Entertainment

24 Times Sean Penn Acted Like a Douche

List Rules
Vote 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
    62 VOTES

    When He Covered the Iranian Elections for the San Francisco Chronicle

    When He Covered the Iranian Elections for the San Francisco Chronicle
    Photo: flickr / CC0

    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
  • 2
    70 VOTES

    When He Went Ballistic on a Fan Who Took a Picture

    When He Went Ballistic on a Fan Who Took a Picture
    Video: YouTube

    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?!”
  • 3
    87 VOTES

    When He Met with Venezuela’s Hugo Chavez

    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.”
  • 4
    25 VOTES

    When He Chain Smoked While On Ambien During A Colbert Interview

    When He Chain Smoked While On Ambien During A Colbert Interview
    Video: YouTube

    In March 2018, Penn stopped by the The Late Show with Stephen Colbert to promote his debut book (which was met with almost universally scathing reviews). Penn didn't appear to make much of an effort to be entertaining - or even fully cognizant - during the interview. In fact, he told Colbert he was still feeling the effects of the prescription sleep aid Ambien he had taken the night before. Right after this confession, he lit up a cigarette and proceeded to chain smoke throughout the interview. 

    The conversation itself was a bit long and rambling, with Penn circling around a variety of topics unrelated to his novel. He blasted Hollywood, claiming the politics and bureaucracy drove him away, and said some of his collaborative projects had been nightmares. However, Penn clearly did not feel he shouldered any of the blame for failed projects, saying, "I was never disappointed with me."