John Cusack | Chicago, Illinois

American superstar John Cusack, along with his sister Joan Cusack (who is just as famous) was born outside of Chicago. The 54-year-old actor was born in Evanston, Illinois. After a while, his family moved to Manhattan, New York. In fact, John was in the middle of completing his college degree at New York University before deciding it wasn’t for him. Acting was something he really felt passionate about. His career took off when he began taking roles for films in the early eighties.

Eventually, John became a huge success, and as of 2020, he’s been reported to have a net worth of $50 million. John was smart enough to invest his money in real estate properties. After all, it must have been part of his financial planning. He once owned a beachfront property in Malibu worth $2.1 million but was able to sell it for a whopping $10.3 million. Like a lot of famous celebrities, John is one of those who stays true to his roots. In fact, in 2005, he purchased a 5,000 square-foot condo worth $2.9 million located in his beloved Chicago.