Following Sean's on screen kiss with fellow male actor James Franco in the film Milk, he sent a text message to ex-wife Madonna with the message, "just popped my cherry kissing a guy. I thought of you. I don't know why.' Sean has another gay scene in the film with Mark Martinez.
In 1996, 2002 and 2004, Sean was nominated for SAG Awards. All 3 years, he was nominated for "Outstanding Performance by a Male Actor in a Leading Role. In 2004, he was also nominated for "Outstanding Performance by a Cast in a Motion Picture". In 1996 he was nominated for Dead Man Walking. In 2002, he was nominated for I Am Sam. In 2004, he was nominated for Mystic River.
Citing irreconcilable differences, Sean and wife Robin Wright Penn, announced in December 2007 that their 11-year-old marriage was over, and filed for divorce. The pair sought joint custody of their two children, son Hopper Jack, and daughter Dylan Frances. Five months later, they reconciled and withdrew their petition.
His performance as Jeff Spicoli in the movie Fast Times at Ridgemont High is ranked #9 on Premiere Magazine's 100 Greatest Movie Characters of All Time.
He was paid $5,000,000 for the movie I Am Sam.
His brother Chris died on January 24, 2006.
There is a popular indie-band in The Netherlands that is called Seanpenn.
He was briefly engaged to actress/photographer Pamela Springsteen. She is the sister of Bruce Springsteen. Sean and Pamela were both cast in the movie Fast Times at Ridgemont High.
He has said that Malcolm McDowell is the best actor with whom he's worked with.
He is the only actor to ever receive a Best Actor nomination for a Woody Allen film besides Allen himself.
His middle name is Justin.
His brother Michael Penn is a musician.
His parents are Leo Penn and Eileen Ryan.
His brother Chris is also a actor.
In October 1997, he was ranked #76 in Empire Magazine's Top 100 Movie Stars of All Time.
Sean was listed as one of the twelve "Promising New Actors of 1984" in John Willis' Screen World, Vol. 36.
Sean appeared with his brother, Chris Penn in the movie At Close Range. Also in the movie their mother, Eileen Ryan, played their grandmother.
In November 1993, he and his wife lost their home in Malibu because of a fire.
He and Robin Wright Penn lived together from 1991 until they got married in 1996. They had two children before they got married.
He served 32 days in jail in 1987 for hitting an extra.
He was married to Madonna from August 16, 1985 to January 10, 1989.
He is married to Robin Wright Penn. They have been married for 9 years. The have two chilren together.
Won the Academy Award for Best Actor in 2003 for his performance in the movie Mystic River.
Sean: I had a house burn down once, and everything in life burned, except my family, and it was so liberating. I didn't have a bad moment about it. It sort of reinvigorated my interest in a lot of things. I wonder if there should be some kind of anarchy.
Sean: You build a cage based on your sense of the truth and your sense of the aspects of the character that need to tell the story. If you've done your job right, which I've had varying degrees of success doing at different times in my life, then you're able to function very freely within that cage.
Sean: I was brought up in a country that relished fear-based religion, corrupt government, and an entire white population living on stolen property that they murdered for and that is passed on from generation to generation.
Sean: I think it's really important to be able to feel your own life, and I had felt so numbed by what had been a kind of surreal saturation of what was going on in the Middle East, and what it was going to mean, particularly relative to my kids' future and things like that.
Sean: I can never get ahead of the game because of the movies I do.
Sean: The major studios are by and large banks and they give you what is by and large a loan to make a movie. Like banks, they want their money back plus.
Sean: If the primary statement of the film is that if you have good abs it's OK to kill people, I pass.
Sean: Nic Cage is no longer an actor. He's more like a performer.
Sean: E.L. Doctorow had a quote I've used a lot of times, that the responsibility of the artist is to know the time in which he lives.
Sean: I've always operated under the notion that audiences don't always know when they're being lied to, but that they always know when they're being told the truth. And if there are what I think are unsung truths to be talked about in a film -- through a character, through a story -- and that dominates the piece, that's the key for me. I think the biggest thing is to not participate in the damaging, lying cinema.
Sean: The horror of the Academy Awards is what the press does leading up to it to make it a popular TV show. Where they'll actually make it like it's an arm- wrestling event between two actors. That becomes very petty, and that's something that's embarrassing to follow up with accepting the invitation to the party.
Sean: Your life is what you bring to any story. This is a life craft. It's 'How do you feel? Who are you? What do you have to say?'
Sean: There's an interesting parallel between Bush and Richard Nixon. While Nixon was clearly a superior statesman and in many ways a more intelligent politician, what they share is a kind of boldness in how they emote their insecurities. What we're finding with George Bush - part of what's familiar to people and that adds to his likability for many - is that there's a commonality of deep insecurity and his handling it with a kind of bravado. What they both did is handle things with a similar certainty - certainty being the "disease of kings.
Sean: ...I don't consider myself specifically political, you know? I think of working as an actor as being a human thing. The concerns I have that fall into politics are human concerns.
Sean: But the bigger issue is that it's an absolutely stupid notion that you should take the title of someone's profession and attach it to what they should not do. It has nothing to do with citizenry.
Sean: Hollywood is much more creatively corrupt than it is economically [corrupt]. It takes $1 for them to kill their dreams. Their dreams are worth more than $1.