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(#21) When He Overshadowed His Own Good Deeds in New Orleans
Penn knew he could afford to get on a plane and help as Katrina decimated New Orleans and the Gulf Coast. He evacuated a lot of people. He waded into the muck. He did a lot of good. And then he figuratively shot himself in the foot with one pic of him carrying a shotgun in the the Garden District in New Orleans. What was Penn going to do? Shoot looters? Take on rogue cops? Show the paps who's boss?
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(#4) When He Felt the Need to Stand Up to Chris Rock
A few years before the Hollywood Foreign Press set Ricky Gervais loose at the Golden Globes, Chris Rock managed to irritate a lot of people at the 2005 Oscars.
Rock made a crack about Jude Law’s over exposure at the time. “You want Tom Cruise and all you can get is Jude Law? Wait. It’s not the same thing. Who is Jude Law? Why is he in every movie I have seen the last four years? He’s in everything. Even the movies he’s not acting in. If you look at the credits, he made cupcakes or something. He’s in everything. He’s gay, he’s straight, he’s American, he’s British – next year, he’s playing Kareem Abdul-Jabbar in a movie.” Rock also went on to make the same joke about himself.
Penn, appointing himself the PC police of the Oscars, felt the need to stand up for Law when he went up to present the award for Best Actress saying, “Forgive my compromised lack of humor. I did want to answer our host's question about who Jude Law is. Jude Law is one of our most talented actors.”
To put that in perspective, consider Penn’s crack about Iñárritu getting a green card at the 2015 Oscars. -
(#23) When He Made Shanghai Surprise, Gave Madonna Street Cred
Not only is the film terrible, Penn’s street cred gave Madonna hope for an acting career. Yet, it’s still one of the best/worst movies to watch, like a craptastic appetizer before Showgirls. -
(#8) When He Covered the Iranian Elections for the San Francisco Chronicle
Five installments. 12,000 words. Penn takes readers to the elections, but he also walks them through every little detail about the stuff that happens to him. There’s a lot of Sean Penn in there. A lot.
Photo: Reese Erlich / The Chronicle
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(#18) When He Attacked a Paparazzo as a Grown Up Man
It’s one thing when you’re a young, hotheaded star; it’s another when you're a grown man. Penn pleaded no contest to vandalism and agreed to 36 hours of anger management plus 300 hours of community service following an assault on paparazzo Jordan Dawes in 2009. Penn was agitated that Dawes was snapping pics of him at the Brentwood Country Mart and kicked the photog.
Dawes received a settlement and made a surprising and ironic statement, "All of the net proceeds of the settlement will be donated to charities that support victims of domestic violence and victims of the earthquake in Haiti." His lawyer, Donald Karpel, also donated a portion of his attorney’s fees to the same charities. -
(#20) When He Was Arrested for Drunk Driving
Penn was quite busy in the ‘80s. When he wasn't launching himself at paps, he found time to climb behind the wheel while drunk - specifically in 1987, when he had a BAC of .11. The charge was later reduced to reckless driving.
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About This Tool
Sean Penn is one of the most eye-catching American actors and directors born in the last century. Sean Penn has always caused various controversies in his career. He has a bad temper, and when he is old, he still criticizes Hollywood everywhere, opposes the war, and cares about politics. But this famous "bad boy" has an extraordinary talent for acting, and the films he directs are often dark, real, and unique.
Sean Penn has always been known for his versatility and intense performances, you must also know some of his famous works. The random tool shows 24 times Sean Penn acted crazy.
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