Kim Kardashian

Kim Kardashian is possibly the most successful socialite in human history, parlaying a sex tape scandal into a multi-million dollar fashion and reality TV empire. In the past decade, she was married to hip hop legend Kanye West (with whom she has several children) and even dated SNL breakout star Pete Davidson.

But even back in the day, the well-heeled Kim K had her sights on dating the stars. Recognise her prom date? It’s TJ Jackson, aka Michael Jackson’s nephew and star of short-lived Jacksons successor 3T! What can we say? She has a thing for musicians.

Jimmy Fallon

Jimmy Fallon has a reputation as a bit of a man-child, goofing around on The Tonight Show. But his slick showbiz schtick wasn’t developed overnight – he had to go through the same embarrassing prom pics as everyone else.

“The night before, my companion got a tan at the tanning salon. I did not. I looked like Powder. #awkwardpromstory,” Fallon once tweeted.

Matthew McConaughey

Academy Award-winner Matthew McConnaughey seems like he’s always been in his 40s, even if he’s in his 50s today. But, believe it or not, there was a time when young Matthew nervously took a date to the prom.

We aren’t sure why there’s a moon and star behind them, though. Did he go to prom in Turkey?

Bruno Mars

In many ways, it feels like Bruno Mars was born in the wrong era. Despite being one of the most successful pop stars in recent memory, a lot of his music seems to pay homage to bygone eras, particularly from decades such as the ’70s, ’80s, and ’90s.

The man behind hits such as “Uptown Funk” and “Just the Way You Are” enjoyed himself at his very own prom and didn’t stop himself from rocking some truly impressive Jheri curls!

Ellen DeGeneres

It wouldn’t be until the late 90s that small-screen star Ellen DeGeneres would make history, coming out as lesbian during an episode of her eponymous TV show. Back in the 70s, she looked a little nonplussed with her prom date – or maybe she just wasn’t thrilled with her floor-length, tartan number.

How do we know it was the 70s? Just look at all that beige!

Angelina Jolie

Years before she had a high-profile marriage to Hollywood hunk Brad Pitt, Angelina Jolie was a high school student at Moreno High School, where she was regarded as a “punk outsider.”

The daughter of screen star Jon Voight, though she had little contact with him during her childhood, Jolie was known for collecting knives, and few would have pegged her as the future beauty queen of Hollywood. Never judge a book by its cover!

Rihanna

Rihanna released her debut album at 17, had an international breakthrough at 19, and has since become one of the bestselling artists on the planet, as well as a leading fashion designer and political activist for her home country of Barbados. She was declared a national hero of the island nation in 2021, meaning her full title is in fact “the Right Excellent” Rihanna!

So why is it that her slacker prom date, with his curtain haircut, is acting like he’s the centre of attention?

Gwen Stefani

Gwen Stefani, who’d go on to acclaim with band No Doubt, collaborated with her mother on the construction of her prom dress, which was modeled after the gown worn by Grace Kelly in Alfred Hitchcock’s Rear Window.

Aiming to be Grace Kelly, the future Princess of Monaco, is a pretty high bar to set yourself. But if anyone can pass for being a Rich Girl, it’s Stefani!

Will Ferrell

Once a prankster, always a prankster! SNL and Elf star Will Ferrell had something of the Ryan Reynolds about him back in his high school days, but always had that cheeky edge to his personality.

Let’s be honest, some prom photos are so generic that they’re easily forgotten. Steal your date’s tiara, however, and you’ve got a memory that’ll last forever – and, if the headpiece was worth a pretty penny, you’ve got a down-payment on a box room in New York City!

Meghan Markle

At the age of 17, Meghan Markle was crowned the prom queen, long before she realized that she would one day become a member of the royal family of the United Kingdom. Her senior prom was held in the year 1998 at Immaculate Heart High School, which the now Duchess of Sussex attended in the city of Los Angeles.

As can be seen in the photo taken from the evening, Meghan Markle wore a tiara, a long ball gown, and silver jewelry, all of which gave her the appearance of a member of the royal family. It’s unlikely that her prom date had any idea who the person standing next to him at the time would turn out to be in the future.

Harry Styles

Before he became one of the most famous singers in the world with X Factor composite creation One Direction, and even more famous in his solo career, Harry Styles was a regular guy who worked at a fish and chip shop and went to school in Cheshire. Nowadays, Styles wouldn’t be seen dead having his picture taken in a car park, next to some double yellow lines.

As for his prom date… don’t worry, darling – you’ll find your beau someday!

Taylor Swift

Taylor Swift is the person who is best known for the fact that she has had a number of different guys in her life at the same time. Therefore, it should not come as a surprise that she took a date to the prom at the conclusion of her senior year of high school.

When it came time for Taylor to attend her prom, the young woman, who had not yet garnered a variety of honors and distinctions, went all out in terms of her appearance. In point of fact, Taylor Swift donned a white dress, while her boyfriend wore a spotless white suit and tie to the event.

Britney Spears

She was the southern belle that rose to fame after her hit debut single, “Hit Me Baby, One More Time,” but Britney Spears has never forgotten her roots. While she had already starred in The Mickey Mouse Club alongside many other famous faces, the pop princess made it to her Freshman formal dance, looking ever so glamorous.

She has since gone on to have many number one hits, sell millions of records, and even have her own residency in Las Vegas.

Brad Pitt

He has been voted as the most attractive man in the world in many media reports, and even as a high school student, Brad Pitt was sure to charm you with just his smile. Although sporting a different hairstyle to what most are used to for the actor, Brad Pitt was just another regular high school student back in the day, accompanying a lovely lady to their school prom.

In fact, this picture could be mistaken for a wedding photo with Pitt’s date dressed in a long, white, bridal-looking gown.

Tiger Woods

In an accounting study group at high school, Tiger Woods met his first love, Diana Parr. “I would have been 17, and he was 16—he’s three months younger than me. So he was a junior, and I was a senior,” Parr recalled of their first dinner and a movie date.

It must have been a successful first date since they accompanied one another to prom in 1993. “We were first boyfriend and girlfriend in all sense of the word,” Gravell explained. “We were in teenage love.”

Jennifer Aniston

Jennifer Aniston has spoken about how much she hated the “Rachel cut” during her time on Friends, but we wonder what she thought when she looked back at her haircut during her high school days. The talented actress has always been a beauty, so not even a poor haircut could dampen her looks.

After all, she did win over one of the most attractive men in the world when she married Brad Pitt and didn’t do too bad when she started dating Justin Theroux.

George Clooney

Often lauded as one of the sexiest men on the planet, George Clooney shocked the world when he announced the end of his bachelor days, marrying human rights lawyer Amal Alamuddin in 2014. Back in his days at Augusta High School, however, he definitely had the aura of a future stud!

Clooney hit the A-list with his role as Dr. Doug Ross on the television show ER, which was followed by movies such as Ocean’s Eleven and The American. During his time at high school, George participated in both baseball and basketball, and he even made an attempt to play baseball professionally with the Cincinnati Reds in the year 1977.

Julia Roberts

What we wouldn’t give to have taken Julia Roberts to the prom! What a story that would be to tell the kids, even if Roberts would go on to the bright lights of Hollywood and relationships with Liam Neeson and Kiefer Sutherland.

Roberts discussed this photo on Jimmy Kimmel, noting that her bouffant isn’t actually as huge as it first appears – it’s actually a shadow being cast on the wall!

Jon Hamm

Sarah Clarke was Jon Hamm’s date to his high school prom when he was starring in the show Mad Men. In addition to her subsequent roles as Nina Myers on 24 and Bella Swan’s alternate in Twilight, Clarke went on to date and marry actor Paul Rudd. In point of fact, Hamm and Rudd competed for Clarke’s affections, and despite the fact that Hamm took Clarke to the prom, it appears that Rudd ultimately won her over.

It would appear that the performers have put all of this drama in the past and have continued to be good friends in the years since.

Jessica Alba

It’s hard to believe that fresh-faced Jessica Alba is now in her 40s, but it’s true! It was way back in the late 90s that Alba went to prom. Impressing with her looks and precociousness, she’d already starred in several episodes of Beverly Hills 90210 and scored a recurring role in Flipper.

It wouldn’t be until 2003 that Alba would make her Hollywood breakthrough with the dance movie Honey. Maybe she picked up those moves at her high school prom?

Scarlett Johansson & Jack Antonoff

Scarlett Johansson has been famous since she was a child, scoring a lead role in Home Alone 3 and other family movies, before her career took a more sultry turn as Marvel’s Black Widow. Nowadays, she’s considered one of the sexiest women in the world. But did you know that she used to date musician and songwriter Jack Antonoff?

They ultimately went their separate ways, with Johansson marrying Ryan Reynolds for a time, and now being wedded to SNL anchor Colin Jost. As for Antonoff, he’s currently engaged to Margaret Qualley, the daughter of screen legend Andie MacDowell.

Claire Danes

Initially, the Baz Luhrmann adaptation of Romeo & Juliet was set to star Natalie Portman – but everyone involved was concerned that romance scenes between the young Portman and the older DiCaprio (historically accurate as it might have been) made it look like the future Titanic star “was molesting her.” Danes would be cast in her place, giving her a breakthrough role that made her one of the most recognisable faces on the planet.

Did a high-school age Danes realise her future would be in Hollywood? The answer is yes – she’d already won a Golden Globe for My So-Called Life!

Courteney Cox

This picture was taken in 1980, though the styles on show and the black-and-white style make it look like it could have come out of the early 70s, or even earlier. In fact, the only things that give it away are Courteney Cox’s iconic bright eyes and starlight smile.

The future Friends star used to sport a more demure hairstyle and dowdy coat, but doesn’t she look happy? And with such a bouquet of flowers from her prom beau, why shouldn’t she?

Sandra Bullock

It’s hard to believe that Hollywood icon Sandra Bullock is now pushing 60, given that she looks just the same as she does here, in her high school prom photo! Far from the awkward posing that often comes with these occasions, this candid shot shows Bullock having a great time on the dancefloor.

It wouldn’t be long after graduating that she’d gain early notoriety for rom-coms before earning a spot on the Hollywood A-list in the Sylvester Stallone action movie Demolition Man.

Demi Lovato

Another Disney star on the list! Demi Lovato kicked off their career as an actor, but has since become a multi-platinum-selling recording artist. While there have been speedbumps along the way, it’s Lovato’s pugnacious attitude and emotional honesty that has made them a star.

That’s right on show in this bombastic prom photo. Hey, if you’re going to prom in a fancy car, better make the most of the experience!

Meryl Streep

She’s the leading lady that has been nominated for a staggering 21 Academy Awards, winning three, and 31 Golden Globes, winning eight. With more nominations than any other performer, it is safe to say that Meryl Streep is recognized for her impressive work in the entertainment industry and, after watching her performances, her talent cannot be denied.

Back in the day, she attended Bernards High School, where she became a cheerleader and was chosen as the homecoming queen in her senior year. In spite of such accolades, Streep was nonetheless initially dismissed by legendary Hollywood producer Dino de Laurentiis as a “bruta” [‘ugly thing’]!

Amy Poehler

She is best known for starring as Leslie Knope in the NBC sitcom Parks and Recreation and received a star on the Hollywood Walk of Fame for her contributions in television in 2015. However, before getting her big break on Saturday Night Live, Amy Poehler was a student at Burlington High School.

After graduating in 1989, she attended Boston College, where she studied media and communications, and later moved to Chicago where she met her future co-star, Tina Fey, while studying improv at Second City.

Natalie Portman

Portman attended her high school prom before graduating from Syosset High School in Long Island in 1999. She went on to study ballet and modern dance at the American Theater Dance Workshop in New Hyde Park, New York, which came in handy for her later role in the box-office hit, The Black Swan.

While she has gone to achieve worldwide success, Portman is a Harvard graduate and, in 2002, said, “I don’t care if [college] ruins my career. I’d rather be smart than a movie star.” Fortunately, she is both!

Tupac Shakur

While the late Tupac Shakur will always be remembered for being one of the most important figures in the gangster rap genre, the talented rapper always had a good side to him, which can be traced back to his high school days. He took one of his good friends, Heather, to prom.

The two spent a lot of time together at Baltimore School for the Arts and their prom was at The Belvedere Hotel. Although things started awkwardly, they ended up having a great time.

Elizabeth Banks

Back in the day, Elizabeth Banks was crowned queen at her senior dance and since then, she has never looked back. Casual moviegoers started to take notice of Banks’ raw talent through her work in classic comedies such as The 40-Year-Old Virgin and Role Models.

There is no denying though that her role as Effie Trinket in The Hunger Games took her career to a whole new level. These days, she is directing movies such as Pitch Perfect 2 and Charlie’s Angels.

Meg Ryan

For many, Meg Ryan is undoubtedly the queen of romantic comedies. She had a truly incredible run with movies such as Sleepless in Seattle, When Harry Met Sally and You’ve Got Mail. However, every Hollywood star has to start somewhere and it seems like Ryan was able to channel her romantic vibes way back in high school.

This photo shows her dreamingly staring into the eyes of her date at the prom. Unfortunately, he appears to be thinking about the horrors of the Vietnam War.

Jeremy Renner

Jeremy Renner has come a long way since his prom days. Just recently, he starred as Hawkeye in the highest-grossing movie of all time – Avengers: Endgame.

We never thought we would see an actor like Renner sport such a cheesy-looking mullet! Of course, this hairstyle is synonymous with the ’80s, so it doesn’t take a rocket scientist to work out when this photo was taken…

Halle Berry

It should come as no surprise that Halle Berry was crowned queen at her high school prom during her senior year. The talented actress has had an incredible career, having started off in smaller movies like Spike Lee’s Jungle Fever before ending up in X-Men movies and the James Bond movie Die Another Day.

She truly is the star who does not age. At 53 years old, Halle Berry seems to have been fixed in time ever since her prom days.

Faith Hill

While Faith Hill and Tim McGraw are one of the most beloved celebrity couples in the world, there was a time when the talented country singers weren’t joined at the hip.

Faith wasn’t seeing Tim around the time of her high school prom and she ended up taking someone else with her to her big night. Another celebrity who hasn’t really aged over the years, Faith brought a real touch of class to her prom with her long dress and radiant smile.

Terry Crews

It feels like an eternity since former professional football player Terry Crews burst onto the acting scene with his hilarious role in the movie White Chicks.

His “a thousand miles” rendition has become one of the most used memes of all time and these days, he is enjoying working with the likes of Andy Samberg on Brooklyn Nine-Nine. This didn’t stop Terry though from posting this photo of him and his prom date from back in the day.

Taylor Lautner

To be fair, Taylor Lautner is still pretty young and has plenty of time to prove himself as an actor. His career has hit a bit of dead-end and his Twilight contemporaries Robert Pattinson and Kristen Stewart, in contrast, have managed to build respectable careers for themselves.

However, time is still on Lautner’s side and this photo is a reminder of how much he hasn’t changed over the years. These days, he uses a little less hair gel than he did on prom night.

John Krasinski

John Krasinski is another star on this list who started off with a minor role before building his reputation as a heavily sought-after actor and filmmaker. While he is probably best known for his role in The Office, many believe that he is on his way to becoming a legendary director after making the highly successful horror movie A Quiet Place.

Back in the day though, Krasinski was on the periphery of the many social groups at high school and considered himself as one of the misfits.

Snoop Dogg

It is well known amongst celebrity aficionados that Snoop Dogg went to the same high school as Cameron Diaz. However, it might have been a stretch to think that two would have gone to the prom together.

The rapper responsible for hits such as “Drop it Like it’s Hot” and “What’s My Name?” can be seen posing rather seriously with his prom date. While he hasn’t always been that respectful to women in his lyrics, Snoop was reportedly a perfect gentleman that evening.

Ashton Kutcher

Known not to be taken too seriously, it is no surprise that Ashton Kutcher was front and center busting out the moves during his prom. However, his time in school was not so smooth sailing.

After his family moved to Homestead, Iowa, Kutcher attended Clear Creek Amana High School and, during his senior year, the actor broke into his high school at midnight in an attempt to steal money with his cousin. He was arrested leaving the scene and convicted of third-degree burglary.

Carrie Underwood

Carrie Underwood’s victory on the fourth season of American Idol in 2005 propelled her to the forefront of the music industry, but before to that, she had delayed beginning a career in singing for several years. The native of Oklahoma went to Checotah High School, where she was a member of the Honor Society, a cheerleader, and played basketball and softball.

However, she claimed that after high school she “very much gave up on the ambition of singing.” My life had progressed to the point where it was time for me to stop being idealistic and start making plans for my future in the “real world.”

Lizzy Caplan

Elizabeth Caplan garnered wide attention after starring in Mean Girls, where she played the role of high school outsider, Janis Ian. Meanwhile, Elizabeth, who goes by the name of Lizzy, attended Alexander Hamilton High School and, as seen in her prom photo, she had her own unique style.

Along with the guy in the photo, the actress and her pal co-ordinated their hair color and he went for an unconventional choice of a cow printed jacket. We wonder what they think about this look when looking back at photos.

Reese Witherspoon

Reese Witherspoon looks as though she has not aged a single bit since her photo was taken the night of her high school prom. The Big Little Lies star looked the spitting image of her eldest child and daughter, Ava, while she attended the all-girls Harpeth Hall School in Nashville, during which time she was a cheerleader.

Meanwhile, she was described as a “multi-achiever” and her parents nicknamed her “Little Type A.” Witherspoon went on to achieve even greater things when she pursued acting and is a recipient of many awards.

Debra Messing

Debra Messing recently reprised her role of Grace Adler in the hit sitcom Will & Grace, pleasing her fans around the world. However, before she was even familiar with the character of Grace, she was a student at East Greenwich High School and starred in her school productions of Annie and Grease.

It seems that Messing knew she wanted to pursue acting from an early age, and it has paid off with the actress going on to earn five Primetime Emmy Award nominations, winning once in 2003.

Brandy

Due to the fact that she became famous for portraying the title role in the television series Moesha, Brandy had very little opportunity to participate in things that most teenagers her age would enjoy. Therefore, when Kobe Bryant, who was relatively unknown at the time, invited Brandy to go to the prom with him, she enthusiastically accepted the invitation.

It was said that Bryant had flown Brandy and her mother up to Philadelphia for the dance. Brandy was quoted as saying later, “I simply felt like a normal 17-year-old… I was desperate to have that experience, and if Kobe hadn’t asked me, I never would have gotten it.

Blake Lively

She is now married to Ryan Reynolds, making them one of Hollywood’s most beautiful couples, but Blake Lively undoubtedly caught the eye of many during her high school days. The Gossip Girl star looked radiant in her prom photo, dressed like a real princess.

With her sparkly dress and shining tiara, we are sure her date would have treated her like royalty during their time at prom. Just look at her smile! She was ready to take on Hollywood in style.

Beyonce

Beyonce, often known as Queen B, is so famous that if you haven’t heard of her, you must be living on another planet. Beyonce wed Jay-Z, the man she considers to be her true love, and the couple has now become parents to three children together. Nevertheless, back when Beyonce was just a high school student, she went to her prom with the boy who would become her future husband.

It is safe to say that this relationship was not meant to endure because of her songs that were published several years after her prom, despite the fact that she looked absolutely stunning on that day.

Danielle Fishel & Lance Bass

This one’s a two-fer! That’s right: Girl Meets World star Danielle Fischel really did have NSYNC’s Lance Bass as a prom date.

They both look as gorgeous as ever, but we still can’t forgive that 90s trend of frosted tips. Why did anyone ever want their hair to be described the same way as sugary breakfast cereal?

John Stamos

That’s so 80s! Full House star John Stamos was sporting the long hair before he was on TV, and he’s really put the effort into his prom night – just look at the coordinating flowers, corsage and lilac dress!

The only thing we aren’t really sure on is his decision to wear white gloves. Suddenly he turns from prince charming into a butler quietly removing someone from the party. They look happy enough, at least!

Josh Duhamel

Actor Josh Duhamel was very much into emerald green at his high school prom. Check out that matching bow tie and cummerbund! Very sophisticated, Mister Duhamel!

You can see the beginnings of that chiselled, Hollywood look even in this picture – but it’d be nearly two decades until he married Black Eyed Peas showstopper Fergie!

Taraji P. Henson

Taraji P Henson, the star of Empire, Hidden Figures and Boston Legal, doesn’t have anything to be embarrassed about. Sure, the exaggerated tool on the shoulders is a little much, but it was the 80s. Plus, there’s a twist…

Henson created her dress herself! Turns out she’s not just a stellar actor, but something of a fashion designer, too.

Tom Brady

Did you ever wonder in high school what the rest of your cohort would get up to in life? Even if you picked the high school jock to get a big break in professional sports, you probably wouldn’t predict that they’d become the single most successful quarterback of all time, still winning Super Bowls in his 40s.

Then again, you can detect a real confidence in this prom pic of future Patriot Tom Brady – even if there is a little bit of Biff Tannen about him!

Gigi Hadid

Even supermodels have to start somewhere! Gigi Hadid shared this very 2013-style collage of her high school prom and, amazingly, she doesn’t seem all this different from her friends!

It just goes to show that being a model isn’t necessarily about being the most beautiful person in the world by far – it’s about how you carry yourself. And how many goofy poses you can strike!

Paris Jackson

Paris Jackson, the daughter of the King of Pop and a successful model and actor in her own right, had a pretty fun prom in this teal number.

“Only a loyal friend” would dye their hair simply to match their prom date’s outfit, she added on Instagram. They look great!

Amandla Stenberg & Jaden Smith