HomeBeauty+Style28 Hilarious Celebrity Prom Photos That Prove Everyone Was Awkward In High...

28 Hilarious Celebrity Prom Photos That Prove Everyone Was Awkward In High School

Taylor Swift

What is more embarrassing than two suburban rich kids throwing up some gang signs? It’s okay Taylor, the past is the past.

Will Ferrell

We love that funnyman Will Ferrell was always true to himself! The tiara was a hilarious touch to a great look. Not embarrassing one bit. We love it, Will!

Bruno Bars

Let’s give it up for the ultra progressive Bruno and his girlfriend sporting the “reverse prom pic” pose in this photograph.


Okay so there isn’t anything particularly embarrassing about RiRi’s look… except for her date.


Okay so there isn’t anything particularly embarrassing about RiRi’s look… except for her date.

Blake Lively

Oh no. We like to think that Blake was just a tragic victim of 2000’s fashion. However, she comes from a famous Hollywood family,so we had higher expectations.

Britney Spears

The pop princess was on fire at her high school prom in this fiery red dress.

Brad Pitt

Brad Pitt was a wonderful date when he attended prom in 1982. He apparently taught his date how to dance to Michael Jackson’s hit “Rock With You.”

Lady Gaga

The thing is, Lady Gaga’s prom outfit is one of her more dare we say, “normal,” looks.

Demi Lovato

Demi had actually been dating a Jonas brother at the time, but was fulfilling a promise she had made to her childhood friend. The Disney star escorted her date in her hometown of Dallas, Texas.


Bedazzled gown, over-the-top-gloves. Is this a picture of Fergie at her prom or is it an advertisement for the terrible fashion era of the 1990s? Seriously, she could be the poster child for celeb prom catastrophes.

Jessica Alba

Jessica Alba’s milkmaid halloween costume… I mean prom dress… stole the show. We must say, her date looks like he is on cloud nine.

Ellen Degenres

The HORROR! Ellen actually admits that this was a particularly low point in her life. We want to know if her miserable expression is a result of her date, or her 70’s mullet and drab plaid dress.

Jimmy Fallon

He has come a long way since those unfortunate pimple face days. Actually, this photo was taken only 6 years prior to his SNL debut!

Danielle Fishel

By the time her senior prom came around, Danielle Fishel was already famous as the star of Boy Meets World. That being said, it only made sense for her to be escorted by N’SYNC’s Lance Bass, who has since changed his sexual preference. Can someone say AWKWARD??

Kim Kardashian

Alright, we know Kim didn’t go to high school in the 50’s, what’s with the photo quality?

Scarlett Johansson

Scarlett Johansson is a Hollywood beauty, but even her prom photo is embarrassing. Johansson and Jack Antonoff went to prom together back in 2002.

George Clooney

Even in 1978, George Clooney had a way with the ladies and no problem getting a date for his high school prom.

Jennifer Anniston

As always, Jennifer Aniston keeps it classy in an elegant black dress for her high school prom.

Jon Hamm

Jon Hamm isn’t the only star in this photo, he had the pleasure of taking Sarah Clarke to their high school prom.

LeBron James

LeBron James and, his now wife, Savannah Brinson were high school sweethearts! They attended prom while she was five months pregnant with their first child, LeBron Jr.

Ryan Seacrest

Even Ryan Seacrest can’t escape the embarrassment of a high school prom photo.

Matthew McCaugnahey



Taylor Lautner

The Twilight star looks incredibly tanned for his big prom day and it looks like he went with a lot of hair gel for the big day.

Michelle Obama

We are all wondering what President Barack Obama has to say about the First Lady’s gown. That long slit up the thigh is pretty daring!

Kelly Pickler

This is hands down one of the worst from the list. Kelly was channeling her inner belly dancer in 2003 as she poses in a field before her prom. Kelly, what were you thinking?

Claire Danes


Most Popular