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  • When He Let His Kid Say Racist and Homophobic Things to a Paparazzo on Random Sean Penn Acted Like a Douche

    (#14) When He Let His Kid Say Racist and Homophobic Things to a Paparazzo

    Yes, paps are pretty bad - intrusive, prying, provocative, and worse. But TMZ photogs are actually a step above most. In the video, the TMZ pap is on a public sidewalk when Penn’s son, Hopper, bumps him, gives him the finger, and then calls him racist and homophobic names. The pap rightly asks, “That the kind of talk you’re teaching him, Sean?”

    Hopper Penn non-apologized later, saying, “I was accosted by paparazzi and made to feel like an animal - threatened and under attack, but that does not condone my own actions… I deeply regret my choice of words."
  • When He Punched an Extra on the Set of Colors in 1987 on Random Sean Penn Acted Like a Douche

    (#17) When He Punched an Extra on the Set of Colors in 1987

    If you think 50-something Sean Penn is hot headed, 26-year-old Sean Penn was out of control. He punched Jeffrey Klein, an extra, on the set of Colors while shooting in Venice. Penn punched Klein because he was taking pictures of Penn and fellow star Robert Duvall. But he didn’t just punch Klein. He punched him several times and had to be pulled off of Klein. Penn served just a little over half of his 60-day jail sentence.

    Photo: Orion Pictures
  • When He Covered the Iranian Elections for the San Francisco Chronicle on Random Sean Penn Acted Like a Douche

    (#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
  • When He Peed in a Bottle in Front of a Reporter on Random Sean Penn Acted Like a Douche

    (#7) When He Peed in a Bottle in Front of a Reporter

    During an interview with Rolling Stone, Penn decided to relieve himself into some bottles in front of the reporter, Chris Munday. Munday wrote: 

    “He recites jokes, he tells stories, he finishes urinating. Almost. ‘I need another bottle,’ says Penn.

    He sets the brimming vessel in front of him, and the room erupts with laughter. He of the enormous bladder grins, and a second bottle is placed in his left hand before it quickly disappears under the tablecloth. . . . Relief.”
  • When He Wrote an Open Letter to Matt Stone and Trey Parker on Random Sean Penn Acted Like a Douche

    (#9) When He Wrote an Open Letter to Matt Stone and Trey Parker

    Penn had no trouble with Parker and Stone making fun of him in Team America: World Police, but he did not like Stone’s comment about voting in an interview for Rolling Stone. Stone said, “If you don't know what you're talking about, there's no shame in not voting." Instead of calling Stone like a grown up and saying, “Hey, I took offense at what you said," Penn wrote an open letter.

    Penn wrote:  

    “I do mind when anybody who doesn't have a child, doesn't have a child at war, or isn't or won't be in harm's way themselves, is encouraging that there's "no shame in not voting" "if you don't know what you're talking about" (Mr. Stone) without mentioning the shame of not knowing what your [sic] talking about, and encouraging people to know. You guys are talented young guys but alas, primarily young guys. It's all well to joke about me or whomever you choose. Not so well, to encourage irresponsibility that will ultimately lead to the disembowelment, mutilation, exploitation, and death of innocent people throughout the world. The vote matters to them. No one's ignorance, indcluding [sic] a couple of hip cross-dressers, is an excuse.  

    All best, and a sincere f*ck you,  
    Sean Penn”  

    What did Parker and Stone think of it?

    Parker: Sean Penn was brave enough to send us a letter. It’s so funny that he wrote a little letter. 'Let me write a letter. I’m official. This is an official document.' The thing that’s so funny is our lawyer actually called us after the letter hit The Drudge Report because we got it before it hit The Drudge Report. Our lawyer honestly thought that we did it. He’s like, “Did you guys write that letter because it sounds like you wrote it?” I’m like “No. You know that was really Sean Penn.”  

    Stone: He couldn’t have done us a bigger favor. There’s nothing he could have done to help us out more. So it was just really strange.
  • (#2) When He Went Ballistic on a Fan Who Took a Picture

    We get it, you’re famous and not always in the mood to have your picture taken in public, and especially not in a packed bar in a popular hotel in a major city. But is it necessary to go crazy on a regular Joe when they take a pic?

    Penn launched himself at a guy in an upscale San Francisco hotel bar when the fan tried to take a picture of Penn on his phone. The guy was not a paparazzo; he was a sales conference attendee at which Penn had spoken earlier. So when he moved in for a shot with his cell, Penn yelled, “I’ll make you eat the phone!” and, “Do we look like f—king zoo animals?!”

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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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