The Most Amazing & Awkward Celebrity Prom Photos


Celebrities – they’re just like us. Except for the money. And the fame. And the power. And the awards. 

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Jennifer Aniston

Before Jennifer Aniston had her iconic Friends haircut, she had…this. She looks stunning as long as you keep your eyes below her forehead. 

John Stamos

Have mercy! (Also, this photo explains why John Stamos doesn’t appear to age…when he was 17 he looked 12—so I guess he was just blessed from the start!)

Lady Gaga

We barely recognized this as Lady Gaga at first. And something tells me she would probably prefer that. 

Matthew McConaughey

Alright, alright, alright—what a dapper young gentleman! Seriously, when’s the last time his hair was so short??

Reese Witherspoon

About what we’d expect the Southern Belle to look like at her prom!

Sandra Bullock

Wonder how long that intricate updo took her!

Britney Spears

Wait, who’s the old guy behind her? And even more importantly, if that’s her date, why doesn’t his tie coordinate with her dress?! This is Prom 101, people.

Will Ferrell

Will Ferrell – America’s funniest prom queen. I’m sure he waged a brutal campaign to win the honor. 

Taylor Swift

Taylor Swift should have either stuck with a white dress or a fake tan – they cannot coexist. But bad fashion choices are what make prom so fun. 

Jimmy Fallon

It’s a good thing that Jimmy Fallon grew out of that awkward teen look. It’s unfortunate, however, that he transitioned immediately into an awkward adult look. 

Faith Hill

How did we not know Faith Hill went to prom with Napoleon Dynamite?! Also…she has a giant corsage AND a bouquet? Is this prom or her wedding?


Usher clearly developed his love of white clothing young. 

George Clooney

It’s an old photo, but if you look closely, you’ll clearly see George Clooney rocking a mullet. It’s obviously time to cancel him. 

Kim Kardashian

The only jokes I can come up with are about seeing Kim’s original nose, so I’ll just let the photo speak for itself.

Ellen DeGeneres

Okay, time to pack it up and go home. Ellen DeGeneres clearly has the best worst prom photo of all time. She might be a snazzy dresser now, but this is some peak ’70s fashion. 

Bruno Mars

Is this photo even real? It’s so peak awkard prom that I’m struggling to believe something so perfect could exist. Bruno Mars is somehow simultaneously rocking and not rocking that hair. 

Lance Bass/ Danielle Fishel

For whatever reason, Topanga from Boy Meets World and a gay boy band member went to prom together. The late 90s were a strange time…


Do you think that Rihanna and her date coordinated their hairstyles or was that just an unfortunate coincidence? At least she matches with the prom decor!

Nick Kroll

I didn’t think it was possible to love Nick Kroll more, but this picture achieved the impossible.

Meryl Streep

And here’s Meryl Streep’s prom photo, proving that she’s always been a queen!

Claire Danes

Claire Danes really lucked out in the awkward prom photo department. I see a few chunky, blonde highlights but nothing too obnoxiously retro.

Amy Poehler

No, unfortunately this isn’t an old Saturday Night Live skit. It’s a real photo from Amy Poehler’s real prom. But I understand the confusion.

Ashton Kutcher

Welp, looks like nothing’s changed here!

Michelle Obama

If Michelle Obama’s (admittedly amazing) shiny, peach dress didn’t let you know this was the 80s, the giant wicker chair she’s sitting in should do the trick. 

Amanda Seyfried

One look at the hairstyles in this lineup and you know we’re dealing with the early 2000s. And Amanda Seyfried doesn’t look a day older than she does now. So…super jealous. 

Carrie Underwood

Those bangs…!

Gwen Stefani

Ok, I had to do a double take on this one. I 100% thought this was Carrie Underwood at first. When did Gwen go from Little Miss Proper to the punk rocker we know and love today?

Scarlett Johansson

I’m not sure what’s worse…her prom outfit or the iconic ’90s blue eyeshadow.

Snoop Dogg

Did anyone else expect Snoop’s prom photos to be a bit more outrageous? No? Just me?

Harry Styles

He’s been out of school for almost a decade, and yet Harry Styles looks nearly the same. And even though he’s probably used to cameras in his face now, he still managed to pull off an awkward prom smile here. 

Published by everbly


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