20 Rare Celebrity Prom Photos That Are Even More Awkward Than Yours Was

In 2013 Jimmy Fallon tweeted this picture of himself at his prom with the caption “My date went tanning the night before. I did not. I looked like powder #awkwardpromstory.” But, pale vampire face aside, that’s not such a bad picture in comparison to other prom pics of current celebrities from way back when.

Just like the rest of us, these soon-to-be-famous folks spent their prom nights looking awkward or ridiculous – but unlike the rest of us, their shameful shots have gone round the world after they hit the big time. Well, there are bound to be some drawbacks to fame, right?

19. Taylor Lautner

Way before his hunky Twilight days, Taylor Lautner was a fresh-faced, spiky-haired little tyke. Sadly, we’ll never know whether he’d have picked up so many fans if he’d kept on with that human hedgehog look. Probably not.

18. Lizzy Caplan

Actress Lizzy Caplan’s prom picture is strange to say the least, but what’s the strangest thing about it? The bizarre knotted hairdo? The piercing stare of exasperation on her face? Or the fact that her date is dressed as a Dalmatian? Could be any of those things, let’s be honest.

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17. Ellen DeGeneres

Has anyone ever looked more miserable in their prom picture than Ellen DeGeneres? Still, if we were stuck with a dress as magnificently ugly as that, we’d be a bit down in the dumps too.

16. Lance Bass

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If Lance Bass’ date here looks familiar, then that’s because he’s draped over none other than Topanga from Boy Meets World, aka actress Danielle Fishel. However, even her surprising presence can’t quite distract from the awkwardness of the onetime NSYNC star’s hovering hands, pained expression and blonde frosted tips.

15. Brad Pitt

Believe it or not, even Brad Pitt once had a phase where he just looked like a regular kid with a bad haircut, instead of a sex god bound for Hollywood stardom – as his cringeworthy prom pic here shows. That bizarre, half-laughing facial expression on the face of the future hunk doesn’t really help his case, either.

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14. Renée Zellweger

There’s something more than a little unnerving about Renée Zellweger in her prom pic. The smile, the blank eyes and the hand just floating above her date’s chest all just seem slightly menacing when you put them all together in one shot. The ’80s hairdo actually rather suits the future actress, though, so there’s that.

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13. Pamela Anderson

Baywatch sex symbol Pamela Anderson looks completely and utterly unrecognisable in her prom pic. No peroxide blonde hair or red one-piece here – just brunette curls and a terrible, puffy white dress. She still looks gorgeous, though, despite that awful choice of gown.

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12. John Stamos

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If ever anyone doubted that Full House’s John Stamos had a healthy sense of humor, then the fact that he shared this both adorable and utterly awkward prom shot on Instagram should convince them of that fact. After all, it’s healthy to poke fun at your young self’s terrible suit and hair flicks now and again.

11. Angelina Jolie

Angelina Jolie would grow up to be considered one of the most beautiful women in the world. But this prom photo shows that once even she was an awkward, gangly young person. Hope for all teens tussling with their looks, then.

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10. Jon Hamm

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Jon Hamm may have already been as dapper as Don Draper in his youth, but at this point he hadn’t quite mastered a smile yet. Hopefully that awkward grimace didn’t disappoint his cute date – future 24 and Twilight actress Sarah Clarke – too much.

9. Sylvester Stallone

Who’d have known that this gawky kid would have grown up to become one of the most iconic tough guys in Hollywood? Probably not Sylvester Stallone at this point: he’s 19 years old here and your standard-issue graceless teen.

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8. Paul Rudd

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With a mullet like that, it’s remarkable that Paul Rudd managed to get even one girl to pose near him, let alone three. The fact that the hairdon’t was pretty much the style at the time doesn’t stop the shot from now raising a bit of a chuckle, though.

7. Bruno Mars

Before he settled on his current look, Bruno Mars – or plain old Peter Hernandez, as he was then – was rocking an afro. And the future pop star pretty much pulls it off, so it’s the pose that makes this shot awkward: scarily, it looks like his date is about to strangle him.

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6. Matthew McConaughey

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Let’s hope that Matthew McConaughey grew out of being surprised every time a camera is pointed at him. After all, there are plenty now pointed at him during his day job.

5. Ryan Seacrest

Where to start with Ryan Seacrest’s pic? His hair, his date’s spectacular dress… oh, and also neither of them look like they’re really sure where to put their hands. Probably a snap he’d rather were pushed to the back of a cupboard, really.

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4. John Krasinski

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Teenage John Krasinski had yet to settle into his ears, or teeth, or… well, any of his body, really. Anyone who grew up hot and married Emily Blunt has got to have had the last laugh, though.

3. Elizabeth Banks

Elizabeth Banks looks quite pretty in her prom photo, even with that ever so slightly ill-judged hair. And that half-smile, half-grimace, too. Perhaps her date is holding her a bit too tightly.

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2. Jennifer Aniston

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A long time before the “Rachel,” Jennifer Aniston sported this unflattering ’do instead. Her date looks like he didn’t care, though – and now he has bragging rights for days.

1. Josh Duhamel

The future Mr. Fergie looks very confused in his prom picture. Is it because, as Josh Duhamel himself has said, he’s realized that he might get to see a girl naked for the first time and is so puzzled as to what she might look like? Or is it just because he’s wondering about that thing on his head?

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