30 Awkward Celebrity Prom Photos From The Past (2024)

30 Awkward Celebrity Prom Photos From The Past (1)

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Before popular celebrities graced events such as the Met Gala, Oscars, or Grammys with their designer looks they attended the less coveted "red carpet" event of prom. Yes, stars they're just like us, and the proof is in these gloriously awkward photos of our favorite famous people dressed to impress this celebrated high-school tradition.

On this list, you'll find some pretty staggering transformations from cringy to glamorous, whereas other lucky ducks were fortunate enough to avoid their awkward phase and look as if they haven't aged a day. Scroll down below to find your favorite celebrity's prom photos and don't forget to vote!

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#1

Jeremy Renner

30 Awkward Celebrity Prom Photos From The Past (2)

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Vanessa Galvan

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Oh, that mullet! :D

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Prom night is now synonymous with the high-school experience but the first recorded prom in history took place at Amherst College where male students invited female students from Smith College to dine and dance back in 1894. The dance evolved into a high-school tradition in the 1900s and was nationwide by the 1930s.

#2

Ru Paul

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Emir

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Still looks fierce.

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#3

Barack Obama

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KT Trondsen

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Did he have two dates? lol

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One of the traditional etiquettes of prom is for the boy to give the girl a bundle of flowers called a corsage for her wrist or to be pinned to the top of her dress. In the past, the corsage was placed on the hip. The term “corsage” actually means “bodice” which dates back to the 19th century with French origins, so the former positioning makes more sense.

#4

Will Ferrell

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Even a goofball nack then ;)

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#5

Meryl Streep

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Kaisu

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Meryl has always had and still has this really gorgeous natural beauty

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Most celebrities had their prom experience before fame, but that was before the trend of doing a celebrity prom was born. In 1963, President Kennedy was not invited but unintentionally crashed the prom of John Burroughs High School. The politician scheduled a $1,000-a-plate fundraiser in the largest room at the Beverly Hilton Hotel but as it turns out, the students had already booked the same room two years prior. JFK gave up the larger room to the students and settled for a slightly smaller one for his event. In an act of goodwill, he stopped by to say hello to the teens accompanied by comedian Jack Benny.

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#6

Angelina Jolie

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rai mei

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she has always been gorgeous

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#7

Terry Crews

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Sleep Meister

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He ate his date and evolved into the tank he is now.

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While the average high-schooler may have to settle for a decked out gymnasium for their annual prom, the wealthier schools (where celebrities attend) might get glitzier options. In 1975, Susan Ford, the daughter of President Gerald Ford, got permission to throw her prom in the White House. The President was away in Europe at the time so the dance was chaperoned by the Secret Service.

#8

Ellen Degeneres

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Sreejith

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4 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017
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age in reverse gear

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#9

Lady Gaga

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Janine B.

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Still beautiful.

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One can only imagine the amount of money celebrity teens are dishing out for prom but even for the average American, the costs can be outrageous. When you add up the tickets, dress cost, tux rental, limos, and other common prom expenses, parents have paid an average of around $900 for their high-schoolers to attend these events. In 2013, the average peaked at $1,139 - those are some red carpet numbers.

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Heather Brady-Connor

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4 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017
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I don't think she ages. :)

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#11

Jimmy Fallon

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Moriarty2

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From that angle it looks like he took Michael Cera in a wig to prom.

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#12

Jennifer Aniston

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Cuitlahuac Guerra

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Is that dude chip mattews? Ross is so sad :(

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#13

Jessica Alba

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Ruby

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Look how happy that guy is. He can't believe his luck.

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#14

Matthew Mcconaughey

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htbq

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alright

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#15

Bruce Willis

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rai mei

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Can't believe it's Bruce Willis

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#16

Brad Pitt

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Alusair Alustriel

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4 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017
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I like him more as an older guy than a teen. Same happens with Harrison Ford, he looks bext from his 30-ties up for me :D

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#17

Robin Wright

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Monty Is Fiennes

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Gorgeous woman...

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#18

Taylor Swift

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Elisabeth Bergbom

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She was really pretty back then, and obviously she still is

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#19

Reese Witherspoon

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Luis Milian

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she still as beautiful as ever

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#20

George Clooney

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"Someday, I'm gonna be famous, and then I'll provide the barks for a cartoon dog, and my life will be complete. Marry a hot lawyer? That might come second to the cartoon dog."

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#21

Rihanna

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Valentina Lattante

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no one is supposed to look that good in high school!

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#22

Michelle Obama

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Emir

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Lookin like a queen.

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#23

Beyoncé

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Tor Rolf Strøm

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Is that Carlton?

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#24

Scarlett Johansson

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Michael Naegele

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she was always a hot lady. WoW

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#25

Ashton Kutcher

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QueenOlive

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What are you guys talking about that's Kevin Malone.

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#26

Natalie Portman

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Jarno Flinkers

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Absolutely stunning.

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#27

Amy Poehler

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Agnes Jekyll

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Awesome. This is true Boston Suburb grad.

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#28

Blake Lively

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Monty Is Fiennes

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No touch hands...

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#29

Courteney Cox

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wasnt she like, super fat at her prom? (just kidding)

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#30

Shane Dawson

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Michka Shoitan

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4 years ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017
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He is the biggest Youtuber and he is famous for changing the Youtube platform with his docu-series and won creator of the year at The Streamys last year and NO, he DID NOT molest his cat, that was a JOKE he made on a podcast.

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30 Awkward Celebrity Prom Photos From The Past (71)

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Hans

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This series as as US american as it gets. The importance of proms is striking...

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Wanda Queen

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it's not all that important to everyone, trust me Hans ;) it's like most everything, if you were a popular person you probably enjoyed it and went to a few, if you were an average jo or joanne you maybe just went once to see what it was like and then got on with your life.

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Jace

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What a stupid title. There’s nothing awkward about most of the images I looked at here. I got sick of seeing photos of perfectly fine looking young people, while under the article’s supposed theme of them being “awkward”. If you’re going to come up with a theme, stick to the damned thing. This is a problem with many of these lists.

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Kenny Kulbiski

Kenny Kulbiski

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As usual I've never heard of at least half of these people. I'm beginning to think maybe I'm the only non celebrity left in America. Which would, of course, make me a ..........celebrity .

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Wanda Queen

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Kenny IS....(dun dun DUN) the last man standing!

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Hans

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This series as as US american as it gets. The importance of proms is striking...

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Wanda Queen

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it's not all that important to everyone, trust me Hans ;) it's like most everything, if you were a popular person you probably enjoyed it and went to a few, if you were an average jo or joanne you maybe just went once to see what it was like and then got on with your life.

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Jace

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What a stupid title. There’s nothing awkward about most of the images I looked at here. I got sick of seeing photos of perfectly fine looking young people, while under the article’s supposed theme of them being “awkward”. If you’re going to come up with a theme, stick to the damned thing. This is a problem with many of these lists.

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Kenny Kulbiski

Kenny Kulbiski

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As usual I've never heard of at least half of these people. I'm beginning to think maybe I'm the only non celebrity left in America. Which would, of course, make me a ..........celebrity .

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Wanda Queen

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Kenny IS....(dun dun DUN) the last man standing!

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