DAVID LETTERMAN – 1968 FERRARI 330 GTS – $2.7 MILLION

David is worth more than $400 million. Most of his earnings came from his gigs in Hollywood namely writing, producing, and hosting shows. He also did a little bit of investment in an automobile racing team. The exact estimate of how much the Hollywood host has in his bank account is a mystery as he has made numerous investments throughout the years outside of Hollywood, making his private life’s investments earn him more than he would have in the entertainment business.

As a car enthusiast, he owns many expensive cars and one of the best pieces in his collection would be the vintage 1968 Ferrari 330 GTS. It is also one of the most expensive cars on this list since this car costs around $2.7 million. The Hollywood host seems to have an expensive taste for rare exotic vehicles just like his late night counterpart, Jay Leno (who, himself, has an impressive garage).