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16 Totally Awkward Prom Photos: Celebrity Edition!

Brad Pitt's Prom Photo

It’s not just you and I who may have  awkward prom photos hidden away somewhere. Celebrities have them too!

To celebrate prom season, we’ve compiled a collection of 16 of the most awkward, awesome, and slightly embarrassing celebrity parent prom photos ever. From Brad Pitt to Michelle Obama to Jessica Alba, these are time capsules from years ago not just in the style of what they were wearing, their hairstyles, but how young they all were!

Check out these 16 prom photos from the days of yore right here:

(at left: Brad Pitt’s prom date seems to be glowing, and how could she not? She’s on a date with Brad Pitt.)

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  • Michelle Obama 1 of 15
    Michelle Obama
    Wow! Check out that saucy dress that Michelle Obama wore to prom. That is quite a Angelina Jolie's slit on the side. And love the wicker chair!
    image Via: Co-Ed Magazine
  • Will Ferrell 2 of 15
    Will Ferrell
    Proving that he has always been a jokester, Will Ferrell donned a tiara for his prom photo.
    image Via: Co-Ed Magazine
  • Jessica Alba 3 of 15
    Jessica Alba
    It's such a princess dress, pose and smile! I bet her girls would love this pic of her, but they'd probably wonder why daddy isn't with her.
    image Via: Super Booyah
  • Courteney Cox 4 of 15
    Courteney Cox
    Courteney seems pretty under-dressed for prom. But maybe that was just the style of the day.
    image Via: Oh No They Didn't
  • Britney Spears 5 of 15
    Britney Spears
    Britney's face looks so young, but that dress is so totally Dallas!
    image Via: Super Booyah
  • Sandra Bullock 6 of 15
    Sandra Bullock
    Sandra hasn't changed at all! Still that same sweet smile.
    image Via: Oh No They Didn't
  • Christina Aguilera 7 of 15
    Christina Aguilera
    It appears that Christina was part of a three person date! That's one lucky fella.
    image Via: Co-Ed Magazine
  • Meg Ryan 8 of 15
    Meg Ryan
    You've got to wonder what happened to Meg's date, she is looking at him so fondly.
    image Via: Super Booyah
  • Sarah Palin 9 of 15
    Sarah Palin
    Before she found her place in politics, Sarah Palin was doing things like going to prom. Notice the same kind of chair that is in Michelle Obama's prom photo. That's pretty much the only thing these two have in common.
    image Via: Super Booyah
  • Debra Messing 10 of 15
    Debra Messing
    Debra Messing was a teenager here but she looks more like a really hot mom! A very mature look.
    image Via: Oh No They Didn't
  • Snooki 11 of 15
    Snooki
    Snooki's prom photo! Pre Jersey Shore, pre hair bump and pre baby bump.
    image Via: Super Booyah
  • Halle Berry 12 of 15
    Halle Berry
    Yes, Halle Berry has always been regal.
    image Via: Co-Ed Magazine
  • Heather Locklear 13 of 15
    Heather Locklear
    Such a California girl!
    image Via: Co-Ed Magazine
  • Faith Hill 14 of 15
    Faith Hill
    Faith Hill (then Audrey Perry) was gorgeous then and she's gorgeous now.
    image Via: Oh No They Didn't
  • Paula Deen 15 of 15
    Paula Deen
    An oldie but a goodie. Here is a vintage shot of celebrity chef Paula Deen on her prom night.
    image Via: Oh No They Didn't
.

Above Photo Via: Super Booyah

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