Before they were household names, some of Hollywood’s biggest stars were just regular teens navigating cafeteria drama, math homework, and early ambitions—often alongside someone who would also become famous. From future Oscar winners to chart-topping musicians, these celebrity classmates crossed paths long before fame found them, creating unlikely high-school pairings that make their success stories even more fascinating. Here are 20 stars who once shared the same school halls with another major celebrity.
Ben Affleck and Matt Damon
The Hollywood friendship that launched a thousand scripts started in the halls of Cambridge Rindge and Latin School in Massachusetts. The lifelong friends didn’t just attend the same high school; they collaborated on early acting projects and eventually co-wrote and starred in Good Will Hunting, which earned them an Academy Award for Best Original Screenplay. They remain close friends and frequent collaborators in the film industry.
Adam Levine and Jonah Hill
These two stars have a history that dates all the way back to Brentwood High School in Los Angeles, where they were childhood best friends. The Maroon 5 frontman and the Oscar-nominated actor grew up together, and Jonah Hill’s father even managed the band before they hit it big. They have spoken fondly about their carpool days and mutual love for music as high schoolers.
Gwyneth Paltrow and Kerry Washington
The Oscar-winning actress and the Scandal star were both students at the all-girls preparatory school Spence School on the Upper East Side of Manhattan. In a fun twist, Paltrow was the president of the a cappella group Triple Trio, which Washington aspired to join and eventually became co-president of herself. This surprising connection showcases the close-knit world of New York’s elite schools.
Ansel Elgort and Timothée Chalamet
Before they were both nominated for major awards in the same year, these two heartthrobs were competing for attention at Fiorello H. LaGuardia High School of Music & Art and Performing Arts in New York City. The two are graduates of the prestigious performing arts school and even played on the basketball team together. They represent a new generation of talent emerging from the same famous alma mater.
Tupac Shakur and Jada Pinkett Smith
The legendary rapper and the prominent actress/talk show host shared a close bond as high school classmates at the Baltimore School for the Arts. Jada has described her relationship with Tupac as “the greatest love” and a deeply spiritual connection. Their friendship is a well-documented and bittersweet piece of music and film history.
Cameron Diaz and Snoop Dogg
Believe it or not, the actress and the rapper were classmates at Long Beach Polytechnic High School in California, though they were a year apart. It’s a truly unexpected pairing from the 1980s high school scene.
Zach Braff and Lauryn Hill
The Scrubs actor and the Fugees singer both grew up and attended Columbia High School in Maplewood, New Jersey. They were close friends in high school, with Braff even attending Hill’s Bat Mitzvah.
Jay-Z and Busta Rhymes
Before they were hip-hop titans, these two New York rappers were students at George Westinghouse Career and Technical Education High School in Brooklyn. The story goes that they even had a legendary rap battle in the school cafeteria. Jay-Z won the battle, but both went on to become icons of the music industry.
Neil Patrick Harris and Freddie Prinze Jr.
Both actors attended La Cueva High School in Albuquerque, New Mexico, in the late 1980s and early 1990s. While not in the same graduating class, they both started their careers around the same time and rose to teen idol fame. This makes for a surprising connection between a sitcom star and a teen movie lead.
Kate Hudson and Zooey Deschanel
The two actresses attended Crossroads School for Arts & Sciences in Santa Monica, California, which is known for its celebrity alumni. They were classmates and even performed in a high school production of Man of La Mancha together, where Deschanel played a horse and Hudson played the niece of Don Quixote.
Lady Gaga and Nicky Hilton
The pop superstar and the Hilton heiress both attended the Convent of the Sacred Heart, an exclusive all-girls Catholic school on the Upper East Side of Manhattan. Though they didn’t run in the same circles, they were certainly aware of each other. This high school connection provides a fascinating contrast between two different types of celebrity fame.
Lenny Kravitz and Nicolas Cage
The rock musician and the Oscar-winning actor were classmates at the prestigious Beverly Hills High School in the 1980s. They were classmates and even worked together on a high school production of “Oklahoma!”, where Kravitz played drums in the orchestra pit and Cage was on stage.
Rami Malek and Rachel Bilson
The Oscar-winning Bohemian Rhapsody actor and The O.C. star both attended Notre Dame High School in Sherman Oaks, California. They were classmates and were even in the same friend group, even starring as the leads in their senior year production of The Crucible.
Nicole Kidman and Naomi Watts
The Australian-born actresses became friends long before they graced Hollywood’s red carpets, having met while attending North Sydney Girls High School. Their enduring friendship is one of the most heartwarming in the entertainment world.
Camila Mendes and Cole Sprouse
The Riverdale stars have a history that predates their hit CW show, as they both attended New York University’s Tisch School of the Arts drama program. They weren’t close friends then and Cole has said he doesn’t remember her. Mendes has said she would see Sprouse around campus, and they had classes in the same building at one point, but they did not form a friendship at the time.
Ed Helms and Brian Baumgartner
Similar to their The Office co-stars John Krasinski and B.J. Novak, these two actors share a high school history. They were both members of the a capella group at The Westminster Schools in Atlanta, Georgia. Their shared background in music and performance led them both to careers in comedy and television.
Scarlett Johansson and Jack Antonoff
The actress and the Grammy-winning musician and producer attended the Professional Children’s School in New York City, a private school for aspiring young performers. Not only were they classmates, but they also dated briefly in high school and even attended prom together.
Jennifer Aniston and Chaz Bono
The Friends star and the activist/actor/musician were both students at Fiorello H. LaGuardia High School of Music & Art and Performing Arts in New York City. They were in the same friend group and would often hang out at Cher’s house after school.
Eddie Redmayne and Prince William
This unusual pairing saw the future Oscar winner and the future King of England as schoolmates at Eton College, the prestigious all-boys boarding school in Windsor, England. They were classmates, played on the same rugby team, and were both elected members of the elite Eton Society, an exclusive group of senior prefects.
John Krasinski and B.J. Novak
Known for their roles on The Office, these two were friends long before they played co-workers on a hit show. They attended Newton South High School in Newton, Massachusetts, together and were in the same class. In a fun coincidence, they ended up acting together on the show and B.J. Novak served as a writer and director.