Brad Pitt

Brad Pitt got to practice in attending one red carpet after another when he went to two proms as a teen. After his college stint in Missouri, he chased the bright lights of Los Angeles in pursuit of a career in the movies. He only booked small TV roles before his big break in the 1991 film Thelma & Louise finally came.

It was a no-stops trip to stardom from there as he was cast in films like A River Runs Through It and Interview With The Vampire. Now $300 million rich, Pitt has also ventured into producing with his latest project, Americanah, currently in the works.