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Maintaining a childhood friendship can be tough at the best of times, let alone when you’re two A-list celebrities with millions of other people wanting your attention. But there are still a number of famous faces who have managed to achieve such a feat. Here’s a look at 20 famous BFFs who have known each other since they were kids.

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20. Maya Rudolph and Gwyneth Paltrow

This particular friendship was actually spawned from another. You see, songwriter Dick Rudolph and film director Bruce Paltrow became best buds at Tulane University. Then, decades later, their respective daughters Maya and Gwyneth became classmates. Perhaps encouraged by their parents, the two developed a bond that remained just as strong when they became stars.

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Indeed, while guest hosting Saturday Night Live in the early 2000s, Gwyneth paid tribute to Rudolph who had just landed a spot on the show herself. She told the audience, “This week has been real extra-special to me because one of my best friends is on the show now, and I’m so proud of her. She’s super-funny and talented, and I’m so glad she’s in the cast.”

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19. John Krasinski and B.J. Novak

John Krasinski can perhaps thank B.J. Novak for setting him on the path to Hollywood fame and fortune. For long before the pair starred in the American remake of The Office together, they attended the same high school. And it was there that Novak persuaded Krasinski to appear in a stage production he was planning.

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Now, Krasinski, who also played little league with Novak, had only previously acted once beforehand. And he’d played Daddy Warbucks in a staging of Annie during his middle school years. But after being approached by Novak, he decided to tread the boards once more and apparently caught the acting bug.

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18. Justin Timberlake and Ryan Gosling

Justin Timberlake and Ryan Gosling were buddies from a young age when they were cast on The Mickey Mouse Club in the early 1990s. And the pair soon became joined at the hip. Not only did they work alongside each other, they also enjoyed each other’s company in their spare time. And Gosling even briefly moved in with the Timberlakes when his mother returned to their Canadian homeland.

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In fact, in 2013 Timberlake discussed how much trouble he and Gosling got into during an appearance on The Jonathan Ross Show. He told the British host, “We were crazy. We, like, skipped tutoring. Going to the park, to the Honey I Shrunk the Kids set. We’d have milkshakes. Oh man, we were so gangster.”

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17. Tobey Maguire and Leonardo DiCaprio

One of the most high-profile BFFs, Tobey Maguire and Leonardo DiCaprio were often pictured partying together as they rose to fame in the 1990s. Now, the pair first met on the auditioning circuit as kids in the late 1980s. And despite the fact that Maguire nearly always lost out to DiCaprio for roles, they soon became close friends.

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Of course, Maguire would eventually land several leading parts himself, most notably Spiderman. And he even shared the screen with DiCaprio on The Great Gatsby. DiCaprio once told the Associated Press, “Every single choice I’ve made, I’ve talked to Tobey about and vice versa. We’ve had endless conversations about certain projects and argued with one another and supported one another along the way.”

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16. Adam Levine and Jonah Hill

Singer Adam Levine and actor Jonah Hill might not seem like the most obvious celebrity friendship. But the pair have known each other since they were tots. For their fathers had also been best buds since meeting in junior high at the principal’s office. “We basically lived together – we were in a carpool, sleepovers at each other’s houses, everything.,” Hill revealed during an appearance on The Howard Stern Show.

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What’s more, Hill insists that despite the monster success of Maroon 5, Levine hasn’t been affected by fame. He told Stern, “That is a guy who is exactly who he ever was, in a great way.” And in further proof of their friendship, the two-time Oscar nominee even officiated Levine and model Behati Prinsloo’s wedding in the summer of 2014.

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15. Neil Diamond and Barbra Streisand

Who knew that two of the 1970s most popular artists had first began making sweet music together as school kids? Yes, before conquering the US Hot 100, Barbra Streisand and Neil Diamond regularly used to sing with each other in the choir at Brooklyn’s Erasmus Hall High School. However, the latter had little idea that the pair would go on to be megastars at the time.

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Yes, Diamond reportedly said in an interview in 2018, “We were two poor kids in Brooklyn. We hung out in the front [of the school] and smoked cigarettes.” The two musical icons did eventually head into the studio in 1978 to record classic breakup anthem “You Don’t Bring Me Flowers.”

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14. Clare Danes and Morena Baccarin

Jessica Brody and Carrie Matheson aren’t exactly the best of friends on Showtime’s popular CIA drama Homeland. In fact, the two have never met each other face to face, even though one had an affair with the other’s husband. But off screen, the actresses playing them, Morena Baccarin and Clare Danes, have known each other since middle school.

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In a 2012 interview with TV Guide, Baccarin recalled, “When I was seven, we moved to New York because my dad’s job was transferred. I grew up in the West Village and went to the New York City Lab School for junior high. Clare was there at the same time! We were somewhat friendly, so when Homeland came up, it was great.”

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13. Timothée Chalamet and Ansel Elgort

Timothée Chalamet and Ansel Elgort are two of the hottest Hollywood stars of the Instagram generation. And they’ve been able to revel in their success together since their days at New York’s LaGuardia High School of Music and Art and Performing Arts. Apparently, the two developed a close friendship due to their passion for both acting and the basketball court.

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In 2017 Elgort captioned an image of himself and Chalamet sitting together at a New York Knicks basketball game. And he wrote, “LaGuardia High School pride. It’s really crazy, Timmy and I played on the same basketball team, we had the same drama teacher Mr. Shifman, we had the same science teacher Mr. Singh, and then in the same year, both of us are nominated for a f***ing Golden Globe!!!”

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12. Nicole Kidman and Naomi Watts

Nicole Kidman and Naomi Watts are undoubtedly two of the most successful actresses ever to emerge from Australia. The pair have six Academy Award nominations between them, with the former winning best actress for 2003’s The Hours. And they appear to have supported each other every step of the way.

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You see, Watts and Kidman first met as teens at North Sydney Girls’ High School and later appeared together in 1991 drama Flirting. The former told People in 2012, “We’ve gone through a lot together over a significant amount of time. That history binds you. We have a strong respect and love for one another.”

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11. Prince William and Eddie Redmayne

Eddie Redmayne can perhaps lay claim to having the most impressive celebrity childhood friend. Yes, because the Oscar winner used to hang out with none other than the future King of England, aka Prince William. The pair attended Eton College together in Berkshire, United Kingdom. And while appearing on Watch What Happens Live, Redmayne admitted there was one significant benefit of having such a high profile bud.

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Recalling their time on the rugby field together, Redmayne told host Andy Cohen, “I always felt a bit sorry for him because basically any school you’d play [against], all they wanted to do was tackle Prince William in order for them to say, ‘I tackled Prince William.’ So, if you were standing next to Prince William, it was actually quite easy [to do so] and quite fun!”

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10. Jennifer Aniston and Chaz Bono

This is perhaps one of the most unexpected friendships on the list. Back in the 1980s both Jennifer Aniston and Chaz Bono attended the same high school in New York City. And when an old photo of the actress and Sonny and Cher’s daughter surfaced in 2011, the internet almost broke.

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Furthermore, Aniston spoke about her teen friendship with Bono, who has since transitioned to a man, to Allure. The Friends star said, “Every day a group of us would go to Chaz’s house after school.” Sadly, Aniston also revealed that she and Chaz haven’t spoken to each other in a while.

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9. Matt Damon and Ben Affleck

Matt Damon and Ben Affleck became bona fide A-listers at the same time thanks to their performances and Oscar-winning script for Good Will Hunting. And the pair had dreamed of such a moment since becoming friends in the early 1980s. In fact, Affleck once told Parade that their shared passion for acting made them inseparable.

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Affleck said, “Before Matt, I was by myself. Acting was a solo activity where I’d just go off and do something, act in a little TV show or something, and no one understood it. All of a sudden I had this friend Matt, and he gets it and wants to do it and thinks it’s interesting and wants to talk about it.”

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8. Lee Pace and Matt Bomer

In 2011 Lee Pace appeared on the Broadway stage for the first time in A Normal Heart, while three years later Matt Bomer graced the HBO adaptation. But this wasn’t the first time that the two actors’ careers had aligned. The pair had actually co-starred in several productions together while attending Texas’ Klein High School.

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Pace and Bomer have remained friends ever since, and in 2014 Pace recalled their high school years in an interview with Buzzfeed. “He was a year older than me,” he said. “We did The Diary of Anne Frank. He was Mr. van Daans and I was Mr. Dussel.”

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7. Macaulay Culkin and Elijah Wood

Macaulay Culkin became the biggest child star in the world thanks to his leading performance in Home Alone. Little surprise then that he bonded with one of the few other kids who had any idea about being launched to fame at such a young age. Indeed, while filming 1993’s The Good Son, Culkin became buds with co-star Elijah Wood.

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Furthermore, the two youngsters were tutored alongside each other while shooting the thriller. And they’ve apparently continued to have each other’s backs while dealing with life after child stardom. Answering a fan’s question on Twitter in 2018, Culkin joked, “Of course we’re friends. @elijahwood and I will always be brothers… until he inevitably drops me off a cliff.”

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6. Kim Kardashian and Paris Hilton

It seems unthinkable now. But there was a time when Kim Kardashian was better known as Paris Hilton’s BFF rather than a celebrity in her own right. And Kanye West’s other half had grown up with the star of The Simple Life as their incredibly rich parents were also friends.

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And in a 2019 episode of reality show Keeping Up with the Kardashians, Kim freely admitted that she owes a lot to the Hilton Hotel heiress. She told sister Khloe, “I really would wanna do anything for her. She literally gave me a career, and I totally acknowledge that.”

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5. Big Boi and Andre 3000

With six Grammy Awards and sales of more than 25 million worldwide to their name, Outkast are one of the biggest acts in hip-hop history. And the pair’s route to success all began at a shopping center when the duo were both just 16. Yes, Andre 3000 and Big Boi, aka André Benjamin and Antwan Patton, first met each other in 1992 at an Atlanta mall.

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What’s more, the pair attended the same Tri-Cities High School where they regularly showcased their skills in various rap battles. Under the guidance of local production team and future TLC hitmakers Organized Noize, the duo later formed Outkast. And the rest, as they say, is hip-hop history.

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4. Lauryn Hill and Zach Braff

Here’s one childhood friendship you definitely didn’t see coming. Yes, back in the 1990s Grammy-winning R&B icon Lauryn Hill used to mix in the same circles as nerdish Scrubs lead Zach Braff. Yes, the pair both attended Maplewood’s Columbia High School and Hill even showed up at Braff’s bar mitzvah.

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Chatting with Jane magazine in 2006, Braff recalled, “There was a game called Coke and Pepsi. You’d have a partner, and one person was Coke and the other Pepsi. Depending on what the DJ would yell, you had to run and get on that person’s lap. And Lauryn was my Coke and Pepsi partner.”

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3. Amanda Seyfried and Mae Whitman

Born in Los Angeles in 1988, The Duff star Mae Whitman is a good three years younger than fellow Hollywood actress Amanda Seyfried. But that didn’t stop her from forging a close friendship with the Mamma Mia lead in their early days. And the pair’s bond has remained just as strong as they have both risen to fame.

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Indeed, Seyfried and Whitman were regularly pictured together on the red carpet during the early 2000s. They showed up at the 2005 MTV Movie Awards with their arms around each other. And they also sported matching denim outfits at the launch of the second annual Teen People Young Hollywood Issue.

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2. Laura Linney and Brooke Shields

Brooke Shields appeared to have several friendships with future stars during her early years. In the early 1980s she forged a bond with Matt Dillon as the pair both attempted to crack Hollywood. And in her even younger days she became friends with another actress, The Big C star Laura Linney.

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Yes, Shields made the internet go “aww” in 2020 when she posted an adorable throwback of the pair sitting on a swing together. The Blue Lagoon star captioned the Instagram image, “went way back into the archives for this one #tbt with @itsmelauralinney.” Actress Mariska Hargitay remarked, “That may be the sweetest pic I’ve ever seen.”

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1. Courtney Love and Drew Barrymore

A rebellious singer approaching her twenties perhaps isn’t the ideal person for an eight-year-old child star to make friends with. But Drew Barrymore wasn’t your average eight-year-old. The E.T. star struck up an unlikely bond with future Hole frontwoman Courtney Love after meeting in a bathroom. And it was Barrymore who reportedly had a cigarette in her hand.

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Barrymore discussed how awestruck she was of Love while appearing on Watch What Happens Live. She said, “We were going in to see like a back play at a coffee house, and the bouncer said, ‘I’m sorry, you can’t come in. You don’t have a backstage pass.’ And Courtney looked at him and goes, ‘My face is a backstage pass.’ And then swept him aside and just walked in and I was still left there standing. I mean, kinda awesome.”