260 voters

24 Times Sean Penn Acted Like a Douche

Updated September 23, 2021 1.3k votes 260 voters 15.1k views24 items

List RulesVote up the most infuriating Sean Penn moments.

Oh, Sean Penn. One minute, he was super tanned, high Sean Penn - the next he was super tanned, smug Sean Penn, shotgun-toting Sean Penn, threatening to punch fans Sean Penn, actually punching people Sean Penn, racist and homophobic children-raising Sean Penn, and farting near El Chapo Sean Penn. Seriously, what happened? Why are there so many Sean Penn stories that are so incredibly douchy?  

How did we get to Sean Penn annoying douche DEFCON levels? Hint: He was already there in the ‘80s. Now he’s fine-tuning his douchery. Let’s consider what happens when you’ve been famous for a long time: You believe the hype, you’re isolated from reality, and you actually mistake fame for importance.

What has made many label Sean Penn pretentious is his view that he’s an essential player in matters of foreign policy and disaster relief. And surely he’d done some good. He’s set up a relief foundation in Haiti, helped those in need after Katrina, and helped an American business man escape imprisonment in Bolivia, angering a lot of his leftist Latin American pals. He would say that he’s trying to help. But many see his input as, well, meddling (kind of like Dennis Rodman’s trips to North Korea).

Of all of his many douchey deeds, what makes Sean Penn annoying to you? His epic and rambling interview with El Chapo? That time he went off of on a fan for taking his picture? Him punching everyone in the ‘80s? Upvote your favorite Sean Penn douche moment and then tell everyone about it. That’s what he'd do!
  • 1

    When He Interviewed El Chapo for Rolling Stone

    Photo: Wikimedia Commons / CC-BY

    If this were an unedited chapter in a Hunter S. Thompson novel, it’d make sense. As intentional serious journalism, it’s something only Sean Penn would do. If you have the time to make it through the entire piece, you’ll get a real sense of Penn's writing style and his need to insert himself into the story at every turn. 

    Side note: Penn got El Chapo captured after all that careful tunneling and hiding. Don’t trust Sean Penn, drug lords.

    Photo: Sean Pean
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  • 2

    When He Went to Iraq Pre-Invasion to See Things for Himself and Meet with Tariq Aziz

    Penn wanted to see for himself what was happening in Iraq in 2003 and didn’t trust hundreds of news outlets, political experts, or the Internet. Instead of calling up any number of people who could fill him in on the subject, Penn went to Baghdad and met with Deputy Prime Minister Tariq Aziz, one of Hussein’s top aides, to get the full picture. 

    Photo: Tpbradbury / Wikipedia
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  • 3

    When He Met with Venezuela’s Hugo Chavez

    Video: YouTube
    Penn met with Hugo Chávez several times. He forged a friendship with the Venezuelan president that many just didn’t get. When Chávez died, Penn said, "Today the people of the United States lost a friend it never knew it had. And poor people around the world lost a champion. I lost a friend I was blessed to have."
    Then, in 2010, he went on Bill Maher's HBO show and suggested that anyone who called Chávez a dictator should be jailed. "Every day, this elected leader is called a dictator here, and we just accept it, and accept it. And this is mainstream media. There should be a bar by which one goes to prison for these kinds of lies.”
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  • 4

    When He Weighed in on the Falkland Islands

    Photo: flickr / CC0

    In 2012 Penn met with Argentinian President Cristina Fernández de Kirchner and decided to put pressure on the Brits to stop militarizing the South Atlantic. He urged Britain to join UN talks over what he characterized as “the Malvinas Islands of Argentina.” He also called Britain’s tactics in Argentina  "colonialist.”  

    Sean Penn is not going to bridge the gap between Argentina and Britain over the Falklands no matter how much everyone enjoyed Mystic River. A Parliament member called Penn’s comments “nonsense” and “moronic.” British Army vet Patrick Mercer also went after Penn’s IMDb credits saying, "A good number of his movies have been turkeys, so I suppose we shouldn’t expect much better coming out of his mouth."
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