Madonna & Sean Penn | Splits

Katie, it feels like Madonna, one of the biggest pop stars, the 80s, 90s, really just all of pop music, is back in the headlines once again. She's got the Celebration Tour, she's got documentary projects. She's made comments reflecting on past marriages, relationships. All this stuff is coming up again. Madonna just somehow finds a way to remind everyone that she's lived about five or six lifetimes in one. And whenever people talk about Madonna's relationships, there's really one name that always comes up, and that's Sean Penn. They were both young. They were very, very famous. They were beautiful and they were volatile. This four year marriage became one of the defining celebrity romances of the 80s. It was equal parts fairytale. There was tabloid circus and it was really a cautionary tale. Helicopters, paparazzi chases. We're going to get into all of it and find out how one of Hollywood's most explosive marriages became one of the strangest second acts. I'm Derek Kaufman. I'm Katie Hayes. And this is Splits, Madonna and Sean Penn. Right. Well, so every week we should say we talk about what Hollywood divorce we'd like to discuss. Yeah. And sometimes they're like back in the news again. This is one of those examples because Madonna has been on a press tour for what's the name of the album again? Celebrate Confessions 2. She always has. She's used all the good names. So now we have part two of Confessions because she's got a lot of things to confess. And she did this song called Bizarre that directly references her tumultuous relationship with Sean Penn, which was really more than 40 years ago when they first met. 40 years ago. She's still singing about this guy. So we said, OK, obviously this week has to be Madonna, Sean Penn. We start looking into it. Boy, oh boy, this is hot. This is volatile. This was everything you could imagine in a pop star, movie star relationship. And young, hot, young, hot Hollywood and New York. Frankly, she was big in the music scene everywhere. She was already becoming a global icon. He was a rising superstar in the in the movie scene. Let's set the stage a little bit. So 1984, Madonna and other pop stars. It's just a great time in pop music. You got Michael Jackson on the rise. Madonna is just becoming one of the biggest female pop stars in the world. She's got Holiday, Borderline, Lucky Star, Like A Virgin. She is a cultural lightning rod. Huge. Yeah, absolutely huge. And Sean Penn, no slouch. I mean, this is he's becoming one of Hollywood's most promising young stars. You have kind of the Brat Packers, but he's considered a more serious sort of rising talent in this world. He knows all those people like the Rob Lowe's and, you know, the Emilio Estevez and all those sort of Brat Pack scene. But he's in Fast Times at Ridgemont High, where he's Spicoli, an absolutely iconic role. He's in a movie called Bad Boys and the Falcon and the Snowman. And he's emerging as this sort of very serious force in Hollywood, young Hollywood, very serious, but also bad boy. And yeah, that was bad girl. Yeah, I mean, she was breaking all so she was breaking all sorts of boundaries. Right. For women, she was sexual. She was doing, you know, like a virgin. They were both crossing all of these things in pop culture that you hadn't seen so far. Right. Like a Virgin is about but but play. What is like a I thought it was just like a virgin, like normal, normal. Oh, I thought it was like that other play feels like a virgin. Because I don't I don't know. Maybe I'm wrong about that. We're going to need to relisten to like a virgin. We should check it out. Somebody's going to need to somebody's going to need to write in and tell us. But OK, so they're massive stars. They're massive stars. They're huge. She's huge in music. He's huge in movies. And they come together. They meet in early nineteen eighty five. They were filming Madonna's music video. The best song of hers of all time, in my mind, is material material. They're filming the the iconic music video for that MTV is at its absolute peak. So and they film and it is immediate chemistry. Yes. Now we should hot and heavy, super hot. But we should say Sean Penn was very private. Yes. Madonna was not private at all. And she was really pretty much the most photographed woman on earth. She's built a whole brand on openness. Right. I mean, she's open about her sexuality. She's open about her relationships. She is out there, out front. And he's a guy who, even though he's a Hollywood star, hates the paparazzi, has always sort of had a problem with, you know, giving up his privacy. He thinks I'm a serious actor. That is my profession. You can see me on the big screen, but you don't need to fly helicopters over and take pictures of me. Get out, get out, get out, get the **** out. Big sort of rift already. Yes. Between their two temperaments. Now, she plays along and she also wants some of her privacy while she's with him. But that is already sort of something that could never really work. The two the the way the two handle the media. Right. But the attraction was so powerful that they just had this insane whirlwind romance. Right. And so Sean Penn starts going to he's a frequent presence at her on her tours at her video shoots. She has described him as incredibly funny, passionate, deeply loyal. They both admire their ambition. They both admire each other's work ethic. Madonna is a bigger star at this point. Yeah, no doubt about it. They very quickly get married. Now, we should say this is 1985. Madonna's only 27. Sean Penn is only 25. They are baby. They're babies. They're babies. And they're just, you know, rising into their, you know, superstardom. So they're still very committed to their work. But they have this big wedding in Malibu. Right. And they're already both famous. Madonna, as you said, is already this kind of global icon ascending up there with the Michael Jacksons of the world. And it obviously attracts a lot of attention. They're they're a big Hollywood couple. So there were helicopters flying around Malibu. Not to mention anyone who's who in the 80s was at this wedding. Yes, Cher. We had Carrie Fisher. We had Andy Warhol was there. Tom Cruise was there. It's Diane Keaton. It's everybody that's big in the 80s is there. They're getting married on this cliff. Cliff in Malibu in the wide open space. So the helicopters come, of course, the helicopter helicopters come in. Yes. And Malibu, he grew up in this sort of scene with Charlie Sheen. You ever seen that documentary? He knew Charlie. He knew that he was part of the Hollywood scene. But Malibu is like kind of forced country. You have to describe for people. It's not Hollywood. No, Malibu is off the cliffs of the Pacific Ocean. It could be more remote and feel a little bit more private. This was anything but. And certainly back in the 80s, it was much more private than it is now. I mean, they really described it as it was a horse town and people got a lot of privacy there. So this is kind of the wedding is what people describe as kind of a foreshadowing of their relationship, because these helicopters show up. They're loud. You can barely they can barely hear their vows. And Sean Penn apparently loses his mind. Reportedly was screaming obscenities at the helicopters in the sky. At one point, allegedly wrote F.U. in the sand so that they could read it above. And, you know, they have this. Apparently it was a very romantic wedding. They added all these playful moments where they got on the balcony and he goes up under Madonna's big 80s dress and takes off her garter. But it was definitely overshadowed by these insane helicopters. And it was kind of just the start of a little taste of what was to come. Yes. Sean's breakdown over all the paparazzi stuff and just the volatility of the relationship. Yeah, he's never been a calm guy. And even in his, you know, now he's in his, I guess, 60s or at least late 50s, early 60s. He's volcanic. His temper is something that he is very well known for, and he is always in a confrontational or hostile posture with the paparazzi. And when you're with the most one of the most famous people in the world, you're going to attract that attention. And it's just oil and water. He can't figure out how to make that work. But there is a honeymoon period because there's so the chemistry is so hot, right? This is a hot young actor and the hottest young pop star. And so they start buying homes. They attempt to sort of balance these two massive careers. And she's writing songs about Sean Penn. He's inspiring her musically. She appears in Madonna or sorry, Sean appears in Madonna's True Blue era and stars opposite her in a movie called Shanghai Surprise. This is 1986. Blow me 10 cents, man. Will you? I'm dry as a bone. Absolutely not. I do not approve of drinking. Look at me. I'm shaking. I can't even go to you like this. You're wasting your time, Mr. Wasey. What about rice? Rice? You don't have anything against rice, do you? I haven't eaten in three days. Give my vigil. Rice, wine. Look at that study is a brain surgeon. So we got to talk a little bit. I wanted to pause here. Sean Penn's an incredible actor. He is decorated. We'll go into he's won Academy Awards. I believe he's a three time Academy Award winner for best actor, most recently for best supporting actor in one battle after another. Right. He's incredible. He jumps off the screen. He's been in milk and so forth. It's not her strong suit. Oh, I beg to differ. She has had some clunkers, but suddenly, Susan, delightful. She really knocked it out of the park. Insane. The music's always on point. Don't even get me started on maybe the best film of all time. Dick Tracy. Oh, Dick Tracy. She's very good. I do forget about that. Actually, kind of a catalyst, which we'll get into in a little bit. The Warren Beatty era. Yeah. But obviously, Sean Penn's the actor. And so they both take on this movie, Shanghai Surprise. And they set out to really be Richard Burton and Liz Taylor. They really did. That was going to happen. They thought this is our Cleopatra, Shanghai Surprise. And it is a surprising. This movie is a clunker. It was it was critically panned. It was a box office bummer. It was just bad, all everything bad. And then they didn't do well on set. The crew hated them. Yes. They because because they're young and immature and paparazzi were constantly swarming them. So what they did is they kind of isolated themselves. Right. So there were lots of stories about the crew being in all these and all this onset in really uncomfortable weather climates and doing all these things while Sean Penn and Madonna are just holed up in their trailer. And so they did not create a lot of making love. She likes making love. She does. She's into it and making love. But it didn't that didn't win them any favors with the crew. So they walk away from this movie and it's an epic disaster all around. And now they're starting to really fight with each other. The reviews are brutal. I mean, I just want to linger here. It's it's it's a miserable production. It's a miserable movie. It's not fun. You know, it's not like a fun flop where you can revisit it and it at least looks like they were having a good time. Like like a Geely. Like a Geely. Right. Like that movie was terrible, but it looked like they were enjoying themselves. They enjoyed it and they sort of like emerged from it. OK, this one is it's it's it's a massive flop. And I think it strains it. Yeah, because they both also have massive egos, because everything they had really done up to this point was really successful. Like you said, she's in her true blue era, which was a massive hit. Another massive hit for her album. She's at the peak of her career. He's really kind of, you know, he had his big hits and he's at the not quite the peak yet, but he's up. But he's emerging. And then this is a huge blow to both their egos. And they're both stubborn. They're both competitive. They're both working constantly. And this this made them take a hit. Right. And so if this had been successful, we could live in a parallel universe where they're just a massive couple like Beyonce and Jay-Z. It's like dominating Hollywood for decades upon decades. But I think it's her limited acting ability that really sort of just like ruined that potential. She's a wonderful musical artist. I've always thought she struggled. It is a repeat pattern. Her next husband, Guy Ritchie, which obviously we can. What was that movie where she drifted away, swept away? Oh, man, it's so bad. Responsible for some clunkers, but also some really delightful films. She so badly wants to be a triple threat. And she's a one threat. No, she's a she's an entertainer. A double threat. What's her second? She dance. Oh, you think she can move? So, yeah, just on the in the World Cup. Come on. Oh, yeah. She's still got it. I'll give her a double threat. So back to the downfall. Yeah. So so so now this is straining the relationship. Really Shanghai Express is a big, big sort of turning point. And then there's sort of sort of start to be stories about jealousy, explosive fights, long separations where they're working on different parts of their career. Friends are suggesting that they spent surprisingly little time together. And one thing they needed was that chemistry was all of the like passion between them. And if there's separation, it leads to outbursts, his temper and so forth. Things are starting to fray a little bit. Penn is accumulating legal problems involving altercations with photographers. He's still got a problem with all the press attention. Yes. And his anger is like he's becoming as famous as his acting. He's a bad boy for attacking photogs who are constantly out to get pictures of Madonna. The two of them is a couple. But really, it was Madonna that brought a lot of it. And that's jealousy somewhat. And so that was the big thing was that Sean Penn was constantly, allegedly jealous of Madonna and not only for her fame, but also huge issues with any ex-boyfriends she had that she stayed friends with anyone he even anyone that was even good enough to be a potential lover for Madonna. He reportedly was jealous of. Yeah. Some of this seems like insecurity, immaturity, all of it at once. Remember, they are still very young and there's start to be reports of physical altercations throughout throughout the marriage. And then we have to get into it. So so his career, while he is considered a wonderful actor and one of the likes of rising stars to maybe win awards in the future, kind of like Robert Downey Jr., the bad boy stuff is starting to cloud out some of the like talent a little bit. And it really comes to a head with this infamous incident in late December 1988 at the couple's Malibu home. And this is a nasty. And and we should even get to there was there was a big fight before it where we started to see 1986. Now, we should say Madonna has denied all allegations of any sort of physical abuse from Sean Penn. She's basically recanted all of this. Yes. But there was another there was a book that came out, Madonna Unauthorized, where this the author interviewed friends, colleagues, anyone in their circle. And so there were a lot of stories, mainly one being 1986. There was a Manhattan nightclub incident at the pyramid. Apparently, Sean got super jealous when he saw Madonna hug somebody. He shoved her against the wall. They continued shouting in the street. And that was a huge fight, which eventually then led. We get into Christmas. Yes, 1988. Now, is it 88? It's 88. Malibu. Yes. So a couple a couple of things here. Madonna was hanging out with Sandra Bernhardt more and more. And they were great friends. Very getting very angry about this because they would go out. They'd be coy. They do like kissy kissy. And Sean was furious about this. Sandra Bernhardt was very hot at the time. There's a hot lesbian energy to Sandra Bernhardt, just to put that out there. And Madonna is all over the map. Also, everything. Yes. And so also, allegedly, Madonna had promised Sean Penn that they would start a family around Christmas 1989. Well, she really wanted the role in Dick Tracy's movie in Warren Beatty's movie, Dick Tracy. Do you remember her character name? No. This is why you lost Jeopardy. This is why you came in third. I'm sorry. This is breathless Mahoney. Breathless Mahoney wanted. She went apparently behind Sean Penn's back, campaigned herself to Warren Beatty, landed the role and then said, sorry, we have to postpone starting a family because I've got to go sing sooner or later, you're going to be mine. So Warren Beatty, the greatest movie of all time. Sooner or later, you're going to be. Baby, it's time that you faced it. I always get my. Can I tell you one quick story about Dick Tracy? That is really funny to me. He still owns the rights to it, Warren Beatty. And because the rights will revert to the old comic book people, unless he uses the rights, he dresses up like Dick Tracy in random interviews and he portrays himself as Dick Tracy so that he can say he has an active project. And you see him, old man in that yellow suit with the hat. There's many, many videos of him just keeping the rights to Dick Tracy alive. This is a hilarious fun fact I was unaware of. Well, I mean, this is really this is kind of the catalyst here. So apparently this was all right before Christmas. They spent Christmas Eve separately, according to this book. Madonna spent Christmas Eve with Sandra Bernhardt and Sean Penn spent it with a stripper. It's a real trigger for Sean. He went to the arms of a happy, happy Christmas. So at this point, I guess he moves out, moves back in with his parents because remember, he's only 25, allegedly started making abusive calls. And then that's when this massive fight we've heard about in Malibu happens a few days later. There's a version of this where he allegedly tied Madonna to a chair and sort of held her hostage. It was physically sort of a violent, explosive fight at their Malibu residence. He she did go to the sheriff's department, made some of these allegations. Yeah, so that's the thing. So according to these stories you hear, she was able to escape, jumped into her Thunderbird and took off, went to the police. Now there is a she went to the Malibu Malibu Sheriff's Station. There is there was a police report filed. Right. We do know that for sure. Yeah, at the time she there was a report. But the criminal charges never sort of materialized. He was never charged with anything. And as a matter of fact, she has been since that event. Years later, she submitted a sworn declaration saying that Sean never struck her, never tied her up, never physically assaulted her, as she described in those as as was described in longstanding accounts. Many of these were tabloid accounts, but there was some involvement of law enforcement at the time. And so now it's clear they put it behind them. And she sort of changed that narrative. But this really was the nail in the coffin for the relationship. It really was. So it was about a week after that incident that she filed. Madonna filed for divorce. Hard to come back from that. Yeah. On grounds of irreconcilable differences. But that same day, she also met with the deputy district attorney and said she wanted to withhold her complaint. So there was a complaint. We don't know what was in it. She did withdraw. She wanted to turn the page, though. It sounds like for everyone involved and her love for Sean and his his career was on the rise, hers was on the rise. This would have derailed it potentially in a in a catastrophic way for both of them, potentially. Right. And so it sounds like she withdrew, turned the page and has changed this narrative over time. And, you know, a lot of people say like this is why domestic violence, you know, perpetuates in society. But if she felt that she wanted to move on and not have this define her, it is her choice to sort of withdraw. Right, exactly. But you do have to wonder, even though she has denied it, just you, I just we talk about this all the time. I say, how do you just want to see what's in that incident report that she filed in Malibu? Right. That was all the answers. But she's changed the whole story. And it really was just between the two of them in this house and all these allegations of chair tying and escaping into her car. And so the Thunderbird and so forth. She says the physical altercation didn't happen. It didn't happen that way. So now they break up. This is the end of like a crazy relationship. The aftermath, because this happened in 1989, is like a majority of their careers went on and went on with tremendous success. Madonna redefines pop music in the 90s. All of her 90s era stuff is past Sean Penn. They're done in 1989. She then goes on in her personal life to a litany of very public relationship with very famous people. We've got Warren Beatty from the Dick Tracy era. We've got Dennis Rodman with the colorful hair. That was a hot one. Very hot. I mean, this is a guy who's six foot eight, yoked. You've got Carlos Leone, her trainer. She had a baby with Guy Ritchie. She starts a family with in 2000. This is even a decade past a past. This is when she becomes British. Her accent changes. Her accent completely changed. She's just British Madonna at that point. She moved to England and then same thing happened to them. They did a movie. He drew. He's a, you know, obviously world. He's massive. Yeah, lock, stock, two smoking barrels, the whole thing. Did created essentially the worst movie ever done on planet Earth, swept away with Madonna. And that was that was some of her some of her film projects. It's a spotty history. I do like Suddenly Susan, too. Yes. Suddenly Susan desperately secretly secretly. Yeah. Suddenly Susan is a nice show. That's Brooke Shields. That's Brooke Shields show. So she look, she has a huge family now. She adopted several children. She has Lourdes with Carlos Leone, right? So she is now a mother. And things are pretty good. I mean, she's the queen of pop. There's no one bigger than Madonna from about mid 1980s to about 2000. She has Ray of Light in the late 90s, which is another huge song. She is in the dance music. I don't have to give you Madonna's resume. Sean Penn becomes one of the signature actors of his generation. There's no doubt about it. He has two children with Robin Wright, who is Princess Bride. That's Buttercup. So he has a long marriage to her in the 90s. They have two children. Also a little volatile. They a little volatile. They filed and not unfiled, but they filed and then withdrew divorce. That's another episode. And then filed and then would withdraw. And then finally, eventually they I think they even at one point got divorced and then got remarried. There was a lot. That was another episode. But it was definitely up and down. They did have a family together, though. They they went on both having big careers. Oh, massive careers. But he becomes one of the most decorated actors. He is in films like Dead Man Walking, Mystic River, Milk. He wins three Academy Awards. There are very few people that have three Academy Awards. He's got best actor for Mystic River and Milk, and he's got the supporting actor for recently One Battle After Another. He has changed his whole persona. So he was this volcanic bad boy during the time with Madonna. Now, what you think of with Sean Penn, other than the Oscars, is his humanitarian work. And he's really worked hard to, you know, he goes to do relief work in Haiti. There's pictures of him after the 2010 earthquake relief work in New Orleans after Hurricane Katrina. He filmed a documentary about the about Ukraine, where he goes over and hangs out with President Zelensky. He has one hiccup where he hung out with El Chapo while El Chapo was on the run. Right. He has called that a failure. This was a wild episode where he met up with an actress named Kate. Kate Del Castillo set up a meeting with literal fugitive drug dealer El Chapo. They published a Rolling Stone article where El Chapo gets to review it before publication. People go crazy. And it's a really a sort of embarrassing episode for Sean Penn, who had done mostly humanitarian stuff. And now he's with a drug dealer, you know, notoriously sort of vicious guy. Puts that behind him, though. And I think you do mostly think of him as doing good humanitarian work. He's a very serious guy. I you know, it's funny. I don't think he's totally very leathery, too. He's so leathery. I don't think he's worn sunscreen his entire life. I think he's still Hollywood's bad boy a little bit. Oh, OK. Because you still see him. He just never he's never given in to the you know, whatever he's supposed to say. He's still very much Sean Penn. We see him smoking cigarettes inside the Academy Awards last year. You're like, there is no smoking in here. There's no smoking allowed, sir. And he just doesn't. He does what he wants. Like Dejah Pellicotta. Yeah, but not him. I don't think he cares about his public persona. Like he is Sean Penn. He doesn't wear sunscreen. He smokes cigarettes. He just did a documentary when he did the Charlie Sheen documentary. Documentary. And he came and gave testimony. He smoked the whole way through that. He just is a guy who is who he is, who has the texture of an old baseball. He does. But he also bangs Hollywood's hottest women. Do not forget that he dated Shirley's Throne after Robin. Oh, yeah. And I mean, he he's been through a couple other really hot girlfriends. I mean, Robin, right. One of the most desirable people on earth. Right. Princess Buttercup and Charlize Theron just played Calypso in one of the most beautiful women. So Sean Penn, there is this mystique about him. And I think even though now he does all this humanitarian work and he's obviously mellowed out a little, he has this. Even though he's an old bad boy now, there's this edge that is very intriguing. There's an aging bad boy. And he's buddies with Charlie Sheen. He's seen some stuff. He has seen everything you have seen and more. Exactly what Like A Virgin is about. I guarantee you. Absolutely. I guarantee you. So where does this all end? So they were very young. It was very volatile. Madonna and Sean Penn. She's been on this tour talking about her old relationships. She releases this song where she references that Malibu episode, I believe, or references their relationship. She she references. Yeah, she talks about that, basically saying how much she loved him. She talks about his eyes, the carriad. And then she does say one of the lyrics is roll out the red carpet for me. But I guess you won't share it. Yeah, that's a slam. Jealousy. The jealousy side. But I think at the end of the day, and Madonna Madonna even said this after their marriage, when someone asked her who the love of her life was, she said, Sean, Sean, it's wild. And then that's her first true love when they're young. They're in their 20s. They're idealistic. Their careers are rising. It's very different than when she gets with Guy Ritchie and he gets with Robin Wright when they're already established superstars. And Sean Penn has said she's someone I love. Yeah, she's a good friend. He's been less gushing. He's not as gushy. But they did go on to have this kind of they've always had a mutual respect. And I think they did keep it. It was it was a little shocking to me, this confessions, too, that Madonna was still doing a song about what she does, though. She's always in promotional mode. Yeah, that could be pushing her relevance well into her 60s. And it's hard. A lot of people who are in younger generations call her cringe. They say she's grasping at relevance too much. I love Madonna. Madonna's always been Madonna. And Madonna said in her last concert, the only thing she's done wrong is still sticking around. That's it. She's right. She's going nowhere. You know, she is. And I love it. You know, let her. I want her to dance and sing until in her little body tight body outfits until she's I notice you said dance and sing. And you didn't say act because I think she should hang up her acting. No, I will. I would definitely watch it. Desperately seeking. Would you like Sean Penn to get into singing and dancing more and less acting? It's an interesting question. They do it for both of them. And you know what? This is one relationship. I do feel like it was so toxic. But if they ever came back together, I wouldn't be mad about it. I wouldn't be mad at all. They're a combined triple threat. He can act and she can sing and dance. All right. That'll do it for us today. We'll see you next time on Splits.