Fantastically Awkward Celebrity Prom Photos

Many of us probably hope that our embarrassing prom photos are safely stashed at the back of a drawer somewhere at a relative’s house and are kept far away from public view. Unfortunately for these celebs, their prom pics are out in the open for all of the internet to see (and to poke fun at).

On the other hand, some these stars should be proud to flaunt their teenage selves! Take a look at this gallery to see who totally nailed their prom looks and who might have been better off setting fire to their cringe-y style choices.

So 90s: Danielle Fishel And Lance Bass


Look at these 90s kids! Lance Bass’ frosted tips are on point for the era. In a video blog post for PopSugar, Danielle Fishel (aka Topanga from Boy Meets World) revealed she took Bass of ‘N Sync to her high school prom. The two dated from 1999 to 2000.

In the video, Danielle says Bass initially couldn’t make it because he was going to be in Japan, then she gushes that he sent her, “three dozen roses in the mail with a card that said, ‘Plans have changed, I’ll be in town. Can I take you to prom? Check yes or no.’ And there were two little boxes!”

Next up: he was one of Hollywood’s most eligible bachelors until a couple of years ago… see what he wore to prom!

George Clooney Flashed His Trademark Side Smile

Seth Poppel/Yearbook Library

George Clooney is looking dapper in that massive bow tie and shimmering seventies-style lapels at his senior prom at Augusta High School in 1978. He gives the camera a sexy grin at the dance with his date Laurie Laycock Bach (look at her baby bangs!).

There’s actually a medical reason for Clooney’s sexy side smile: at age 13, Clooney developed Bell’s palsy, a temporary form of facial paralysis. Though his face returned to normal over time, his smile tended to look crooked from the paralysis.

Next: can you guess what RuPaul wore to prom?

RuPaul’s Prom Look Was Epic


There’s nothing awkward about RuPaul Charles’ prom photo aside from the fact that he might be outshining his date. Proving he knew how to put a killer runway-ready outfit together from an early age, RuPaul incorporated glam punk details that are positively stunning from head to toe.

The future drag queen supermodel of the world is positively serving this Siouxsie Sioux-meets-Adam Ant-meets-Jack Skellington look at Atlanta’s Northside High School prom in 1983. RuPaul proudly tweeted a photo of this epic prom pic back in 2014.

What does a future First Lady wear to prom?

Michelle Obama Showed Lots Of Leg


Future First Lady Michelle Obama sits in this amazing throne-like whicker chair like the queen that she is, wearing a fabulous satin gown. Just look at that high-slit skirt showcasing her legs. “I don’t know that I’d let my kids go out with a split that high,” said Michelle on the Ellen show, “So let’s not show this to Malia and Sasha.” She attended prom at Whitney Young High School in Chicago.

Michelle recently recounted her daughter Malia’s prom night in her book Becoming. Taking comfort in the fact that she would have the Secret Service following her, the Obamas let Malia’s date pick her up in his own car. Michelle knew security details “would basically ride the boy’s bumper” all the way to the big dance and back.

Speaking of Ellen…

Ellen Degeneres Is Still In Touch With Her Prom Date

Pinterest/Kristen Philipkoski

“It was a tablecloth at one point,” joked Ellen Degeneres when she revealed her prom photo on her talk show. Ellen rocked this tie-front plaid maxi at her senior prom at Atlanta High School in Atlanta, Texas in 1976.

She’s still in touch with her prom date, Richard, and even hilariously recreated this image by showing up with him dressed in replica outfits on her show! Though today Richard is bald and has lost his hair, his mane back then was total 70s hair goals.

Will Ferrell, Long Before SNL


Will Ferrell: Prom Queen? The future comedy king and Saturday Night Live cast member sports his date’s tiara in his prom photo along with a white shirt and black bow tie. One can only imagine what prom night with Will Ferrell must have been like!

Ferrell almost got a chance to go back to high school in 2014 when a school teacher posted a YouTube video hilariously asking him if he would help chaperone the prom. Though he didn’t make to the dance, the video has over 22,000 views.

This prom queen was also class president

Halle Berry, Beauty And Brains


Before Halle Berry made history as the first woman of color to win Best Actress at the Academy Awards, she was the first black student to be voted prom queen at her mostly-white high school just outside of Cleveland, Ohio.

Berry wore a white off-the-shoulder gown with a ruffled neckline to the Bedford High School prom. Not only was she prom queen in high school, Halle Berry was also a cheerleader, class president, and editor of the school newspaper. She graduated with the class of 1984.

Demi Lovato Attended With A Childhood Friend


Demi Lovato and her date flaunt their fancy ride in this throwback photo from 2010. She wears a cute pink chiffon gown striking this cheeky pose in front of a Rolls Royce. They definitely arrived in style and certainly geared up for a good time!

Lovato attended prom with her childhood friend Nolan. All the way back in kindergarten these two made a pact to go to prom together, and years later Demi made good on her promise! The two attended the Grapevine High School dance in Texas.

Before Making Oscar History, Meryl Streep Went To Prom

Pinterest/Margie Boulé

Before she started collecting all of those Academy Awards, Meryl Streep was voted prom queen in 1967 at Bernards High School in New Jersey. She looks adorable in her tunic dress and tiny tiara, and is working that wind in the hair.

Streep got quite an impressive education under her belt following her high school years. Before making it in Hollywood she went on to get her bachelor’s degree in drama from Vassar College, studied as an exchange student at Dartmouth, and earned her master’s degree from the Yale School of Drama.

Brad And Kim At Kickapoo High School Prom

Pinterest/The Hollywood Gossip

Late 70’s shaggy hair cut: check. Dorky tie: check. Brad Pitt is pictured with his date Kim at Springfield, Missouri’s Kickapoo High School prom.

Brad was quite the overachiever in high school. He was an active student involved in choir, cheerleading, debate club, safety council, and the student council. He participated in many sports including tennis, football, baseball, basketball, wrestling, and diving while managing to make the honor roll all four years of high school. Before being named People Magazine’s “Sexiest Man Alive,” as a teen in school he was voted “Best Dressed”

Courteney Cox Went For The Conservative Look

Pinterest/Cheryl Ochoa

Friends star Courteney Cox looks almost unrecognizable in her prom photo. Could that really be the same girl who danced on stage with Bruce Springsteen in his “Dancing in the Dark” video?

Cox kept things simple and conservative with this button-up dress layered over a dark turtleneck. It looks like her date may have scored a few points with that nice big floral bouquet she’s holding. They attended the prom at Mountain Brook High School in Birmingham, Alabama

Find out whose prom date was arrested for armed robbery…

Fergie Ended Up More Successful Than Her Date

Pinterest/Elle Magazine (US)

Stacy Ferguson (a.k.a. Fergie) was voted junior princess at the senior prom in 1993 at her high school in Hacienda Heights, California. The Black Eye Peas singer stunned in this gown featuring a studded bodice and classy long-sleeved gloves.

Fifteen years later, her prom date Vincent Dean Malicek was convicted of one count armed bank robbery in 2008. While Fergie achieved success in the music industry being G-L-A-M-O-R-O-U-S, a surveillance camera caught her old date robbing a Wells Fargo bank in Santa Ana with a silver handgun.

Brandy Felt Like ‘A Normal Teenager’ At Prom With Kobe


Singer Brandy met a pre-NBA superstar Kobe Bryant at the 1996 Essence Awards. At the time Kobe was just a 17-year-old high school basketball prodigy–and a big fan of Brandy’s. After meeting at the event, Bryant got the courage to ask her to his high school prom in Philly.

Obviously, Brandy said yes and wore a lovely shiny satin Moschino gown. On prom night, Kobe reportedly treated Brandy like a queen and the Moesha starlet got to feel like “a normal 17-year-old” for once. No embarrassing prom photo here!

Jimmy Fallon Says He Looked Like The Character ‘Powder’ At His Prom


Jimmy Fallon tweeted this photo of him and his prom date in 2013 saying, “My date went tanning the night before. I did not. I looked like Powder. #awkwardpromstory” He even tweeted it again in 2017: “My date didn’t tell me she was getting a tan and high heels for the prom. Standing next to her I looked so pale and so small,” he tweeted.

Though he does resemble Casper, his date has the quintessential 80s prom look going on with those white tights and puffy sleeves. And that blue velour backdrop? Most classy.

Uncle Jesse’s Hair Looked Spectacular


That stellar hair, cream tux, ruffled puffy shirt with red trim, and oversized matching cream bowtie John Stamos is wearing in this photo are quite amazing. Garish, but amazing. The lucky girl who got to attend prom with the future Uncle Jesse is sporting some pretty great hair, too. They attended John F. Kennedy High School in Orange County, California.

John Stamos, hair still as spectacular as ever, shared this gem on Instagram in 2015. Stamos wrote, “#TBT #Prom #Hair.” Enough said.

Bravo, Bethenny Frankel


There’s no questioning what decade this Bravo-lebrity attended prom in. Bethenny Frankel’s prom outfit is 100 percent eighties complete with giant puffy sleeves, shaggy bangs, and big curly hair. She paired her long crimson dress with a white floral corsage and dark eyeliner to complete the look.

Before she was a Real Housewife and Skinny Girl mogul living it up in New York City, Frankel attended Wheatley High School’s prom on New York’s Long Island in 1984.

Gwen Stefani

Instagram/Gwen Stefani

Style icon, designer, and singer Gwen Stefani shared this photo of her on prom night via Instagram. She and her mom made this unique prom dress when she was just 17.

The dress and accessories were inspired by Grace Kelly’s outfit in the classic Alfred Hitchcock film Rear Window. Complete with a similar 60s hairdo, Stefani is actually a dead ringer for Princess Grace here! She attended Loara High School in Anaheim, California and graduated with the class of 1987.

Jessica Alba Wore A Romantic Look For Prom


If you look past the oddly-posed elbow cupping and her date’s super awkward smile, teenage Jessica Alba looks beautiful in this romantic Shakespearian-esque dress she wore to her prom. Her outfit complements the rose arrangements at the forefront of the prom photo.

According to TMZ, she and her prom date, Chris, dated on-and-off throughout high school. Interestingly enough, his relationship with Alba inspired him to create a website designed to help couples prevent unnecessary break-ups.

Bruno Mars’ Hawaiian Prom Night


This series of prom photos is adorable. Bruno Mars, then known as Peter Hernandez, attended prom at President Theodore Roosevelt High School in Honolulu, Hawaii, sporting a funky fresh afro hairdo. The “24K Magic” singer even matched his lei to his date’s purple ensemble!

Mars is one of the best-selling recording artists of all time and started performing at a very young age. At only four years old, he was known as the youngest ever Elvis impersonator. Looks like he’s been stylish his entire life.

What does a future American Idol winner wear to prom?

Kellie Pickler Bared Her Midriff With This Ensemble


Every dad in America who has a teenage girl is probably gasping in horror right now. American Idol contestant Kellie Pickler wore this, um, interesting hot pink two-piece to the prom. How did her parents let their little girl out of the house in a maxi shirt and bra?

It’s very similar to Christina Aguilera’s “Genie in a Bottle” music video look. Perhaps Pickler’s high school didn’t have a strict dress code. She’s wearing this with confidence and even rocking a sparkly belly piercing, proving it’s not what you wear, it’s how you carry yourself!