Sean Penn: Hollywood’s Red Carpet Grumpus

Photo: Frank Trapper/Sygma/Corbis,Pascal Le Segretain/Getty Images,Ann-Christine Poujoulat/AFP/Getty ImagesFrank Trapper/Sygma/CorbisAnn-Christine Poujoulat/AFP/Getty Images

It's awards season, which means practically every day brings a new wave of shots of smiling celebrities. And every batch of professionally grinning stars further shines a light on one anomaly: Sean Penn, a man who is innately unable to muster up any joy on a red carpet. He’s like an unhappy cat shoved into a penguin suit. He has been a star for more than 30 years, and there is something impressive about his stubborn resentment of all things flash-bulbed. He saunters his way through every gala with a fixed scowl, as if he were part bull and trying to hold back his seeing-red rage. Simply put: He’s the anti–Anne Hathaway. Below, stroll through a history of Sean Penn begrudgingly walking the red carpet. Or maybe he’s actually only pretending to hate it; it’s hard to tell — the man’s a great actor.  

Photo: Ron Galella/WireImage

1989, We're No Angels Premiere: That cigarette is all that stops him from either frowning or shouting about how he wants to be frowning.

Photo: Frank Trapper/Sygma/Corbis

1992, Screening of Chaplin: He just looks like that because he bought his shoes at that Payless to his left. Maybe it doesn't feel good to pay less.

Photo: Frank Trapper/Sygma/Corbis

1995, The Crossing Guard Premiere: "Your flashes! They burn! I'm melting. I'm melting. Ha-ha! Anyway, Wizard of Oz references aside, I fucking hate this."

Photo: Frank Trapper/Sygma/Corbis

1996, Moll Flanders Premiere: "Maybe if I lean back hard enough, I'll start moving backward and off this red carpet. Damn your forward momentum, Robin, you are ruining everything!"

Photo: J. Vespa/WireImage

1999, Sweet & Lowdown Premiere: "Consider this hair a line graph charting my drop in joy during this part of the evening. More like 'lowdown and not sweet premiere.'"

Photo: Chris Weeks/Getty Images

2001, The Pledge Premiere: "Okay, tonight, since it's a movie I directed, I'll enjoy myself and ... What's that, Mr. Paparazzi? Say 'cheese'? I once had a cat named Cheese who we had to put to sleep. Nice going; now I'm pissed again!"

Photo: George Pimentel/WireImage

2002, Toronto Film Festival: "Fine, I won't frown, but my mustache sure will." (A phrase Penn loved so much, he eventually tattooed it over his heart.)

Photo: Pascal Le Segretain/Getty Images

2007, Rome Film Festival: Wait! Sunglasses seem to be the key to his happiness! Turns out he was only angry about the way the flash bulbs hurt his eyes! Problem solved!

Photo: Pascal Le Segretain/Getty Images

2008, Cannes Film Festival: Woof. Never mind.


2008, Cannes Film Festival: We've been having some fun here, but in this one, he looks seriously pained and legitimately sad. Who is forcing this man to make these appearances?

Photo: Jason Merritt/Getty Images

2009, Academy Awards: Finally! The only surefire way to get a smile out of Penn is to put an Oscar in his hand. It's downright Pavlovian, though much harder to arrange than ringing a bell.


2011, The Tree of Life Premiere: "What are you jerks smiling at? Don't you know we're on the red carpet? Is it because you're both so pretty? Oh, it is? Carry on then."

Photo: Andreas Rentz/Getty Images

2011, This Must Be the Place Premiere: "Finally, people on my grumpy wavelength. Let's get this party started! And by 'started' I mean let's sulk in the beat."

Photo: Tony Barson/FIlmMagic

2012, Cannes Film Festival: The good news is he isn't frowning. The bad news is it seems like all these years of red carpet flashbulbs have driven him to madness.

Photo: Frederic J. Brown/AFP/Getty Images

2013, Gangster Squad Premiere: New year, new movie, new outlook on red carp— Nope. Same outlook. Even his hair looks like it's frowning.