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Celebrity Yearbook Photos: The Good, the Bad, and the Awkward

High school is known as an awkward time for a reason, whether you’re a chess club scrub or a football hero. It’s the same for the celebrities we’ve spent hours idolizing on TV, in movies, and on the concert stage. Even child stars like Miley Cyrus had struggles under Disney’s thumb. Some hit puberty looking like they were ready for primetime, and others had to settle for outcast status while their talent blossomed. How do we know all this? Lucky for us, many celebrity yearbook photos have made their way online thanks to social media and the “Throwback Thursday” trend of sharing past memories.

Let’s take a trip down memory lame lane and see how ridiculous – or not – our favorite celebrities were in their youth by checking out their high school photos. Which celebrity yearbook photos surprised you the most?

Jennifer Lopez

Jenny was still “on the block” back in 1987 at Preston High School, a Catholic school for girls.

Believe it or not, her short ‘do was fashionable and daring, and fit for the athlete and dancer she was back in the day.


If you look like this in high school, your rap game had better be tight.

Marshall Mathers looked like a potential victim of bullying, and he was. The constant attacks he remembers were likely the source of the ferocity of his rhymes.

Brad Pitt

That “Butt cut” hairstyle screams “future golf pro,” but fortunately for millions of women the world over, Pitt picked acting over a 9-iron.

Angelina Jolie

Born into an acting family (Jon Voight is her father), Jolie was already taking acting lessons at the prestigious Lee Strasburg Theater Institute as a teen.

With her exotic looks, there was no question she would capture the industry’s attention.

Snoop Dogg

Calvin “Snoop Dogg” Broadus spent his high school years rolling with classmates Warren G and the late Nate Dogg — with whom he would later make music — and checking out fellow Long Beach Polytechnic student Cameron Diaz. Diaz told George Lopez she remembered Snoop with braids, but in this high school photo he looks quite wholesome!

Tina Fey

Tina Fey considered herself a “super nerd” in high school, and well, the proof is in the photos.

She was a choir member, tennis player, and honor student. Given how successful she is today, Fey gives hope to nerdy girls everywhere.

George Clooney

Wow, George Clooney’s middle school picture makes him look like a tiny Bond villain.


Queen Bey was already in Destiny’s Child when she was a high school freshman in 1996.

She had “star” written all over her even then.


Like many famous rappers, the Jigga man was already plying his trade in high school.

Jay-Z battled classmate Busta Rhymes and chilled with another classmate, the late Christopher “Notorious B.I.G” Wallace.

When he wasn’t on the corner rhyming, he was on the corner selling dope, as he constantly reminds us.

Jennifer Lawrence

Jennifer Lawrence was a highly motivated student. She made a deal with her parents that she could pursue acting at a young age if she graduated early.

She did, finishing with a 3.9 GPA while being a cheerleader. Cute? Yes. Glamorous, award-winning actress? You’d never think so from her high school photo.

Jerry Seinfeld

In high school, Jerry Seinfeld looked like a character from the film Dazed and Confused, a stoner in the back of the class making jokes. In fact, his friends from Massapequa, NY, say he was a jokester from an early age.

Nicki Minaj

The “Anaconda” singer looked like a typical New York high school student, though a video from her drama class reveals the intensity with which she would pursue stardom.

Blake Lively

The Gossip Girl star had ambition by the pound in high school. She was a cheerleader, a member of the choir, and the senior class president.

Close observers on celebrity blogs suggest she may have had plastic surgery before becoming a television star, though we’ll let you be the judge of that.

Britney Spears

The multi-platinum singer has been performing professionally since childhood. Even in junior high school, her classmates recognized her as a potential starlet. We guess they saw something we wouldn’t see until she broke out on the national stage.

Then again, this was Kentwood, La., population about 2,000 people. There wasn’t much to choose from.


Pharrell Williams and his musical partner, Chad Hugo, were prodigies, and Williams was already a pro in high school.

He got his first writing and production credit right after graduation, on the 1992 song “Rump Shaker.”

He doesn’t appear to have changed much since high school, other than losing his “Gumby” hairstyle.

Taylor Swift

Taylor Swift moved to the Nashville area to pursue a career in country music.

In high school, she was already grooming herself for stardom, so she doesn’t look significantly different then from now. Though she did have the fashion sense of a typical, Abercrombie-shopping Tennessee teen.

Kim Kardashian

While Kim K. may look a bit different now – thanks to the natural process of aging and other less natural factors — elements of her trademark look are still visible in this high school photo.

Kanye West

While his current wife, Kim Kardashian, was a high school freshman, West was absorbing the sounds of 90s rap crews like Souls of Mischief and planning to take over the world through hip-hop.

His emphasis on fashion had already taken hold; his high school classmates voted him “Best Dressed.”

Sean Penn

As a high school student, Sean Penn looked like the surfer-dude character that would make him famous, Jeff Spicoli from Fast Times at Ridgemont High.

He was hardly a stoner, though. He was already interested in film, making movies with his neighborhood friends.


Stacey Ann Ferguson was a big-haired, sweet-looking high school cheerleader, a Girl Scout, and a straight-A student.

She was also a child star, featured on the show Kids Incorporated. At 18, she joined the girl group Wild Orchid and later admitted to going on a sex and drugs binge at the time.

Justin Bieber

Beebs was busy making music and wilding out during his high school years.

He took classes online and earned a degree, telling Martha Stewart during an interview that he finished with a 4.0 GPA. All of his classes must have involved pouting exercises.

Ellen Degeneres

The talk-show host and comic attended her high school prom in a dress that looked made for the old sitcom The Beverly Hillbillies.


Robyn Fenty didn’t graduate high school. She had the talent, ambition, and looks already, winning a beauty pageant while still in school.

Peter Dinklage

The Game of Thrones star sported a new-wave mullet at his Catholic school.

Dinklage was already heavy into acting, having studied drama since the fifth grade. Master your craft early, kids.

Jamie Foxx

In high school, Foxx was Earl Bishop, high school sports star and Jheri curl fan.

The Texan said in an interview with The Tennessean in 2009 that he was already thinking about music back then, sneaking out to see country music stars at a nearby club. He played the piano from an early age, and in high school was a member of a band called Leather and Lace.


Like many female superstars, Madonna was driven to succeed in high school, as well as be in the public eye. She was a cheerleader and a good student, yet she often showed the boys her underwear, according to J. Randy Taraborrelli’s biography Madonna: An Intimate Biography. That sounds about right.

Adrian Grenier

The Entourage star looked like Eddie Munster from The Munsters in high school.

Perhaps the romantic vampire look helped with the ladies.

Bruno Mars

As a high school senior, Bruno Mars looked uptown funky rocking his massive curly Afro. It makes sense, as he was a fan of the Jacksons and Jimi Hendrix as a kid.

Ashton Kutcher

Kutcher may look like a good Midwestern boy in his high school photo, yet he was a ruffian as a young man.

He even broke into his high school in an attempt to steal money, perhaps to pay for a much-needed wardrobe update.

Mila Kunis

Kunis’ future husband, Ashton Kutcher, calmed down and turned himself into a working actor, which enabled the two to meet on the set of That ‘70s Show.

Tom Hanks

The back-to-back Best Actor winner at the Oscars claims he was a painfully shy teenager and a religious evangelical. Hanks did have a great head of hair, though.

Miley Cyrus

Miley Cyrus spent her teenage years in front of the camera and on stage in front of millions.

She worked the Disney good-girl image to death, yet has revealed that she was suffering at the time, struggling with her sexual orientation at 14 years old.

Matt Damon

The son of a schoolteacher, Matt Damon was an introverted student interested in drama.

He acted in several plays but claims he usually lost parts to his classmate, Ben Affleck.

Ben Affleck

Ben Affleck was a child actor; however, he didn’t perform in any memorable series.

While he attended high school with longtime friend Matt Damon, he focused on drama classes and plays. He appeared in an ABC Afterschool Special, Wanted: The Perfect Guy, as Madeline Kahn’s son.


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