Awkward Celebrity Prom Photos That Are Too Amazing Not to Obsess Over

Jennifer Hudson

Jennifer Hudson shared a look back at her 1999 prom photo in a segment on her talk show in May 2024. "I cannot believe that was 25 years ago!" she said, before bringing her friend Walter onstage to recreate the moment.

Ellen DeGeneres

Back in 2020, Ellen DeGeneres sent a positive note on National Prom Day (March 31) to students who missed their prom due to the coronavirus pandemic.

"If your prom was supposed to be this weekend, I wanna see your gorgeous prom outfits. This was mine, so the bar is low," she quipped on Instagram. "Post yours with #ellenprom. I promise you'll wear them to prom soon."

Nick Kroll

In February 2020, comedian Nick Kroll participated in When We All Vote and MTV’s #promchallenge to help students and teachers find creative ways to register voters. "If you'll turn 18 before Election Day, make sure to register to vote now!" he wrote on Facebook.

Michelle Obama

Before there was Barack Obama, there was Michelle Obama's prom date, standing beside her while she sat in a large wicker chair.

"Throwing it back to my 1982 prom night and this pink satin, polka-dotted dress," she captioned the snap on Instagram.

Paul Scheer

Paul Scheer made his prom day extra sweet, pairing a delicious accessory to go with his black tuxedo, colorful bowtie and matching vest.

"Did I rock a Gummi Bear Corsage for my High School prom? You're damn straight I did," the comedian wrote on Instagram with an image of him alongside his prom date.

Tracee Ellis Ross

"18 year old me in 1990 ready for my prom in this @giorgioarmani dress, bangles and shoes," Tracee Ellis Ross captioned a series of throwbacks on Instagram.

One photo shows the Black-ish star wearing a sleek black dress while posing in a living room; the others show the actress posing in the same outfit — this time, in the kitchen amid bright flashing lights.

Kerry Washington

The Scandal actress stopped and smelled the roses on her way to prom — well, one of the proms she attended.

She smugly reminded us in the photo's caption: "I'm throwin' it back…to prom! Well, one of em. I went to a few. Tee hee."

Jimmy Fallon

The comedian poked fun at himself by tweeting a photo of his #awkwardpromstory with the caption: "My date went tanning the night before. I did not. I looked like Powder."

In the picture, the Tonight Show host poses in a black tux alongside his prom date — wearing a pale pink dress — in front of a soft blue backdrop.

Will Ferrell

Will Ferrell wore a tiara to his prom — because of course he would. In the black-and-white photo, the comedian also dons a white dress shirt and black bowtie while posing with his flower-wearing prom date.

Matthew McConaughey

Before all of the Oscars, Matthew McConaughey dressed to the nines for his prom and adorably coordinated his royal blue bow tie with his prom date's dress.

Brad Pitt

If a young Brad Pitt showed up to your doorstep with feathered hair and that charming smile to ask you to prom, how could you say no?

Josh Duhamel

Before the fame and high-profile marriage to Fergie, Josh Duhamel was just a young, dazed teen who rocked a green bowtie and matching cummerbund to his high school prom.

Candace Cameron Bure

The Full House actress took her then-TV boyfriend Scott Weinger (a.k.a Steve) to her real-life senior prom.

*Cue the awwwws from the live studio audience*

John Stamos

Who could resist that hair? John Stamos posted this epic throwback on Instagram, which just goes to show that once a heartthrob, always a heartthrob.

Taylor Swift

The "Anti-Hero" songbird lived out her "normal life" fantasy by participating in MTV's Once Upon a Prom in 2008. She made high school senior Whit Wright the star of the night and revealed that the whole experience was "the coolest thing!"

Halle Berry

All hail the queen! Halle Berry snagged her high school's prom queen crown during her senior year.

Taylor Lautner

Twilight star Taylor Lautner enjoyed his own high school prom experience, complete with a cool striped dress shirt and spiked hair with lots and lots of gel.

Sandra Bullock

The Bird Box actress danced the night away with adorable French braids and ribbons in her hair. So cute!

Bethenny Frankel

Real Housewives of New York City star Bethenny Frankel posted this a-ma-zing throwback on Instagram and asked her followers, "Who else rocked the 80s puff sleeved prom dress look?!"

Tom Brady

This handsome stud posing awkwardly in his living room would later blossom into seven-time Super Bowl champion Tom Brady.

Danielle Fishel and Lance Bass

The Boy Meets World star and *NSYNC singer — who dated for a little over a year as teens — went to prom together and Bass later revealed, "It was terrible!"

Alex Guarnaschelli

Chopped judge Alex Guarnaschelli posted this throwback on Twitter (now known as X) to say, "Prom night baby. #wow #pinkdress #fashionalert."

She killed it with that fabulous perm and powder pink dress.

Meg Ryan

You’ve Got Mail actress Meg Ryan was caught staring into the eyes of her dreamy prom date.

Gwen Stefani

Gwen Stefani posted a sweet throwback on Instagram of herself at 17, wearing a prom dress her mother had made for her. The beautiful gown was inspired by Grace Kelly's dress in the 1954 film Rear Window.

Beyoncé

Before she was one of the biggest names in the entertainment industry, Beyoncé turned heads at prom. Although it's hard to imagine her holding hands with anyone other than her husband, Jay-Z, this rare throwback shows the future superstar posing for a prom pic with her high school sweetheart, Lyndall Locke, in 1998.

Rihanna

Rihanna was every bit a bombshell in this gorgeous royal blue gown complemented with a corsage bracelet. Here, the singer attends prom with a lucky high school student for MTV's Once Upon a Prom special in 2007.

John Krasinski

John Krasinski — decked out in a black suit, white shirt, red tie and yellow boutonnière — shared this gem on Instagram in 2020 to get fans of his Some Good News YouTube series excited for the occasion. "First of all... you’re welcome," he quipped in the caption. "Second of all I can’t take it anymore how much you are all missing your prom. So let’s do something about it!"

Snoop Dogg

To celebrate their anniversary in 2016, Snoop Dogg shared this prom throwback on Instagram of him and his high school love — and now-wife — Shante Broadus. In the caption, the rapper wrote: "19. Years today @bosslady_ent Happy anniversary been a1 from day 1 💝💕🌹🌟🌟🙏🏾 thanks for my kids 💫💝💕🕊🕊"

Tony Goldwyn

The Scandal heartthrob looked quite charming at prom rocking a dapper black-and-white outfit, white boutonnière and noticeably lengthier locks.