  5. I think they have charity and the movie business in common. She does a lot of charity work in South Africa and he does a lot of charity in Haiti. I don’t think they will have kids together and his kids with Robin Wright are now grown adults so he was alone when they hooked up. The same with her. She dated Stuart Townshouse for YEARS and then they broke up. I think they were two people who were out of long term relationships and fell in love. Nothing wrong with that. The Sean Penn from the 80’s is older now. They both have not had a hit movie in awhile, but both are Best Actor winners.

  6. I don’t think Madonna left her mark on Sean. I think Robin Wright left her initials engraved on him. Robin and Sean will always be connected because of their children. Sean reportedly laughed at Madonna at one of the Oscar parties when she showed up with her younger boyfriend. Sean that he was her son.

  7. She’s free to take a look at his track record and form her own opinion.

  8. Whoops, I meant it’s a toupee for pubic hair, not public hair. Damn auto-correct!!!

  9. @Glenda – LOL!!

    They are both good actors, if they’re happy good for them.

  10. in case the naysayers have forgotten madonna said…. on film …. sean was the love of her life….i believe it….

    the true love of most people’s lives are in the end a heartbreaking pain in the ass heart soul and only meant to last for so long before some one says
    so long…..

  11. All ‘great’ love affairs are in fact tragedies …look at Romeo & Juliet.

  12. But this is more like Ellen and Portia or Hillary and Huma

  13. They’re two flaming liberals. Congrats to them; they deserve each other.

  14. NO.. they are made for each other.. she’s the same bossy pants, smug personality type as him, but hid it better..

  15. Sean Penn is showing signs of over age 50 maturity. Because Charlize is Not a serial dater, maybe there is more to this coupling than a lot of (us) are ready to recognize. Who would have thought that SP would have taken such an active role in being one of the first prominent people on the scene after the Haiti Earthquake and devastation. Who would have bet that sex symbol Charlize would become a mother of a little boy that she appears to adore. Maybe this Oscar winning couple became acquainted at just the right time in their lives!!

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