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14 Famous People Who Go Way, Way Back

It was the best of times and it was the awkwardest of times. Pre-coolness, these famous peeps were chillin'.

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1. Cameron Diaz and Snoop Lion

In an interview with Today, Diaz recalls the artist formerly known as Snoop Dogg being "very tall and skinny" and "wearing a lot of pony tails" back at Long Beach Polytechnic High School. What does Snoop remember about his relationship with the actress? "I might have sold her some of that white girl weed... you know... sticks and stems."

3. Jay-Z and Busta Rhymes

Busta once reminisced to MTV about rap-battling Hov in the cafeteria of Brooklyn's George Westinghouse High School: "He was so ill and his arsenal was so long... That was probably the first time I lost a battle that mattered." Who else attended GWHS? Christopher Wallace Jr., better known as THE Notorious B.I.G.


4. Charlie Sheen and Rob Lowe

Sheen and Lowe were good buddies at Santa Monica High School; also in their crew were pals Robert Downey Jr. and Sean Penn. Lowe recalled to Access Hollywood that Sheen used to "wear bulletproof vests to school because he thought the gangs were going to get him." Surprisingly cautious for a man who claims to have tigerblood.

5. Jeremy Piven and John Cusack

Piven and Cusack were close from an early age; they grew up together in Evanston, Ill., both attended a theater workshop run by Piven's parents, and even (years later) shared a Chicago-area apartment together. These days, however? The two reportedly do NOT get along; Piven has alluded that Cusack may be jealous of his successful career while Cusack denies these claims. OOOOOOO, drama.

7. Barbara Streisand and Neil Diamond

Speaking of chorale groups, this talented pair sung together in Brooklyn's Erasmus High School choir. Years later, they repped EHS by collaborating on their No. 1 hit "You Don't Bring Me Flowers (Anymore)."


8. Kevin Spacey and Val Kilmer

At Chatsworth High School in California, both of these rising stars were born. However, one of them apparently had a long way to go. In an interview with Esquire, Kilmer was quoted as saying that Spacey is "proof you can learn how to act. Because he was horrible when he first started." Twenty bucks if you can find someone who would describe Spacey's acting as "horrible" nowadays.

10. Jon Stewart and Anthony Weiner

The class of '84 and William & Mary hosted both the Daily Show host and his Weiner-tweetin' friend Anthony. After college, Stewart shared an apartment with Weiner's girlfriend at the time; Weiner spent most of his time there as he told City Scoops he was "bumming off of [his] girlfriend" while he lived at home with his mother. Nevertheless, Stewart had no choice but to rip on his ol' pal during Weiner-gate.

11. Jon Hamm and Sarah Clarke

Before he was Don Draper or she was Bella's mom in Twilight, these two actually went to prom together. Hamm surprised her 24 costar Kiefer Sutherland by dropping this knowledge on him during an interview. THERE'S NOTHING CASUAL ABOUT PROM NIGHT, JON.

12. Justin Long and Jonah Hill

Universal / Via

Before attending a made-up college together in Accepted, these funnymen were roommates at the New School. However, they went their separate ways due to excessive bickering. "We started getting into little fights," Long told Us Weekly. "He left the bathroom door open, didn't clean up. Little things like that."

13. Adele and Jessie J

At The BRIT School of Performing Arts in London, the singers used to eat lunch together and even have the occasional jam sessions, according to a snippet from Jessie J's autobiography. Crazy to consider how much footage of the two belting tunes over tuna sandwiches would go for nowadays.

14. Robin Williams and Christopher Reeve

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This epic friendship began when the two were roommates at Julliard. Allegedly, before becoming famous, the two promised each other that whoever made it would take care of the less fortunate one. Years later, after Reeve's accident, Williams offered to cover any medical costs that the family couldn't.