What did Madonna ever see in Sean Penn?

I've always been attracted to Sean Penn... I mean, he looks like a chimney sweep in your picture, but he's looked good before. He was an especially handsome young man.

At least Madge had him when he was young, but what was Charlize thinking...

[quote]Could it be the 56 year old's prominent nose?

stupid. he wasn't 56 when they met.

R2 "a chimney sweep." Hahahahahaha!!!

Neither of them were in relationships at that time and both were riding the wave of success. Both were short and obnoxious! It was love! and then pugilism because they were both of immature psyche. We all saw it, said it wouldn't last and didn't. We all asked the question what do either of them see in the other.

There was a striking resemblance between a young Sean Penn and her father.

She's always been a professional beard, right?

I just assumed his genitalia was of a sizable proportion.

Sean Penn is to his gross ugly dead brother as River Phoenix is to his gross ugly unfortunately still slive brother.

He has elegantly wasted look.

He was a bit nuts. she was a bit nuts. They were both short. Made for a good temporary match.

Looks like beaker

Wasn't he once tipped to be our greatest living actor?

Nah, R13. He's just a 7 course ham dinner.

They go from pretty boy to homeless looking.

R13 Yes he was absolutely BRILLIANT in Fast Times. His portrayal was so true to life......he was better than Olivier.

He has always had the bad boy image

What did Sean Penn ever see in Madonna?

She was "like a virgin", r18?

She'd already forgotten what virginity looked like the day Nixon resigned.

He had BDF, had a great body, is still in pretty good shape, is passionate and liberal, and remember he won the Academy Award for 'Milk'. I like him.

Casting him as Harvey Milk was like casting Ricky Schroder as Malcolm X.

I red somewhere that he is very good in bed and that Madonna complained to a friend at the time she was dating Warren Beatty, that she missed Sean because sex was better with him.

R23 = Sean Penn

Around the time of At Close Range, he was sex on a stick. Nowadays, more like shit on a stick.

They married when he was 25 (she was 27) and divorced when he was 29 (she was 31). I thought that Sean Penn was hot/sexy in a bad-boy kind of way. So I saw the appeal. Then. Don't think he's too attractive now. They were both big stars at the time. Their first joint project SHANGHAI SURPRISE received a lot of press, during all production of the film and immediately after its released when it got trashed by the critics and bombed at the box office. It was the GIGLI of its day and became a punchline. It left a bad taste in people's mouths, and I believe that's why their pairing seems odd now.

Incidentally, for the longest time I thought that Sean was Arthur Penn's son. Had no idea about Chris, so he never mattered in the equation.

What did Sean Penn see in Madonna?

They were both short , famous, given to explosive anger, thought they were cool, etc actually a lot in common.

R28 At the time, Madonna was the "It girl" of the pop music world. When they married, she had just released LIKE A VIRGIN the previous year, and during their marriage she released TRUE BLUE and LIKE A PRAYER, which further elevated her status. She was also considered sexy. Men wanted to bang her -- and apparently young women/girls wanted to be her, since they appropriated her style.

White trash tends to attract white trash.

Sean Penn and Madonna are both nasty. What did Guy Ritchie ever see in Madonna?

He was a good mix of pretty boy with tough hood. He had a boxers face. He was a big star and didn't have much class, like Madonna, but they both had a lot of moxie. Also we all assume, he's got a hot cock and liked to fuck.

Were Madonna and Penn constantly in the tabloids during their marriage? I imagine there were many heated arguments, even physical confrontations.

R34 Penn would attack paps that tried to take a picture of them. There were helicopters at their wedding trying to get shots of them, I think Penn got out a gun to shoot at them. That's what got the most tabloid attention. The more he went on the attack the more the tabloids wanted a picture of him on the attack. I don't recall a lot of fights between them being reported during their marriage. At the end there was a report of him tying her to a chair at gun point. She now denies this, but it was widely reported at the time.

Spicoli years

boys 1981

Guy Ritchie saw Madonna's money, lots of it, and he collected in the million$ when they divorced.

Madonna of course saw Sean's massive sizemeat!

God,Tom Cruise was UGLY then ! Sean was hot,and I did like him as an actor,but his swollen ego turned me off of him and I havent watyched him in anything since that god awful movie Mystic River. Talk about chewing up the scenery ! When Bad Boys came out I used to fantasize about being locked in a cell with him .

Can you imagine if they had kids...

Well the kid with Ritchie is a grungy little chav so yes I could imagine a kid with Penn, as well. At least wouldn't be as dumb as the Ritchie boy seems.

I remember when Madonna's daughter and Michael Jacksons' son were born within months of each other. Many people were speculating (or hoping) that, when they grew up, they would start dating or something. I don't recall Prince's son getting as much coverage, but he was born during that four-month window, too, but sadly he died shortly after birth.

.[quote]There were helicopters at their wedding trying to get shots of them, I think Penn got out a gun to shoot at them.

He didn't get in trouble for aiming the gun at someone(s)?

OPEEEEEE! The timing of the appearance of your thread is too bizarre! In that I was just thinking this morning about their initially getting together. (I know, I'm weird.)

Anyway, the first I'd heard about their dating was in an article in "People" magazine. (I can still recall the accompanying black/white photos.) Upon reading the article, my immediate thought was, "Ahh, in addition to being a singer, she's also an opportunist." (Sean had an already hot film career, fresh off of "Taps" and "Fast Times at Ridgemont High"; he had industry visibility and useful connections; he had a famous movie-director father; and he was/is "Hollywood Royalty.")

Actually, Sean's father is Leo Penn, a third-rate tv director (think Matlock). Arthur Penn is the movie director (Bonnie and Clyde, etc.) you're thinking of. Sean Penn and Arthur Penn are not related, to my knowledge.

Years ago I saw Sean Penn and Kevin Bacon in a play on Broadway.. Penn had a huge amount of sex appeal; I am surprised Penn is under appreciated here.

R46 I think because the posters (many of whom I believe are the younger set) are thinking of how he is and what he looks like NOW. But if this were DL circa 1987, most people would be saying how sexy he is. Many people definitely thought that at the time. DL is just rewriting history, as usual...

I'm old enough to remember Sean Penn when he started out and as he emerged as a movie star and um, no I cannot ever recall any publicity or public reaction alluding to his "sex appeal." Ever.

Big muscles, big dick, big macho attitude.

R45, are you aware of how much Leo Penn's career suffered as a result of blacklisting? That's why Sean was so pissed at the Oscar recognition given to Elia Kazan, a chief collaborator. Try being less obnoxious.

They were truly a match made in hell. She loves attention and publicity, craves it, can't do without it. And he hates it. Later when asked about their relationship he said something to the effect that it was a mistake to think that a few great dates would be enough to warrant marriage.

I don't think the "Penn tying up Madonna and beating her up" is mere hearsay. She denied it recently (when she was getting chummy with Penn again), but at the time she refused to file charges. I'm kind of disappointed in her. This would help out many battered women, if she talked about it and didn't deny it.

R51 Bullshit. He's as much a media whore as she is. He's always banging on about his philanthropic shit he can't wait to squeal to the media about. He saves AIDS orphans in Haiti you know. He even lives there sometimes as Hollywood is just too much for him!

He's an actor with a ginormous ego. They crave attention and can't live without it.

She denied it to help Sean with his defamation case against Lee Daniels, R52

[quote]What did Madonna ever see in Sean Penn?

His big cock?

Madonna is known to be a size queen.

Years ago, there were stories of her riding around Manhattan in a limo cruising well known male prostitute areas of the city. The guys on the corners were gay, but all she wanted to do was suck their cocks, they didn't have to fuck that whore.

Madonna mostly preferred young Puerto Rican guys with big cocks. Probably still does. Madonna has always been cheap and vile, no surprises there.

I was a kid, maybe 10 or so, when he co-starred with Ally Sheedy in a movie called BAD BOYS. He was really magnificent in it and sexy as hell.

He has that glare in his eyes - the same as a poodle looking at a mophead and saying " I'm going to fuck the shit out of that rabbit!"

"He's an actor with a ginormous ego. They crave attention and can't live without it."

He's not "as much a media whore as she is." NOBODY is as much a media whore as Madonna. Penn has never sought out publicity like the attention whore Madonna. You sound like a real idiot.

R37, Tom Cruise pre chin implant!

Sean Penn always had beady eyes and a mouth like an asshole even as a young man. Now he looks like a raddled old sleaze. Never got the appeal.

I do not believe the Madonna sucking tale. She has a lot more self-control than that.

R55, I remember those stories. One of her friends at the time said that Madonna would purposely look to pickup up teenaged latino men because nobody would believe them if they ever said how she pursued them.

She saw a movie career. She said she got with Guy Ritchie because she thought he'd put her in one of his films. She's a user, always has been.

Jennifer Lopez was once quoted as saying that of all of her leading men, Sean Penn was the best kisser.

So, perhaps he does have a tender side?

Madonna has had plenty of secret dick on the side. Years after it happened, a sheepish Henry Rollings ended up confirming that he was her booty call boy toy for a few months back around the time she put out that Sex book. She had him on call for a bang when needed, he was the one who wanted it kept private too since he was getting famous at the time and it would've killed his image.

I found him incredibly sexy when he was young,probably because my 1st real boyfriend had a mouth exactly like his,but I digress. I always enjoyed his movies very much,but Mystic River was indeed a piece of shit and his bullshit humanitarian posturing ala Angelina Jolie completely turned me of him as a person. Not to say I wouldnt watch him in a movie again,but I do wish he'd stop being such an asshole.

R55 NO ONE will believe Madonna drove around looking for dicks to suck EVER. She is a "Do Me" type, probably kicked em out as the afterglow fades.

Sean Penn and madonna are both gay. Don't let reality affect your analysis.

R67 is the "Everybody on planet earth is gay " troll !

In Bronson Pinchot's memoir he wrote that when Risky Business was filming, Sean visited Tom Cruise and they shared a hotel room. He all but came right out and said that they were fucking.

He repulsed me. He has never been in one single role that didn't bug the living shit out of me. A terrible combo of shallow, arrogant and unintelligent. Cannot stand the sight of him. How he is a movie star is beyond me.

Uh, he's a great actor, r70. Nobody said he was a great individual.

Ironically, Madonna still hangs around him.

What did Robin Wright see in him? She was married to him for over 20 years and there were stories of him abusing her and she wouldn't leave. Robin Wright was so beautiful and talented when she married Penn and she didn't act for years. Now that she's free of him, she's really blossomed as an actor.

Robin Wright -- she gave her best years away to Penn. Madonna still wanted Penn back but Robin had him.

I bet he throws a mean (and awesome) fuck.

R68, 95% of male actors r gay. 3%of males overall r gay. I can't imagine a straight male choosing acting as a career.

In OP's photo he looks like a homeless person.

Or at least someone who doesn't own a comb.

I was obsessed with Sean Penn as a kid. I think I watched At Close Range like 50 times on video. He was just smoldering -a downtrodden, beefy anti-hero who somehow made blond highlights look butch.

Nope nope nopity nope

Madonna uses people and then moves on -- quickly when they fail to help her career -- especially when it came to movies. Examples include; Sean Penn post-Shanghai Surprise; Warren Beatty post-Dick Tracy; Rupert Everett post- Next Best Thing; Guy Ritchie post-Swept Away. She is a very public example of a sociopathic user. How many more examples are needed to understand that Madonna is a ratchet person?

What did Sean Penn SEE in Madonna?

I think Madonna is still in love with him. He’s one of the few men who stood up to her and he didn’t take her crap. That’s why she’s so enamored of him. He slapped her around, which she egged on. She really delighted in it.

Most likely he's a big dicked fuck machine. Face it, even now he's got a kickin' body.

His face is morphing into George C. Scott.

What's wrong with Robin Wright? He treated her like garbage, beat her up for twenty years, gave her who knows what diseases from all his side pieces (remember when bailed Eve out of jail at 4am?) and finally she gets free of him and hooks up with Ben Foster who is basically the uglier, less talented, Scientology version of Penn from when they first met...What happened to her? Why does her idea of a relationship include an abusive, arrogant, melodramatic prick who castigates her for sport?

Behold 24 (!) year old "model" Hopper Penn...

R76 where did you get those statistics?

Robin has bounced back nicely from both Penn and Foster, because she just got married to a 29 year old French boy toy who's hotter than both of them. She looks ecstatic in all the pictures with him. Get it gurl!

Penn was great as Milk- obviously he has lived hard- he was sexy when he was younger.

One of my favorite movies with Sean Penn was from 1984, 'Racing with the Moon' starring himself asking the young Nicholas Cage and Elizabeth McGovern. It was release to some critical acclaim. A beautiful period piece about small town boys, about to go off to WWII.

Actresses: never change your name! It's as big a jinx as winning the Best Actress Oscar when you are under 45.

Robin Wright Penn, Courteney Cox Arquette, Rosanne Arnold, Joanne Whalley Kilmer: all divorced!!

Exception: Jada Pinkett Smith.

See below.

He was charming when he was younger. Handsome, but as he aged the bird-face features took over. Not sure what he saw in her.

Didn't Sean Penn start fucking Madonna again a couple of years back? Can anyone just say yuck?

Off topic, but what the heck was the deal with Charlize and Sean?

And didn't ScarJo date him briefly as well?

If it's lesbian, it dates Penn.

[quote]Not sure what he saw in her.

Seriously? Are you that gay? At the time, Madonna was considered sexy.' Many straight men wanted to bone her.

He has a strong masculine energy.

He was also dating Vincent D'Onofrio's daughter. R94

I met him twice in the early 90's and he was charming and very sexy in person.

Madonna's father. A young Sean Penn looking a bit like him, it's true.

Sean was young and hot and he was younger and hotter

Wow, Madonna's father was a good-looking guy.