As if it isn’t cool enough to grow up and become rich, wealthy and super famous, imagine getting to do it along side an old pal! Fun!
1. Elijah Wood & Macaulay Culkin
It has been over two decades since Elijah Wood and Macaulay Culkin began their friendship. Even to this day, they still have a tight bond and think highly of each other.
2. Cameron Diaz & Snoop Dogg
This pairing seems really bizarre, but what happens in high school is never forgotten. Actress Cameron Diaz and rapperSnoop Dogg have at least one thing in common: they attended the same high school and rubbed elbows throughout their educational experience. Cameron even said that she remembers snagging some weed from Snoop! At the Long Beach Polytechnic High School, Cameron and Snoop were classmates with other famous faces, such as Warren G and Nate Dogg.
3. Ben Affleck & Matt Damon
These two have been friends for years! Growing up in the same area of Boston, these two connected and caused an explosion of awesomeness on the Hollywood movie scene!
4. Kim Kardashian & Nicole Richie
If you think about it, it just makes sense that Kim Kardashian and Nicole Richie knew each other from a young age. The two female celebrities have known each other since their ages were in the single digits, and they attended the schools growing up. In the early 1990s, Nicole had a 12th birthday party at Michael Jackson’s Neverland Ranch, and 13-year-old Kim Kardashian attended, as did Gaby Hoffmann and a handful of other girls.
5. Alyssa Milano & Corey Haim
When actor Corey Haim passed away from a drug overdose in 2010, there were so many celebs who shared their condolences and wishes for peaceful rest. One of them was Alyssa Milano, who had a long-term connection to Corey. The two had dating between 1987 and 1990, and they had known each other during their youth. The pictures are proof: Alyssa and Corey look embarrassingly smashing in their late 1980s clothing.
6. Justin Timberlake & Ryan Gosling
Want to embarrass two dudes Hollywood? Then show them a throwback photo of them starring on The Mickey Mouse Club. Timberlake and Gosling were both cast mates on the famed Disney show, and it helped to propel both of their careers.
7. Adam Levine & Jonah Hill
It may not seem like a solid pairing, but musical master Adam Levine and teddy bear actor Jonah Hill have been friends since they were young punks. Apparently, both Adam and Jonah found themselves at the principal’s office back in middle school. That’s not too hard to believe, is it? Ever since that fateful day, Adam and Jonah have been best buds
8. Owen Wilson & Wes Anderson
If you put two and two together, you will see that there is a very special relationship between Owen Wilson and Wes Anderson. While Owen went on to pursue an acting career, Wes became one of the most well-known film directors in Hollywood. And Owen has appeared in almost all of Wes’ films. That’s because the two of them are best friends, and it has been that way since they were young. And get this: they even lived together as 2nd-year roommates at the University of Texas in Austin.
9. Taylor Lautner & Victoria Justice
Just two young and adorable actors who are trying to become Hollywood famous. It was the childhood reality for Taylor Lautner and Victoria Justice. The two young stars have been friends since before they were even known. As tiny adolescents, Taylor and Victoria would hang out and support each other in their acting endeavours.
10. Nicolas Cage & Sean Penn
The two dudes have known each other since they were adolescents, and yet nowadays there seems to be more bad blood between them than good. Sean Penn slammed Nicolas Cage’s ego and stated that he was not an actor anymore. Maybe this long lived bromance has come to an end.
11. Jennifer Aniston & Chaz Bono
Both Jennifer and Chaz attended the LaGuardia High School of Performing Arts, and a 1987 gem of a picture shows the two stars posing together at school. This was before Chaz underwent gender transition surgery to become male, and apparently, Chaz’s teenage home was the place to go after school to hang out.
12. Aubrey Plaza & John Gallagher, Jr.
Their friendship ended up progressing into romance, and Aubrey and John were actually an item for a period of time. As teenagers, they both belonged to the same theatre troupe and Aubrey was John’s very first girlfriend.
13. Gwyneth Paltrow & Maya Rudolph
Gwyneth Paltrow and Maya Rudolph continue to keep in touch with each other, and they have a long-running friendship that started back when they were just young girls. They even attended the same elementary school together and stayed by each others’ side throughout high school.
14. Selena Gomez & Demi Lovato
They are the girl power duo that has been satisfying fans for years. Selena Gomez and Demi Lovato were both Disney Channel sweethearts, but their friendship and their collaborative acting goes back way further. The two actresses were childhood stars on the show Barney & Friends, starring on the show together when they were both just 7 years old.
15. Leonardo DiCaprio & Tobey Maguire
For the past quarter of a century, famous Hollywood actors Leo DiCaprio and Tobey Maguire have been buddies. The two of them were together in all their glory in the film The Great Gatsby, and it was like old times – except they were rich and famous now. The two guys met in the late 1980s, when they were both young adolescents who were interested in acting.
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