20. Jake Gyllenhaal

Net Worth: $65 million*
Wealth Inherited From: Stephen Gyllenhaal

Jake Gyllenhaal is the offspring of Stephen Gyllenhaal, a renowned Hollywood director. He is the sibling of actress Maggie Gyllenhaal. His mother, Naomi Foner, is a screenwriter. He was born in Los Angeles and he attended Columbia University. He began acting as a child, appearing in the 1991 movie.

He had his first breakthrough role in the film “October Sky”, where he played Homer Hickam. He won an Indie Award for his role as Donnie Darko in the eponymous movie. He acted alongside his sister Maggie in the film, which received critical acclaim. He has also appeared in Focus Features movies.