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20 Most Awkward Celebrity Prom Photos

Don't worry, celebs had awkward dates, gigantic dresses and cringe-worthy hair, too
Photo 1/20
Michelle Obama
With a killer slit and tons of satin, Michelle Obama looked ready to rule the world at her prom. If only every high school provided an ornate throne for portraits.

Photo 2/20
Ellen DeGeneres
We bet Ellen DeGeneres's dance moves on the floor were just as amusing as her plaid, collared prom dress.

Photo 3/20
Christina Aguilera
Christina Aguilera was truly ahead of her time. Not only was she opened-minded enough to apparently share a prom date, she also posed with today's much loathed and loved duck face.

Photo 4/20
Jennifer Aniston
Thanks to reruns of "Friends," we were expecting an entirely different '80s 'do on Jennifer Aniston, but we think the voluminous perm makes the birth of "The Rachel" that much more dramatic.

Photo 5/20
Tyra Banks
Tyra Banks hadn't nailed "smizing" in high school, but she still looked every bit the supermodel in an elegant all-black ensemble.

We all know pictures of Kate Hudson with a Jamba Juice and Jessica Alba pushing a Target shopping cart do not, in fact, make celebrities" just like us." Clearly, it's old prom photos showcasing hideous '80s hair, regrettable prom dresses and the effects of puberty that do.

To even the playing field, we dug up a bunch of celebrity prom pictures that transport us back to a magical time when A-listers and red carpet regulars weren't so different from you and me. Here, the #ThrowBackThursdays and #FlashBackFridays celebs hoped you wouldn't see.
JUL 23, 2009 | SHARES
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