Sean Penn felt like he was ‘dying’ when married to a ‘Love Island’ & RHOBH fan

The New York Times’ columnist Maureen Dowd was sent to Malibu to interview Sean Penn, and this does not belong in a NYT column, first of all. This is just a straight celebrity profile, not a column. Second of all, I was like “why the hell do we need to hear from Sean Penn again?” He does have a new movie coming out, so that’s why – this is actual film promotion. He appears in Daddio, with Dakota Johnson, and it’s a little indie film where he plays a cab driver and Dakota is his passenger. Dowd’s piece is interesting for the typical celebrity-profile stuff, like the description of his Malibu home and his art collection. Penn’s politics are… what they are. There’s some interesting gossip too – he talks about Madonna and Robin Wright, he talks about his new friendship with Hunter Biden, and a lot more. I kind of think Ol’ Hamface has chilled out a little bit. Some highlights:

His friendship with Hunter Biden: He said the two met in 2022 when Penn gave a speech in honor of U2 at the Kennedy Center Honors. He had read an interview with Hunter, the first “since the chips were rolling down, and I was really taken with him and I told him.” Then last fall, after a screening of his Ukraine film with big shots on Capitol Hill, Penn had dinner with his friend Representative Eric Swalwell of California, who suggested he look up Hunter in Malibu. “I had no idea he lived down here,” said Penn, adding dryly: “I thought he was off in some judicial-focused place that we see on TV.” He called Hunter “a very, very insightful guy.”

He went to the White House state dinner for President William Ruto of Kenya last month. “Hunter invited me,” Penn said…“I left the president alone because there were opportunities for that when everyone is not tapping his shoulder.” He thinks Biden should “take it slow” in the campaign, leaning into an elder statesman role, doing fireside-chat kind of talks, not getting into nasty spats with Trump but giving the nation a sense that red and blue can be united. Of Trump, he said dismissively: “He’s shameful as an art and as a way of life.”

He stopped acting for a while because he was disillusioned with Hollywood. “I went 15 years miserable on sets. ‘Milk’ was the last time I had a good time.”

Whether he thinks he could play a gay character today: “No. It could not happen in a time like this. It’s a time of tremendous overreach. It’s a timid and artless policy toward the human imagination.”

It sounds like he is just burned out: “I feel like an actor who is playing a leading role and is a known actor and is being paid well has a leadership position on a film and you’ve got to show up with energy and be a bodyguard for the director in some way. I was faking my way through that stuff and that was exhausting. Mostly what I thought was just, ‘What time is it? When are we going to get off?’ I was sure it was done, but I didn’t know how I was going to keep my house running or travel freely or things like that if I stopped.”

His thoughts on women: Penn’s own feeling is that some feminists still want to be feminine, and some men are “getting feminized.” He thinks dating is getting more transactional for both men and women.

This is such a wild statement: He has experienced a fair number of relationships where “the first thing I see in the morning are eyes wondering what I’m going to do to make them happy that day. Rarely reciprocated.”

Who is this?? “On one of my marriages, the background noise of life was a ‘Housewives of Beverly Hills’ or another thing called ‘Love Island.’ Not even being in the room — I’m not saying this to be cute — I was dying. I felt my heart, my brain shrinking. It was an assault.”

He’s not in a serious relationship now: He feels “thrilled every day. I’m just free. If I’m going to be in a relationship, I’m still going to be free, or I’m not going to be in it, and I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again.”

His marriage to Madonna: “I had a freaking SWAT team come into my house.” Madonna told the police she was worried because there were guns in the house. “I said: ‘I’m not coming out. I’m going to finish my breakfast.’ The next thing I knew, windows were being broken all around the house and they came in.” Then, he added, “they had me in handcuffs.”

He never took a baseball bat to Madonna: He said he belatedly realized there were stories circulating that he had “trussed her up like a turkey. I didn’t know what ‘trussed up’ meant, first.” He said he was dating one woman who confronted him the morning after “a lovely night” when he was on the back porch smoking a cigarette. “She’s looking at me like I killed her dog,” he said, asking him “about this hitting Madonna in the head with a baseball bat. I didn’t know what the hell she was talking about. Now I think it’s fair to say that I’m not the biggest guy in the world. But if I hit Mike Tyson in the head with a baseball bat, he’s going to the hospital.”

He’s feelings on his ex-wives: “[Madonna is] someone I love…It turns out it’s a lot quicker to repair a friendship after divorce if there are not kids involved. It took Robin and I quite a while. There was a lot of drama… Much more important to repair it if there are kids involved, but no easy swing, right?”

[From The NY Times]

The ex-wife who watched Love Island and Real Housewife shows… that was his most recent marriage, right? He was briefly married to Leila George, who is Vincent D’Onfrio’s daughter, and they split very quickly in 2022. Was it Love Island-related??? LMAO. Imagine divorcing a beautiful young woman because she enjoys trashy reality shows. That other statement about his relationships – “the first thing I see in the morning are eyes wondering what I’m going to do to make them happy that day. Rarely reciprocated” – is so f–king wild, you guys. It reminds me of his whining after he and Robin Wright split, that she basically didn’t rearrange everything in her life to make him happy. It’s a special kind of self-centered to project that on women too, that they’re all wanting him to provide “happiness” for them while never reciprocating.

Photos courtesy of Avalon Red, Backgrid.

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19 Responses to “Sean Penn felt like he was ‘dying’ when married to a ‘Love Island’ & RHOBH fan”

  1. Looper says:

    He’s ick on the inside and outside.
    Let’s be thankful, ladies, that he’s seemingly keeping himself off the market for as long as possible, fingers crossed!

    • DK says:

      So full of ick!

      Also ick: “Whether he thinks he could play a gay character today: “No. It could not happen in a time like this. It’s a time of tremendous overreach. It’s a timid and artless policy toward the human imagination.”

      Since that quote is out of context, maybe I’m misunderstanding, but is he saying it was overreach for him, not-a-gay-man, to play a gay man in Milk? (If so, OK!)
      Or is he complaining that now there is greater recognition that characters with marginalized identities should be played by actors who share those identities, rather than well-established and connected white men who are not part of those marginalized communities? And that’s the “overreach” and “timid and artless policy” he is ranting about? (If so…ugh. Smacks of yet- another privileged and entitled white hetero dude complaining about all his perceived lost opportunities, and never considering the opportunities systematically withheld from others.)

      • Steph says:

        @dk yeah, I couldn’t figure it what he meant either and decided on the same two conclusions.

  2. Thais says:

    It’s so strange and disheartening, how people are willing to forget that this disgusting man is an abuser who for years defended dictators who tortured and killed thousands of political opponents, disgracing their countries, just because they hate the same politician. They are just like the people they say they hate.

  3. Chaine says:

    YUCK so full of himself. I’ll give him this—at least he’s not had a facelift and pumped full of fillers like Pitt, Cruise, etc. he looks like a normal dude his age.

  4. CatMum says:

    he is such a mixed bag! he does have some good points.

    however, I personally don’t see what’s wrong with relationships being more transactional. that just means that women aren’t forced to put up with men’s bs just to have food and a place to stay anymore. which is a good thing! I will certainly never get married again.

    he was also great in Milk. it’s one of the movies that I typically watch partway through and then turn off before it gets all sad at the end. (Boogie Nights is another one. as soon as the music changes from ’70s to ’80s, I’m out.)

    but I certainly wouldn’t want to live with him!

  5. tealily says:

    He’s so gross. Glad he’s so thrilled to be single. I wouldn’t think a guy who is thrilled to be single would marry three times, but sure.

  6. Justpassingby says:

    Is he wearing a toupee in the bottom pic?

    • IFoxi says:

      It looks like a deperate comb-over attempt to me. My FIL had something similar, but he executed it much better than ol Sean here. He also finally shaved it all off. Much better!

  7. lisa says:

    I married someone half my age and I cant believe we like different things!

    • CherHorowitz says:

      Ugh even if they were the same age, the moral/intellectual superiority people like to loudly profess when they don’t watch reality TV is so pathetic. Some of the most high IQ people I know watch the most trash. Sean, you don’t make yourself sound clever with that, just like an insecure snob.

      • BlueToile says:

        Yeah, Sean Penn has always thought he was the smartest person in every room. He needs to just stay single because he obviously loves himself so much there is nothing left over for a partner.

  8. Sara says:

    Remember when Sean Penn wasn’t around? Can we go back to that?

  9. Kristen from MA says:

    Every accusation is a confession.

  10. I know so many men who get salty when they do something “nice” and are not immediately praised and fawned over. If you do something “nice” with the expectation of getting something in return, IT’S NOT NICE IT’S MANIPULATIVE.

  11. Freddy says:

    Sorry kids, but he was asked questions and gave answers from HIS perspective. How do we call “ick” on someone saying how a marriage to a RH or Love Island fan made them feel? Personally, that would be a relationship killer for me too! LOL!! Oh and let’s get real–plenty of young women (and men) marry/date older men (yet rarely women) of means wondering what those older men can do for them….

  12. Kirsten says:

    Yikes does he make it clear why he’s not in a relationship right now. I know someone like this who thinks all of his conversations with women are terrible and boring — when he describes the conversations it’s because the women aren’t constantly making the conversation about him. Hard pass.

  13. GrnieWnie says:

    if all of your partners look at you with eyes that seem to be desperately asking you to make them happy…uhh, the problem might be YOUR eyes and what they see.

  14. Ciotog says:

    The guy cheated on Robin non-stop. Then whines about how he was just trying to make her happy?

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