Retro | Entertainment

11 Childhood Friendships That Made It To Hollywood

To make it to Hollywood is an incredible feat. It's rare that you or one of your friends becomes a major celebrity. But can you imagine if you and your best friend became a Hollywood star? How crazy would that be?

Take a look at some of the celebrities you never knew were childhood friends.

Tobey Maguire and Leonardo DiCaprio

These two mega-stars used to go to auditions together when they were kids. DiCaprio recalls wanting to be friends with Maguire so badly, he yelled at him from across a Hollywood lot asking for his phone number.

Elijah Wood and Macauley Culkin

The Lord of the Rings star and Home Alone cutie appeared in the 1993 thrilled The Good Son and even keep in touch to this day. Despite everything Culkin has gone through, it's nice to know he still has true friends.

Chaz Bono and Jennifer Aniston

Before she was Rachel on Friends, Aniston was a student at LaGuardia High School in New York. Cher's son (then daughter) Chaz Bono (then Chastity Bono) also attended the school, and together they would often hang out at the Cher household!

Justin Timberlake and Ryan Gosling

This friendship actually started in Hollywood, but stood the test of time. When Gosling got his part on The Mickey Mouse Club, his mom was still working up in Canada. Timberlake's mom stepped in and became Gosling's legal guardian for six months until his mom could join him in Florida.

Kim Kardashian and Nicole Richie

The two Hollywood starlets have been friends since they were 13, hanging out with the same people during school.

Courtney Love and Drew Barrymore

Barrymore was a star from a young age, and at 19 she fell into the party scene which involved Courtney Love. The two became very fast friends, and even after Barrymore sobered up, she and Love stayed close. The actress is even godmother to Courtney Love and Kurt Cobain's daughter, Frances Bean.

Matt Bomer and Lee Pace

You know Bomer from the show White Collar and the movie Magic Mike. As for Pace, he was in the Lord of the Rings franchise and the show Pushing Daisies. They met in the drama club at high school and bonded over their desire to get out of the small town they were living in.

Wes Anderson and Owen Wilson

Wilson and Anderson met in college, and became fast friends. They met in a playwriting class, then became roommates and best friends. Owen Wilson has appeared in almost every single one of Wes Anderson's films.

Brad Pitt and Christina Applegate

Pitt and Applegate were extremely close, even before he became famous! Applegate was just starting out on Married with Children and the two began dating in 1989. Applegate dumped Pitt, though, when she left the MTV Movie Awards with another guy.

Brooke Shields and Matt Dillon

Shields and Dillon were practically inseparable at a young age, to the point where it was always speculated that they were dating. Dillon almost starred with Shields in Blue Lagoon, but he wasn't quite comfortable with the amount of nudity it required.

Sean Penn and Nicolas Cage

Before they were famous, Penn and Cage were struggling to break into the industry. They both got their big break in the movie Racing With The Moon in 1984.