Entertainment

30 Celebrities Who Tried To Make Winking Look Good, From Miley to Hillary

I am impressed with anyone who can pull off a sly wink without looking like their eye has taken on a mind of its own. I am not one of those people. I've tried (and failed) to do the whole "sassy wink thing" in pictures and it always ends up looking like I've fallen asleep before the person could snap the photo. Luckily, I'm not alone in epically failing at the 80s movie made pose. Check out these 30 photos of celebrities who tried to make winking happen.

by Kaitlin Reilly

Nick Cannon

Pretty much how Cannon always takes photos.

Christopher Polk/Getty Images Entertainment/Getty Images

Marc Anthony

That’s the face I make when I’m putting on mascara.

Mario Tama/Getty Images Entertainment/Getty Images

Gerard Butler

Forget the wink. Remember when that hair was a thing?

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Madonna

The hat makes the look.

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Kate Beckinsale

Get sassy with it.

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Chloe Grace Moretz

She’s keeping one eye open so she can check on the rest of the action.

Tullio M. Puglia/Getty Images Entertainment/Getty Images

Barack Obama

The smirk!

Chip Somodevilla/Getty Images News/Getty Images

Robert Downey Jr.

Iron Man gets goofy with this wink.

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Gisele

Careful with those, girl. You can only see out of one eye.

Evan Agostini/Getty Images Entertainment/Getty Images

Christina Aguilera

The commitment is so good.

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Miley Cyrus

One of Miley’s eyes if having a party in the USA, and the other is like, “No, don’t worry, you go on ahead… I have a lot of Sons of Anarchy to catch up on.”

Frazer Harrison/Getty Images Entertainment/Getty Images

Hillary Clinton

Thankfully, winking is not a political platform.

Win McNamee/Getty Images News/Getty Images

Sofia Vergara

Possibly born winking.

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Jennifer Lopez

Like Lopez could ever look bad doing anything.

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Lindsay Ellingson

The weirdest thing about this photo is really the fact that her outfit is a bra, panties, and Christmas sweater.

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Monique

Kind of loving the pink eyeliner.

Frederick M. Brown/Getty Images Entertainment/Getty Images

George Bush

Very unclear as to whether this wink was intentional.

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Vivica Fox

Well, at least her hair looks amazing.

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Debbie Ryan

You know that they teach this skill over at Disney.

Michael Loccisano/Getty Images Entertainment/Getty Images

Lindsay Lohan

This is what winking is supposed to be. Take note, people.

Kevin Winter/Getty Images Entertainment/Getty Images

Jamie Chung

Okay, okay… the Once Upon a Time star really has nailed winking. And she gets to be married to Bryan Greenberg, because life is fair.

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Miley Cyrus

She’s just being Miley. Again.

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Snoop Dogg

I think the braids make it.

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Maria Menounos

With hair that amazing you have to think she’d have shortcomings in at least one area. This is that area.

Lawrence Lucier/Getty Images Entertainment/Getty Images

Emilio Estevez

Half of Estevez’s body looks asleep in this photo.

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Stanley Tucci

Well, I guess we finally found something that Tucci isn’t good at.

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Damien Lewis

Lewis looks like he’s trying reallllly hard to close at least one of those eyes.

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Madonna

Thankfully, Madonna has enough sass in one hair follicle that this winking actually kind of works.

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Adriana Lima

Girl is gorgeous even when it looks like she’s snarling at the camera.

Bryan Bedder/Getty Images Entertainment/Getty Images

Freema Agyeman

The former Carrie Diaries star is as coy as her character Larissa.

Jason Kempin/Getty Images Entertainment/Getty Images
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