Madonna posts vintage photo of herself & Sean Penn on her Instagram: ugh?

2 rebel ❤️'s on a couch.

A photo posted by Madonna (@madonna) on

Last Friday, we discussed Sean Penn’s ongoing defamation lawsuit against Lee Daniels. Daniels name-checked Penn in an interview, calling out Penn for being an abuser of women. We all got the reference, considering there was some decades-old stories about Sean and Madonna’s relationship. Well, Sean and Madonna have become late-in-life friends, and Madonna thinks so much of her ex-husband that she submitted a declaration for Penn’s lawsuit. She basically says that Sean never physically assaulted her during their marriage. Then, over the weekend, Madonna posted this vintage image (above) on her Instagram.

I have a question: what is Madonna’s goal here? Do you think she and Sean Penn are “back together” to some extent? Are they merely friends now? Is he withholding and she’s trying to win him back? I feel like there’s some kind of angle at play here and I can’t quite figure it out. I think Madonna still has the potential to be a fool in love, so is Sean just using her foolishness against her for his own ends? Hm.

Meanwhile, Madonna has completed the European leg of her Rebel Heart tour. She performed in Glasgow last night and it was chaos. Honestly, I’ve read some reports that the whole tour was rather shambolic, that Madonna and her team were perpetually late, that the computers were always on the fritz, etc. As for last night’s show, the venue cut off Madonna’s power “without notice” because she stayed longer than they were expecting. Madge apparently sang a cappella in the dark for her fans. Afterwards, she posted this:

We don't stop till its over Glasgow! 🎉💃Don't try to silence the Queen👑 ❤️#rebelheartour

A photo posted by Madonna (@madonna) on

Photos courtesy of Instagram, WENN.

You can follow any responses to this entry through the RSS 2.0 feed.

40 Responses to “Madonna posts vintage photo of herself & Sean Penn on her Instagram: ugh?”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. t.fanty says:

    My take? She’s still halfway in love and he likes the fact that she sees him as he likes to imagine himself. I’m sure she “gets” him and they both think that’s a bit special.

    It’s strange to think that Madge could he such a cliché.

  2. Santia says:

    Madonna is still enamored with this prick.

  3. littlemissnaughty says:

    She probably doesn’t want to be the victim. Let’s not forget, this is the Image Queen and losing control like that is probably the worst for her. And being reminded of this mess so many years later is probably no picnic either. I have to say, it really should be her decision whether we hear the truth or not. But she’s going a little far, it’s turning into a rather gross performance. I don’t think they’re getting back together btw.

  4. Talie says:

    I seem to remember in her brother’s memoir, he also spilled tea about the abuse of this relationship.

    • V4Real says:

      Now she wants to take it all back. Why? Is it because they’re friends now or is she still a bit in love with him?

      • Wentworth Miller says:

        If they are friends now, I would think that would be the main reason she tells the truth about the abuse.

  5. bella says:

    Of course she’s still got a thing for him.
    They were married at a young age when “love” is very powerful, no matter how toxic.

    I find her posts childish and not how one would imagine the “Madonna” of past fame and trailblazing would behave in middle age.

    • mc says:

      Madonna was 27 when they married. She is older than Penn and had several long-term relationships before him – some of which lasted longer than their two-year marriage! She strung Dan Gilroy and Jellybean along for years then married Penn within months of meeting him probably because she was insecure about being labeled a swingin’ spinster. She filed for divorce in 1987, it just wasn’t finalized until ’89 because she temporarily withdrew the papers in an attempt to reconcile. Penn got a huge payout from her, which is why he was so hesitant to remarry even after he fathered two children by Robin Wright. He’s just as bad as Guy. Selfish men hogging their divorce settlement money.

  6. Jenns says:

    Remember in the Truth or Dare documentary how Madonna admitted that he was the love of her life? I think she still holds out hope for him.

    • Sayrah says:

      I was going to post about this too. She seemed almost in tears when she answered. But in a sweet way, not sad way.

  7. FingerBinger says:

    Madonna posted a vintage photo in august before the lawsuit. If it’s friendship or something else it doesn’t have anything to do with the lawsuit.

  8. NeoCleo says:

    Is Madonna suffering from Stockholm syndrome?

  9. Catelina says:

    It’s not the first time she’s posted an old picture of him in recent months so I agree it’s not about the lawsuit. I think she’ll always be a bit in love with him even if they haven’t ever gotten back together post divorce or if they never do. They seem to have grown quite close the past few years.

  10. Ally8 says:

    He looks like a short-fused doofus even in that photo.

  11. als says:

    I think for Sean Penn the lawsuit and the stuborness of defending his reputation and the rekindling of his relationship with Madonna, it all goes back to the stuff with Charlize.
    For Madonna it’s probably something else.

  12. Melody says:

    It’s hard to forget those powerful teens and 20’s feelings – and the people we had them with. I almost wonder if it’s the person or those feelings that people chase after when they’re old enough to have learned better.

    I met my husband at 33 – I’d love one night with him and my younger hormones.

  13. Bluesky says:

    Wouldn’t that be something? Madonna ACTUALLY having an age appropriate relationship?

    • Ankhel says:

      I can’t see it, Sean Penn goes for women in their thirties and early forties these days. She probably believes he might fall for her again anyway. I don’t think she’s very realistic about men and relationships, or about her own age for that matter.

  14. Bettyrose says:

    In other news, why is she trying to bring back hair parted in the middle? Just, no.

    • SydneySnider says:

      It seems to have been back for a while. It’s like every girl and her chihuahua is doing the middle-hair-part thing. I don’t think it’s at all flattering after a certain age. C. O. M. M. O. N.

      • Bettyrose says:

        I’m not sure it was flattering on me in my twenties but I rocked that look in the 90s like no one’s business. Curly locks and all. Never. Again. That look needs to crawl into a hole and disappear forever.

  15. EM says:

    desperate

  16. Mimz says:

    … I can barely form an opinion on this MESS but, He always grossed me out for those “alleged” beatings and My love for Madonna died many many years ago.
    Even if it’s just friendly support, it seems a little weird, a little “don’t hurt my forever crush” type of thing… They probably aren’t together but this is fishy to me.

    Nothing worse than never getting over your first love.

  17. Luca76 says:

    Yes but that abusive prick Sean Penn basically said that their marriage didn’t count right when he was engaged to Charlize he said that would’ve really been his first marriage. (I know the intended victim of the barb was Robin Wright but still).
    Btw I’m calling him abusive because even if the allegations are being denied he’s been verbally abusive towards Robin W for years on a public level.

  18. Kelly says:

    I hope they are back to together as it will save two more people from the horror of their company. Downside is their toxicity does not just double when they are together. It multiplies exponentially. Yuck. I am just their age, and they were insufferable back in the 80s and time has not been kind.

  19. Sochan says:

    Seriously, are they screwing? I honestly can’t imagine why she’s all up in his grille these days unless they’ve reconnected romantically and she’s prepping for a big reveal.

  20. Edward says:

    Her brother Christopher confirmed it in his awesome book “My Life With My Sister Madonna.
    He described in detail how he once had to rescue her when she called him after after she was beaten by Sean.

  21. Nouveau says:

    “I have a question: what is Madonna’s goal here? Do you think she and Sean Penn are “back together” to some extent?”

    I think she, like anyone else, gets to that stage when mortality makes you nostalgic and more forgiving. Also, she’s massively into the kabbalah and self-help so maybe that’s part of it too.

  22. Joh says:

    She filed a sheriffs report on him back in 1988.
    Was she lying then?
    Or now?

  23. nicole says:

    I think she is truly still in love with him, I would say she would take him back in a sec. Women are always drawn to bad boys.

  24. iheartgossip says:

    Oh MeeMaw Madge, give it up. We now know the truth: You were a big fat liar then, or you’re a big fat liar now. Either way, have a seat.

  25. mrsrockstar says:

    I remember clearly when they were together all the drama and public confrontations between Sean Penn and everybody and especially the press. But I also remember thinking and feeling that these two related on equal ground and seemed real with each other in some ways so different than the relationships I know came after. She is a talent and I in no way am criticized the train of younger men thatcame after but in those she had control with more power. This with Sean Penn may have imploded but I think that this was very much a real love affair.

  26. Debutante says:

    No UGH to the pic. Cute !

    • Anne tommy says:

      Sean’s a good actor. Madonna is a consummate self-publicist who has made a fantastic career out of a less than fantastic talent. I don’t know what happened between them. They do, but despite a supposed Sheriff’s report, our views are really just conjecture.

  27. christina says:

    I like her, but does she think we buy that her roots are brown?

  28. deehunny says:

    it’s not cool that she was late, but how awesome is it that she stayed and sung in the dark for her fans? That’s a true performer.