30 Funniest Photos of Celebrities as Teens

Including one venerable talk show host you'll never recognize.

30 Funniest Photos of Celebrities as Teens

Including one venerable talk show host you'll never recognize.

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No amount of fame or fortune can take away the fact that every adult was once a teenager. And, as we’re all well aware, teen years are some seriously awkward years—yes, even for celebrities. Before the makeup artists and suave wardrobes, celebs were giant dorks, just like the rest of us.

Need proof? Here are 30 teen photos celebrities were brave enough to share with the world. They range from mildly awkward to painfully embarrassing to completely unrecognizable. So read on And while they’re all good for a laugh, even the worst of them is nothing compared to the The 20 Funniest Celebrity Mugshots.

Abbi Jacobson as a teen.

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Abbi Jacobson

Looks like even Broad City star Abbi Jacobson fell prey to the unfortunate crushed velvet fad happening in the ’90s. The mantle-showcasing pose is pretty awkward too, but not as awkward as the 30 Most Awkward Celebrity Awards Show Moments.

John Mulaney as a teen.

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John Mulaney

When you’re a regular teen, you don’t get to request post-production services on your photos. This eyes-closed homecoming photo of John Mulaney is pretty funny, but it’s nothing compared to the 30 Most Hilarious Celebrity Instagram Photos.

Kaitlin Olson as a teen.

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Kaitlin Olsen

“You take the thinnest layer of hair possible, and you curl it as though the most delicate sausage in the world were laying across your forehead.” A very good description of her hairdo by It’s Always Sunny in Philadelphia star Kaitlin Olson, but not quite good enough to make it onto the 15 Top Hair Tips from Top Hollywood Stylists.

Aidy Bryant

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Aidy Bryant

There was just something about picture day that made everyone think a striped turtleneck seemed like a good choice. Hindsight is 20/20.

Eric McCormack as a teen.

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Eric McCormack

Before Eric McCormack was Will on Will and Grace, with hair like that, he could’ve done part time work as a stand-in for Chachi.

Ryan Seacrest with his Mom.

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Ryan Seacrest

It’s hard to believe this is Ryan Seacrest. But he swears it is. And why would anyone make that up?

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John Oliver

If he’s comfortable sharing this photo, John Oliver probably doesn’t need 70 Genius Tricks to Boost Your Confidence.

Awkward Lena Headey on a horse.

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Lena Headey

Game of Thrones star Lena Headey’s casual horseback attire was probably very cool at the time, but “it’s okay to wear socks with sandals” should be on the list of 25 Life Lessons You Learned as a Kid That Are Wildly Outdated Today.

Alison Brie as an awkward juvenile.

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Alison Brie

Compare this pic of Alison Brie as a headgear-toting teen to Alison Brie today, and you might start to believe anything is possible.

Chelsea Peretti as a teen.

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Chelsea Peretti

This picture of Chelsea Peretti perfectly encapsulates the face any teen would make if their parents insisted on photographing them in this ensemble.

Young Jake Tapper

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Jake Tapper

Jake Tapper, on the other hand, has apparently been dressing the part of CNN anchor since he was a child. Good for him.

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Clark Gregg

As a teen, Clark Gregg somehow cracked the code on how to straddle the line between totally suave and totally embarrassing. Maybe it’s the curtain?

Nick Kroll in a suit

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Nick Kroll

Even at a young age, Nick Kroll was dressing like a comedian. Unfortunately, comedians back then wore shiny double-breasted suit jackets and polka dot ties.

Andrew Rannells school photo

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Andrew Rannells

Surprisingly, Andrew Rannells’s hair style hasn’t changed that much since he was a schoolkid. It just looks a lot better now.

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Brandon Flynn

Hopefully 13 Reasons Why star Brandon Flynn checked with his old friend before he shared this picture on Instagram.

Cool Dinklage

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Peter Dinklage

Peter Dinklage managed to make his awkward years look cool, despite having a mullet. A feat not many can pull off.

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Reese Witherspoon

This is about as awkward as Reese Witherspoon gets. Must be nice!

Young Conan O'Brien

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Conan O’Brien

“This photo was taken the day I replaced David Letterman,” according to a not-salty-at-all Conan O’Brien.

Maya Rudolph school pic

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Maya Rudolph

As a child, Maya Rudolph understood the importance of good accessories and good hair when you’re being photographed from the neck up.

Martin Short on the beach

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Martin Short

“This was during a phase when jazzercize was not so important,” according to Martin Short.

Andy Cohen yearbook photo

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Andy Cohen

Andy Cohen’s come a long way since this yearbook photo was taken. Ditching the glasses was probably an important first step.

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Jimmy Kimmel

If the license plate in this photo is any indication, Jimmy Kimmel has had his eye set on a late night gig since he was just a boy in short shorts.

Young Ruby Rose

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Ruby Rose

Before playing tough gals for a living, Ruby Rose was apparently a tough looking gal in real life.

Topher Grace yearbook photo.

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Topher Grace

It’s hard to believe this pic was taken just six years before That ’70s Show went on the air. A little bit of time can make a lot of difference when it comes to being an awkward adolescent.

Young Sarah Silverman

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Sarah Silverman

Young Sarah Silverman was too busy playing ball to make time for any nonsense.

Josh Gad in a fabulous hat

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Josh Gad

This middle school-era picture of Josh Gad really showcases the dangers of putting on a novelty hat at a party.

Young Melissa Rauch

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Melissa Rauch

Looks like The Big Bang Theory star Melissa Rauch was another hapless teen who couldn’t resist the temptation of curling iron abuse.

Teen Patton Oswalt playing a saxophone

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Patton Oswalt

Apparently Patton Oswalt believes “all my adolescent pics are 100% awesome.” If this is any indicator, he’s not wrong.

Henry Winkler as a child.

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Henry Winkler

Loosened tie, ice cream dangling from his mouth—from the looks of it, Henry Winkler started rehearsing for his role as the Fonz at a very young age.

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Stephen Colbert

“Nick Kroll asked me to post a pic of my awkward stage, but I never had one. So here’s me lookin’ cool!” And for more on the consummate late-night host, be sure to check out The 30 Most Outrageous Late-Night TV Moments Ever.

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