Throwback Celebrity Prom Photos That’ll Make You Cringe and Smile

What’s more exciting than watching your favorite celebrities in movies or on social media? Seeing rare and throwback pictures of them at their high school prom! These celebrity prom photos are going viral because they show a totally different side of Hollywood stars. Some pictures are super awkward and funny, while others are so stunning you’ll think they haven’t aged at all.

If you’re a fan of celebrity gossip, prom fashion trends, or love before-and-after transformations, you’ll love these photos. From red carpet royalty to pop icons, these images reveal how far they’ve come—and how relatable they once were!

Britney Spears (1996)

Before she became a global pop music superstar, Britney Spears was just a small-town girl attending Parklane Academy in Mississippi. She had already been part of the Mickey Mouse Club, but this rare prom picture shows her in a more normal teen moment. Fast forward, and Britney became one of the top-earning female artists in music history, with her life making headlines for both fame and personal battles like her well-known conservatorship case.

RuPaul (1983)

This amazing prom photo shows RuPaul, the legendary drag queen and creator of the hit show RuPaul’s Drag Race, way before he became a household name. Dressed with style and confidence, RuPaul went to prom with filmmaker Deborah Kampmeier at Patrick Henry High School in Georgia. It’s easy to see he was a fashion icon in the making and always stood out from the crowd.

Beyonce (1998)

Here’s a rare photo of Beyoncé, the Grammy-winning singer and music industry mogul, at her high school prom in 1998. She attended Alief Elsik High School in Houston, Texas, and was pictured with her first known boyfriend, Lyndall Locke. Their teenage love story is often talked about in interviews and articles, and this throwback shows Beyoncé during her early journey to becoming one of the most powerful female celebrities in the world.

Jennifer Aniston (1987)

Before she became America’s sweetheart as Rachel Green on Friends, Jennifer Aniston went to prom at the Fiorello H. LaGuardia High School of Music & Art in New York. This 1987 photo is a total blast from the past—and we almost didn’t recognize her with that retro hairstyle! Her date remains unknown, but we bet he’s proud to say he took one of Hollywood’s most beloved actresses to prom.

Ellen DeGeneres (1976)

Long before becoming a famous talk show host and LGBTQ+ icon, Ellen DeGeneres attended her prom at Atlanta High School in Texas. In this rare photo, she’s wearing a dress, has long hair, and is pictured with a male date—something fans may find surprising today. Ellen later embraced her true self and became a symbol of courage and authenticity in the entertainment industry.

John Hamm (1989)

Before starring in the hit TV show Mad Men, Jon Hamm attended prom at John Burroughs High School in Missouri in 1989. His date? Actress Sarah Clarke, who later became famous herself. Fun fact: she also dated actor Paul Rudd later on! Despite that early love triangle, Hamm and Clarke remain good friends today. This is a perfect example of celebrity yearbook photos revealing early Hollywood connections.

Jeremy Renner (1989)

That smile hasn’t changed! Marvel star Jeremy Renner, best known for playing Hawkeye and starring in The Hurt Locker, looked adorable at his prom in 1989. He attended Fred C. Beyer High School in Modesto, California. His youthful face and charm were clearly there from the beginning, and this photo shows why he’s still a fan favorite in action movies today.

Amy Poehler (1989)

Long before becoming a comedy queen and star of Parks and Recreation, Amy Poehler was a teen headed to prom at Burlington High School in Massachusetts. She later trained in improv comedy and went on to create a lasting career as an actress, producer, and director. This throwback proves that even future comedy legends have prom night jitters too!

Lizzy Caplan (2000)

Known for her quirky roles in movies like Mean Girls and TV shows like Masters of Sex, Lizzy Caplan stood out at her 2000 prom at Alexander Hamilton High School in Los Angeles. Her wild hairstyle and bold expression make this one of the most unforgettable celebrity prom photos. Bonus points to her date, who matched his tie to her hair color!

Debra Messing (1986)

Before starring in Will & Grace, Debra Messing was a theater-loving teen at East Greenwich High School in Rhode Island. Her prom photo screams 1980s style—from big hair to glam makeup. Even then, her love for performing arts was clear, setting the stage for a successful career in TV and film.

Matthew McConaughey (1989)

The Dallas Buyers Club star and Oscar winner was already turning heads in high school. Matthew McConaughey was voted “Most Handsome” at Longview High School in Texas. A fan once shared this prom photo online, revealing that the girl in the bright blue dress was their aunt! With his charming smile and southern charm, it’s no wonder he grew up to be a top Hollywood heartthrob.

Taylor Swift (2000s)

Before becoming a global pop and country music superstar, Taylor Swift attended Hendersonville High School in Tennessee for just two years. She later moved to Aaron Academy to help balance her school with her rising music career. The prom photo in question is mysterious—fans don’t know if it’s from her own prom or someone else’s. Either way, this is a rare peek at Taylor before she was famous, during her early teenage years.

Gwen Stefani (1987)

Fashion-forward even in high school, Gwen Stefani shared this stunning prom photo on Instagram, showing off a dress she made with her mom. Inspired by Grace Kelly’s 1954 film Rear Window, her prom outfit was elegant and unique—just like her future style as a rock and pop singer. Gwen attended Loara High School in California, and this sweet memory proves her love for DIY fashion and celebrity style started early.

Will Ferrell (1996)

Funny man Will Ferrell might look serious at first glance in this prom photo, but the tiara on his head gives away his goofy side. Known for always making people laugh, he was voted “Best Personality” at University High School in California. Before becoming a comedy legend, he was already cracking jokes at talent shows and school events. This photo captures his early love for making people smile.

Lady Gaga (2003)

Long before her wild outfits and Grammy wins, Lady Gaga was known by her real name: Stefani Joanne Angelina Germanotta. She attended prom at the Convent of the Sacred Heart, an all-girls Catholic school in New York. In this rare photo, she looks like a typical teen, but even then, she considered herself unique. This is one of those celebrity transformation photos that show how far she’s come—from shy student to international pop icon.

Renee Zellweger (1987)

Oscar-winning actress Renée Zellweger, known for Bridget Jones’s Diary and Chicago, went to prom at Katy High School in Texas. In this classic ’80s photo, she’s wearing a stylish black gown and gloves, giving off serious drama. Even in high school, her passion for the arts and strong personality were shining through. Her journey from Texas teen to Hollywood leading lady is truly inspiring.

Harry Styles (2009)

Before he became a global heartthrob and fashion icon, Harry Styles was just a schoolboy attending his formal at Wilmslow High School in Cheshire. While the girl in the photo wasn’t his actual date, he did attend the event with Lydia Cole—who later shared a photo of them together backstage at a One Direction concert. This is a great celebrity throwback showing Harry’s humble beginnings before dominating both the music and fashion world.

Fergie (1993)

Before joining the Black Eyed Peas and becoming a chart-topping solo artist, Fergie (real name: Stacy Ann Ferguson) was a student at Glen A. Wilson High School in California. Her 1993 prom look was soft and feminine, very different from the edgy pop star image we know today. Standing proudly next to her date Vincent Dean Malicek, this is one of those celebrity prom pictures that show the surprising fashion choices stars made back then.

Karlie Kloss (2011)

Before becoming a Victoria’s Secret Angel and one of the top supermodels in the world, Karlie Kloss was a high schooler at Webster Groves High School in Missouri. She attended prom in 2011 with her high school crush, who sadly turned her down as a boyfriend but still went as her date. This sweet story proves that even runway queens can have regular teen experiences.

Kellie Pickler (2004)

Two years before competing on American Idol and launching a successful country music career, Kellie Pickler stunned at North Stanly High School’s prom in a bold red gown. Her stylish look turned heads and possibly even inspired her hit single Red High Heels. Kellie’s prom picture is a perfect example of her trendsetting fashion sense, even before she was in the spotlight.

Meryl Streep (1966)

Long before becoming one of the most awarded actresses in Hollywood, Meryl Streep was already a star at Bernards High School. She was a cheerleader, homecoming queen, student body leader, and even trained as an opera singer. Her prom photo reflects her ambition and confidence, showing she was always destined for the spotlight.

Snooki (2006)

Before becoming a breakout reality TV star on Jersey Shore, Snooki looked like the sweet girl next door at her prom. Dressed in a light blue strapless gown and rocking a deep tan, this photo screams early 2000s style. Fans love her for sharing these hilarious and relatable celebrity throwback photos, showing her wild side wasn’t far behind.

Robin Wright (1981)

Robin Wright, best known for House of Cards and Forrest Gump, attended La Jolla High School in Southern California. Even as a teen, she was modeling and prepping for a career in acting. She landed her first TV role at 18 and grew into one of the most respected actresses in TV and film, with many nominations to her name.

Blake Lively (2005)

Blake Lively looked stunning at her prom during her senior year at Burbank High School. Already acting in The Sisterhood of the Traveling Pants, Blake was balancing school and Hollywood. A cheerleader, class president, and choir member, she truly did it all. This celebrity prom photo shows she’s always had that natural beauty we still see today.

Josh Duhamel (1990)

Before becoming a Hollywood actor and fashion model, Josh Duhamel was just a teenage guy in North Dakota going to prom at Minot High School. His throwback photo shows a memorable haircut and a funny caption where he joked about being stunned that “a real live girl” asked him to prom. This down-to-earth humor is part of what makes him a fan favorite.

Snoop Dogg (1989)

This photo is not just a sweet prom memory—it’s a celebrity love story that lasted. Snoop Dogg, born Calvin Cordozar Broadus Jr., took his high school sweetheart Shante Broadus to prom at Long Beach Polytechnic High School. Years later, they’re still married. He shared this photo on Instagram to celebrate their 19th wedding anniversary. Even with fame and challenges, their love is a reminder that true relationships can last—even in Hollywood.

Brad Pitt (1982)

Brad Pitt looked just like any other high school senior when he attended prom at Kickapoo High School in Missouri. Known today as one of the biggest stars in Hollywood, he was already active in school life, taking part in sports and theater. He went to prom with Tonya Westphalen, who, like everyone else, couldn’t have known that her prom date would become a Hollywood A-lister.

Tyra Banks (1991)

Before becoming a top-paid supermodel and host of America’s Next Top Model, Tyra Banks was often called an “ugly duckling” as a kid. But by age 15, she was modeling and changing the game. This powerful prom photo from Immaculate Heart High School in Los Angeles shows her strong presence even then. Her date is unknown, but all eyes are on Tyra.

Reese Witherspoon (1994)

Reese Witherspoon, star of Legally Blonde and many hit movies, attended prom with her classmates at Harpeth Hall School, an all-girls school in Nashville. She was already a high achiever, with her parents calling her “Little Type A” because she always gave 100%. Her prom photo shows the charm and ambition that later made her a Hollywood powerhouse.

Kim Kardashian (1998)

Before launching a massive media empire, Kim Kardashian attended her prom at Marymount High School with her boyfriend at the time, TJ Jackson, son of Tito Jackson from the Jackson 5. Even though this rare black-and-white photo hides the color, Kim wore a stunning blue dress, and TJ matched his tie to her outfit. It’s one of those celebrity throwback photos that shows her early ties to fame and entertainment royalty.

Jessica Alba (1997)

Even in high school, Jessica Alba had star power. She attended prom at Claremont High School in California with her boyfriend, Chris Lakkees. Although she started acting at just 13, this prom photo shows her as a regular teen enjoying the night. Her youthful glow hasn’t changed, proving why she became a fan favorite in both movies and beauty brands.

Shailene Woodley (2006)

Shailene Woodley, known for Divergent and Big Little Lies, rocked a stunning blue dress at her prom at Simi Valley High School in California. Shared on her Instagram, this photo captures her bold fashion and natural beauty. While we don’t know much about her prom date, we do know that Shailene’s confidence and individuality were already shining through.

Angelina Jolie (1993)

Angelina Jolie, now a global superstar and Oscar-winning actress, went to prom at Moreno High School in California. Known for her rebellious teenage years, she once embraced a full punk style, dressing in all black and going to rock concerts. This prom photo shows a more classic side of her, but as she later said in an interview, she’s still “a punk kid at heart”—just one with tattoos and red carpets now.

John Stamos (1980)

John Stamos, best known for his role on Full House, shared his white-suit prom photo on Instagram—and fans loved it. He graduated from John F. Kennedy High School and was set to attend Cypress College before turning to acting full time. Thanks to early TV roles, his charm and talent quickly made him a household name. This is one of those celebrity prom photos that screams classic 1980s style.

John Krasinski (1997)

Before becoming one of the most influential people in the world, according to Time Magazine, John Krasinski was a high school student at Newton South High School in Massachusetts. His breakout role came in The Office, and he later earned success as a director and producer. This prom photo shows a young man on the edge of stardom—without knowing just how far he’d go.

Danielle Fishel and Lance Bass (1999)

This double-star prom moment features Danielle Fishel, known from Boy Meets World, and Lance Bass, a member of the legendary boy band NSYNC. The couple attended Calabasas High School prom together. Both went on to have big careers in music, television, and film, but this sweet prom picture reminds fans of their early Hollywood beginnings.

Tom Brady (1995)

NFL superstar Tom Brady shared his prom photo from Junipero Serra High School in San Mateo, California, with a fun caption: “Who’s ready for the weekend? This guy is!” Even back then, he played football, baseball, and basketball, but it was football that launched his career. This prom throwback is a look at one of America’s most iconic quarterbacks before the fame and Super Bowl wins.

Kendall Jenner (2012)

Kendall Jenner, a runway model and reality TV star, once shared that she didn’t go to her own prom. But this photo shows her all dressed up at a prom with her then-boyfriend Julian Brooks. Her advice to fans: you won’t regret skipping your prom if it’s not your thing. Still, it’s fun to see this softer side of Kendall, known for her fashion-forward image today.

George Clooney (1978)

Before becoming one of Hollywood’s most charming leading men, George Clooney was a regular student at Augusta High School in Kentucky. He played sports and even tried to go pro in baseball but didn’t make the team. After a short time at the University of Cincinnati, he left college and was later discovered on the TV series ER. This prom photo is a rare glimpse of Clooney as a teen with big dreams.

Nick Cannon (1996)

Nick Cannon, now a well-known TV host, actor, and rapper, didn’t attend his own prom because he graduated early. But that didn’t stop him from getting invited to other schools’ proms. In this photo, he’s seen rocking an all-white tux and matching shoes—truly a bold and stylish look. Even as a teen, Nick had star power and charisma that made him a prom favorite.

Jimmy Fallon (1993)

Late-night host and comedian Jimmy Fallon shared this hilarious throwback prom photo from St. Mary of the Snow High School in New York. Wearing a classic tux and standing next to his very tan date, Fallon joked, “I looked like Powder,” referencing the difference in skin tone. It’s one of the most relatable celebrity prom photos, showing even famous comedians had awkward teen moments.

Tupac Shakur (1996)

This touching story of Tupac Shakur, the legendary rapper and activist, shows a softer side. A fan without a prom date wrote to his team asking him to be her date. To everyone’s surprise, Tupac showed up at her house in a white tux and made her night unforgettable. This moment, captured at John Muir High School, proves that behind the fame, Tupac was a true gentleman.

Demi Lovato (2010)

Before becoming a global pop star and actress, Demi Lovato attended prom at Grapevine High School in Dallas, Texas. This fun and genuine photo shows Demi smiling with their date during a happier time before switching to homeschooling due to a busy acting career and struggles with bullying. A touching reminder of real teen experiences behind the spotlight.

Gigi Hadid (2013)

Supermodel Gigi Hadid looked like any other high schooler at her prom in Malibu High School. Just a few years later, she became International Model of the Year and walked for brands like Chanel and Dior. These sweet prom snapshots show a normal, fun-loving Gigi just before she took over the fashion world.

Elizabeth Banks (1992)

Actress, producer, and director Elizabeth Banks was already turning heads at Pittsfield High School in Massachusetts, where she was crowned Prom Queen in 1992. She started acting in school plays and went on to become one of the most successful women in Hollywood comedy and filmmaking. This rare photo proves she was born for the spotlight.