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23 Embarrassing Celebrity Prom Photos

Topanga and Lance Bass

It’s prom season, so let’s take a look back at some super embarrassing celebrity prom photos to make ourselves feel better about our own questionable fashion choices! Yay!

Topanga and Lance Bass

Topanga and Lance Bass
I don’t care if her real name is Danielle Fishell. Her real name is Topanga to us.
(source)

Lucy Hale

Lucy Hale Will Ferrell
Lookin’ more like Lucy KALE! (But no really this is too many ruffles for one body.)
(source)

Sylvester Stallone

Sylvester Stallone Will Ferrell
I can still hear Sylvester’s voice through this picture.
(source)

Ellen DeGeneres

Ellen DeGeneres Will Ferrell
Ellen isn’t happy because she’d rather be wearing her date’s outfit. (We all would).
(source)

John Stamos

John Stamos Will Ferrell
John Stamos takes Little House on the Prairie to prom.
(source)

Jon Hamm

Jon Hamm Will Ferrell
He hadn’t grown into his Draper yet.
(source)

Matthew McConaughey

Matthew McConaughey Will Ferrell
Not alright, not alright, not alright. (I’m talking about his date’s dress. He’s cute af.)
(source)

Barack Obama

barack Obama prom
BUT WHY DIDN’T HE ROCK THE FRO THROUGHOUT HIS PRESIDENCY?!
(source)

Will Ferrell

Will Ferrell prom
This couldn’t be more Will Ferrell.
(source)

Britney Spears

Britney Spears prom
It’s okay, Brit, none of us knows what to do with our hands in these pictures.
(source)

Tupac Shakur

Tupac Shakur prom
Tupac Shakur lookin’ suave af and wayyyy too old to be at a prom.
(source)

Jessica Alba

Jessica Alba prom
That dress is only okay if the prom theme was “Swan Lake”.
(source)

Jimmy Fallon

Jimmy Fallon prom
Wonder if he was as terrible at fake-laughing back then…
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John Krasinski

John Krasinski prom
Jim! This is totally Jim from The Office at prom!!
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Jennifer Aniston

Jennifer Aniston prom
#ItGetsBetter.
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Taylor Lautner

Taylor Lautner prom
Ahh, the late ’90s spikey hair. RIP.
(source)

Lizzie Caplan

Lizzie Caplan prom
$20 to the person who can tell me what Lizzie Caplan did to her hair.
(source)

Angelina Jolie

Angelina Jolie prom
Angelina Jolie — The Steve Buscemi Years.
(source)

Blake Lively

Blake Lively prom
Blake Lively WOULD wear the tiara before even getting to the prom.
(source)

Taylor Swift

taylor swift prom
I wonder what gang Taylor Swift was in?
(source)

Brad Pitt

Brad Pitt prom
Brad Pitt: The I’m Still Brad F*cking Pitt, Bitches Years 
(source)

Which of these prom looks do you think is the most embarrassing? And seriously though, wtf happened to Lizzie Caplan’s hair?!

Contributor: 
Cat Pajamas
View Count: 
148
Weekly View Count: 
148
Mass images: 
Topanga and Lance Bass
Lucy Hale Will Ferrell
Sylvester Stallone Will Ferrell
Ellen DeGeneres Will Ferrell
John Stamos Will Ferrell
Jon Hamm Will Ferrell
Matthew McConaughey Will Ferrell
barack Obama prom
Will Ferrell prom
Britney Spears prom
Tupac Shakur prom
Jessica Alba prom
Jimmy Fallon prom
John Krasinski prom
Jennifer Aniston prom
Taylor Lautner prom
Lizzie Caplan prom
Angelina Jolie prom
Blake Lively prom
Brad Pitt prom
taylor swift prom

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