Charlize Theron & Sean Penn ‘made out like crazy’ at Madonna’s Oscar party

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I was really, really hoping that Charlize Theron and Sean Penn would come to the Oscars together. I knew Charlize was presenting, and I just thought – “Hey, that would be really interesting to see them make their red carpet couple debut at the Oscars!” But it was not to be. Charlize brought her mom Gerda to the Oscar ceremony, then Charlize was strangely absent from all of the major after-parties. No Charlize at the VF party, no Charlize at Elton John’s shindig. So, did she just go home with her mom? Of course not. She dropped Gerda off and then Charlize joined Sean Penn… at Madonna’s Oscar party. Partying at your boyfriend’s ex-wife’s Oscar party? Oh, dear. And it totally gets worse:

Leave it to Madonna to be a good sport. As per tradition, the pop legend, 55, hosted her annual Oscars after-party on Sunday, March 2 at the L.A. mansion of her manager Guy Oseary, with festivities raging from 10 p.m. to around 6 a.m.. Among the night’s many, many A-list guests were her ex-husband Sean Penn and his girlfriend, Charlize Theron.

Fellow Oscar winners Penn, 53, and Theron, 38, were “making out like crazy” and “all over each other” on the dance floor, an observer at the bash tells Us Weekly. “They were the talk of the party — even Madonna noticed!” Penn and Madonna divorced way back in 1989; she eventually married and divorced Guy Ritchie, while he divorced Robin Wright after 14 years in 2010.

Still, the former couple’s four-year union was passionate, and the Material Girl’s close pal Debi Mazar recently quipped that Penn remains Madonna’s “one true love.” Over the years, Penn was supported his ex-wife at concert performances, and she recently joined him in Haiti on a humanitarian project.

Regardless, Penn and Theron’s makeout session was on display for all to see — including attendees Julia Roberts, Nicole Richie and Joel Madden, Brad Pitt and Angelina Jolie, Miley Cyrus, Tom Ford, Ellen DeGeneres and Portia De Rossi, John Travolta and Kelly Preston . . . even Madonna’s teenagers!

Past 2 a.m., “Madonna was dancing up a storm with her kids Lourdes and Rocco on the dancefloor,” the observer says. “She kept walking around the party trying to get everyone to dance.

[From Us Weekly]

Ordinarily, I wouldn’t even think “Poor Madonna” about anything. Madge does not need anyone’s sympathy. Madonna sees empathy as weakness. The Gristle will crush your sympathy!! But I felt a wave of sympathy for her here. I believe that Madge and Sean Penn still have unfinished business with each other, and it feels… cruel? Like, Sean and Charlize could have gone to any after-party. But they went to his ex-wife’s party and they made out like crazy and Madge “noticed.” Must have been hard. Or maybe I’m just projecting. Even if you know intellectually that you shouldn’t be with someone ever again, there’s still some residual stuff. And Charlize… well, she’s tall, young, beautiful and making out with Madonna’s ex-husband, the man Madonna once called the love of her life. Rough stuff.

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Photos courtesy of WENN, Fame/Flynet and Madonna’s IG.

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103 Responses to “Charlize Theron & Sean Penn ‘made out like crazy’ at Madonna’s Oscar party”

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  1. Jayna says:

    Madonna’s party is very exclusive. Madonna invited them and obviously wanted them there, so I’m sure it’s all fine.

    I wish I could see Madonna’s whole dress. I like the red on her and I love her headpiece. I read it was $100,000 worth of diamonds. I saw a photo of her hands and know what the issue is. It’s not that her hands look old from being wrinkly. I saw her hands in 2006 and they looked fine. But it’s her veins that are the problem now I guess. I saw an photo from a few years ago and she has bulging veins all over her hands. My mother had the problem with prominent veins on her hands, and I have some visible veins on my hands. Is that what is going to happen to me? Poor me.

    • Lily says:

      I agree there is no way they would have gotten in or stayed if Madonna didnt approve of their attendance

    • Dustyfoot says:

      Yep. They were there because Madonna wanted them there. Besides, its been 30 years already. What psycho would still be miffed over their ex kissing someone after 30 freaking years? Even if Madonna is that level of psyco, its pretty clear that she and Sean have worked out their issues.

    • Suzy from Ontario says:

      Love the red dress too! Looks goregous and the colour looks awesome on her! As for Sean and Charlize…I think it’s tacky and pretty highschool for any couple to go to a party and then *make-out* or be all over each other. Attracted or not, it’s just kind of immature and stupid. I mean, skip the party and get a room if you can’t wait. Thought Charlize was smarter than that, but lately my opinion of her intelligence has dropped significantly.

    • The Original G says:

      I have to admit, I do wonder about Madge’s hands? Could they really be that bad? The gloves are just ugh.

      • Moi says:

        My mother was beautiful, truly beautiful, and so youthful looking with no plastic surgery, until the day she passed away suddenly at age 64. She had wrinkly old lady hands. My 17 year old has them too. Hands truly do not convey age, yet they are perceived to. I received half and half. My hands can look older than I am at times (I feel so anyway), but in pics, look like smooth, long piano playing hands. My mother was small like Madge and my daughter. I am long and lean. My point being, hands have nothing to do with age. That is a misconception. My daughter is proof of that. Madge feels self conscious about her hands, like my mother did also. Due to the above misconception.

        If Madge gave two shits about SP and CT, she would not have invited them.

  2. David99 says:

    What is Charlize thinking or not thinking???

    • LadyMTL says:

      I’ll go with not thinking, due to the hormones and all that stuff. Personally the very idea of making out with Sean Penn makes me want to join a convent…Charlize, you can do soooo much better!

      • Aussie girl says:

        Everythink I thought about her has changed. She has lost me

      • Isadora says:

        Pretty much. I remember thinking she was one of the few female actresses in Hollywood I really respect and like because she was not over-eager and pretentious, but really laid back, funny and overall great.

        However recently I wonder…

        +1 on the convent comment @LadyMTL :-D

    • Jaded says:

      She’s dickmatized….regardless of how horrible a person Penn has been, apparently he’s da bomb in the sack.

      • Sumodo1 says:

        Yes, and EWWWWwwwwww!

      • DrM says:

        Having been dickamitized myself I get how this can happen. That level of sexual combustion causes your rational brain to pack a bag and leave the country….just sayin’!

    • whewwy says:

      Ewww! Just Ewww. She went off her rocker a few years ago.

    • Sarah says:

      She’s not thinking and it’s going to end badly and I really hope no one is physically hurt in the process….:(

  3. poppy says:

    making out at anyone’s party is attention whorish. especially when you’re over 30.
    go home or get a room.
    her partner of choice, blech.

    • Eva says:

      Yeah, she’s gone way down in my estimation, very cheap and tacky behaviour.

    • Kiddo says:

      I don’t think Madonna cares, she’s long over him. Madonna is attention-whorish, so it seems like, if any party, hers would be the most appropriate for it.

    • MissNostalgia says:

      Exactly! Gross…just gross.

    • Kosmos says:

      Agreed, they’ve had plenty of time to ogle each other recently, so going for it publicly at a big event like that is totally saying, Look at Us !!!! I’m actually kind of surprised at Charlize…..because otherwise, she seems to have better manners.

  4. Eleonor says:

    While I sort of get Sean Penn behavior, I thought Charlize was better than this.

  5. stellalovejoydiver says:

    Ewwww and that `s really tactless

  6. emmie_a says:

    I can’t remember where I saw this story but supposedly Charlize had a big party benefitting her charity where people paid thousands of dollars for their tables but it was a total mess. They ran out of food, the bathrooms were gross, the entertainment was raunchy, etc. Any truth to this? And did she even show up to her party?

  7. Lilacflowers says:

    Charlize and Sean are way too old to be acting like horny teen-agers at a party. How disrespectful to any hostess. And couldn’t Charlize have managed even the tiniest of smiles when she was presenting at the Oscars? She was standing next to Chris Hemsworth, for God’s sake! Most women would manage to at least smile at him instead of that scowling pout she adopted.

    • Sarah says:

      She may have been the worst presenter of the night…she missed her line and just seemed really awkward and uncomfortable. She’s lost confidence or something?

  8. Maya says:

    God I would have loved to see a bitch fight between Madonna and Charlize – I have no idea who would win.

  9. Ellie66 says:

    To bad Madonna didn’t cut a bitch! ;) Lol!

  10. Lark says:

    I can never get over how there is a freaking police report (not gossip, an actual report) about how he beat the shit out of Madonna (and it’s insinuated sexually assaulted her too), and yet she brings her children around him and invites him and his new girlfriend to her parties….So bizarre. I can maybe get them being civil, but they seem like they are close friends…and before someone gets into something like Jack Nicholson and Anjelica Huston being tight (Jack cheated on Anjelica and knocked someone up while with her)….I think that’s a bit odd too, but there’s a huge difference between cheating and committing a crime and physical abuse.

    Meh. He and Charlize seem like they are truly in love (and that’s another bizarre match). I’ve never seen old leatherface look that happy before.

    • Virgilia Coriolanus says:

      Do you have a link to the police report? Because when I looked up the whole ‘Sean Penn hit Madonna over the head with a baseball bat and kept her captive for three days’–all I came up with was an excerpt from a book written by one of her former managers–talking about it. And from that, I got that there WASN’T a police report because Madonna wouldn’t press charges.

      • Div says:

        I remember that mess. In California, the cops will file a report without the victim or something along those lines if they see abuse but she initially cooperated. I’m an old, and it was a huge deal in L.A. and was covered by the local news & L.A. Times. I believe he was charged with Felony Domestic Assault and managed to plead down to some bs charge or have it dropped because Madonna stopped cooperating. As an old, I can’t cut and paste on my I phone but if you Google Sean Penn Felony Domestic Assault L.A.Times there should be some articles. It was a big deal, and the original charges were a felony before he got it pleaded down or dropped. The fact that the cops actually charged a wealthy, powerful actor instead of giving him a pass was telling.

    • Isadora says:

      I guess the only reason for ever overcoming such a thing is if the perp was totally drugged out of his mind back then and is sober now. Which was maybe the case with Sean Penn, he certainly looks the part….

  11. Merritt says:

    Given the abusive nature of Charlize’s parents relationship, it makes me sad she is now with a known abuser.

    • Maggie says:

      That’s crossed my mind as well. I don’t get it.

    • Liberty says:

      yes — this is the strangest part of the whole thing, IMO.

    • Nerd Alert says:

      Yeah. I doubt Madonna was in jelly school over their makeout sesh, but I think we are skimming over the really sad, possibly foreshadowing nature of this relationship. When you think about it, who really GAF if Madge was slightly put off?

  12. India says:

    Sean Penn is without a doubt the most unappealing man I have ever seen.

    • psst! says:

      Woody Allen begs to differ

      • booboolarue says:

        LOL! Both extremely gross. . .not even if one of them was the very last male on earth.

      • amy says:

        Seriously, someone has to start to remember on every Penn post or article related, the fact that he’s a documented woman’s beater, even if Madonna will never speak about it, saving his career (if she had charged pressed he would never would won Oscars, not even be working again) but HAS to be acknowledge the fact that he’s not anyone to be praised, not even the humanitarian work (which I think is just for publicity) would save him from public shame.

  13. blue marie says:

    I think you might be projecting, Hamface is out of her age range now. I was really hoping the glaze would rub off and Charlize would realize he’s not for her but.. she’s an idiot.

  14. Vee says:

    They are both very prickly personalities. They may not match physically, but ideologically they are perfect for each other.

    • bns says:

      Exactly.

    • amy says:

      It makes sense, Both Madonna and Robin Wright are rather prickly. But at least both of them are getting f-cked now by young studs (in Robin Wright’s case fiancé Ben Foster is yummy much), as for silly Charlize, she wakes up every morning with a baked ham by her side.

  15. Assistant Rachel says:

    Eeewww!

  16. jj says:

    She’s a beautiful woman, but I get a bitchy vibe from her!

  17. bns says:

    To be a fly on the wall at those parties…

    • Nicolette says:

      +1. One can only imagine what goes on.

    • Ellie66 says:

      I remember all the drama when Madonna and Sean got married and when he beat her and tied her up, this was before the internet so not every little detail was known (to me) where do I see I police report?

  18. serena says:

    Dear…. I don’t know what do these gorgeous and talented women find in Sean Penn.

    Other than that, I kind of cringed reading Angelina Jolie and Miley Cyrus names next to each others. Ugh!

    • lower-case deb says:

      that’s probably the closest they’re going to get?

      i wonder if any of the Jolie-Pitt kids like Miley as a pop idol. Maddox was at the party allegedly?

      do they? or not… especially since they’re often seen wearing heavy metal band shirts.

      speaking of JPs, what level of making out were Charlize and Penn at? AJ and BP were often touchy feely (but grabs, pda) on events… was CT and SP just being “pitt porny” and Us Weekly blowing it out of proportion?

      • Maya says:

        “speaking of JPs, what level of making out were Charlize and Penn at? AJ and BP were often touchy feely (but grabs, pda) on events… was CT and SP just being “pitt porny” and Us Weekly blowing it out of proportion?”

        I seriously don’t need to find out how gross Sean and Charlize were – thank god no description were written otherwise I would have to develop selective memory loss.

    • Maya says:

      Thank god it was a false rumour about Angelina and Brad attending and even to be linked with Miley is puke worthy. Angelina and Brad skipped all of the popular after parties and instead went to an restaurant for an exclusive dinner with rest of the 12 years of slave cast and some few close friends.

    • JP fan says:

      Jolie and Pitt party at Ago Restaurant

      • Shiv says:

        Could have went after AGO restaurant as I know Lupita and Cumberbatch were at the Madonna after party and they were at AGO first. Lupita’s brother is an Instagram user ;)

  19. Nev says:

    People can and sometimes do FORGIVE people when they make mistakes. DUH.

    • Isadora says:

      I wonder if being hit in the head with a baseball bat and being tied up can be termed a “mistake” hm…

  20. Dhavynia says:

    I always liked Charlize, always liked Madonna and heck I even like Scarlett but I’ve always been puzzled by the Sean Penn attraction. Forget the fact that he looks like the male version of Magda from TSAM but he seems so controlling with a shitty temper and these women seem to be very independent, won’t put up with any bullshit women.
    I always wondered how Robin made it all those years even though he seemed a little tamed while they were married.

  21. Nicolette says:

    I’ve always felt Madonna and Sean will wind up together again some day. She has repeatedly said over the years that he is the love of her life and I’m sure Charlize is well aware of that. Perhaps she is not quite so secure and confident in her new relationship and felt the need to put on a display as a way of making some sort of statement that he is with her.

  22. Lori says:

    All three of them are Leo’s………..can’t imagine that much ego in one place!

    • PunkyMomma says:

      ^This. Huge egos. Whether you care for them personally, or not, all three are tremendously talented people. I totally agree that Madge will always have a lady boner for Penn. It wouldn’t surprise me one bit if Madge, Sean and Charlize ended up in a threesome at some point.

  23. epiphany says:

    I think Madonna continues to carry a torch for Sean; he’s the one area of her life where she remains vulnerable. I don’t think she’ll ever really be over him. I’ll bet seeing them together hurt, not that she’d admit it.

  24. Micah says:

    Is this REALLY an issue.

    Seriously.

    Madonna and Sean Penn divorced…in….

    1989!

    I seriously think both parties have moved on.

    • PunkyMomma says:

      I respectfully disagree. Madonna stated in an interview that when she gave birth to Lourdes (via C-Section), prior to the delivery she had been on the phone with Penn. Penn has a piece of her heart to her grave.

  25. Meme says:

    Aren’t they a bit old for this? Used to love charlize but now she’s acting like an a-hole.

  26. toto says:

    Not good to imagin yuck.

  27. Suze says:

    “Made out?” At someone’s part?

    Are these people adults or fifteen year olds?

  28. dizzylucy says:

    Ugh, I really don’t understand this relationship at all, and that just sounds lame.

  29. Happy21 says:

    I am shocked that Debi Mazur and Madonna are still friends! Madge doesn’t seem to keep friends…

  30. Lila says:

    Why is she taking Robin Wright leftovers? Penn is so ugly and old, Charlize should do like Robin did and ditch him for a young hot piece like Ben Foster, not jaded and easy on the eyes.

  31. Lila says:

    Besides, these two are parents: Penn has two adult children and Charlize has her little adopted son, I should be ashamed to have a father that behaves like a sexed up animal in front of everyone.

    • taxi says:

      Were you there? How do you know? Kissing during a slow waltz is making out, although I doubt madge’s sound people were playing slow-dance music. “….sexed up animal” is pretty extreme.

      • lila says:

        Waltz? What r u talking about? Were YOU there? The reports says “making out like crazy” why don’t you question the reports? Are you a Penn freak? Get a life, this is a gossip site.

  32. Grant says:

    This reminds me so much when he was dating ScarJo, they desperately try to show the word they were together making out even at the White House Correspondent Dinner. Tacky!. A few months later the heat went away and they broke up. I think Penn is trying desperately to show the world how a heartthrob he can be, and that he’s a ladies man, he loves that kind of attention, narcissistic egomaniac type. I think is a symptom of a middle life crisis and a nasty divorce that he didn’t got over yet. (and maybe it hurts seeing his ex wife truly moving on with a man 20 years his younger)

    • Naty says:

      Absolutly: middle life crisis for Penn, making out in public like two horny adolescents is a sign of a show off kinda relationship, this guy has issues. ScarJo all the way. Charlize, you introduced this creepy guy into your kid’s life, you’re gonna regret it. You’re desperate for a man to father your adopted son, but this guy is just gonna play with you. He’s still into his ex-wife Robin

      • hmmm says:

        Viagra has to be involved. No way is he the swordsman of old. That must be a pretty sight.

  33. Hugh says:

    Wow, what a classy lady! From Penn that nasty dog nothing surprises me, but Charlize is ruining her reputation, if she had any.

  34. Lux says:

    I’ve always been indifferent towards Charlize but she was making such bitchy prima donnaish faces during the Oscars I just can’t with her anymore.

  35. amy says:

    she’s being pap going to the gym almost everyday but seems not being able to build any muscle at all.

  36. Meinu says:

    Honestly if Charlize wants to be another girl on his abuse list, then that’s her choice. But I just want to say this “Charlize, stop tweaking your face!!” She’s starting to look like a copy of Charlene of Monaco. Do they share the same surgeon?

    • FingerBinger says:

      Charlize is not tweaking her face. She’s got visible lines around her eyes. She’s aging naturally, unlike many others in Hollywood.

    • amy says:

      I think she’s definitely having some subtle work done. bad work that is. her eyes look asymmetrical.

    • Naty says:

      You cannot say she hasn’t have work done looking at the second picture. Starting with a nose job from years ago and going on with botox and fillers. Got to be blind to not seeing that.

  37. Naty says:

    Wow, that’s all the info I needed to know that this fling is not going to last, is gonna be like the ScarJo thing, a couple of months. You don’t make out if front of half Hollywood with a woman you really respect and care about.

    • FingerBinger says:

      Some of these comments on here are so silly. “You don’t make out if front of half Hollywood with a woman you really respect and care about.” It wasn’t half of Hollywood and it was a private party,where you couldn’t even bring cameras. He’s kissing her in public so that must mean he doesn’t really respect her? Huh? That’s quite a leap. At the beginning of a relationship some people are very affectionate. I don’t get what the big deal is. Why is everyone reading so much into this?

    • hmmm says:

      The making out is really significant. How old are they?

  38. The Chaz Gomez says:

    I have two things… One… Of course this didn’t bother Madonna. It’s been a whole bunch of years since she and Sean Penn were together. We all know how much of a freak she is, she was probably watching and taking videos… And Two… Charlize and Sean Penn together? This makes me very sad. Cuz, Yeezus!!! That dude is frickin’ ugly…

  39. FabsBingo says:

    I had no idea she was with Penn in the first place. What a shame, she is a great actress and I really dont rate him…