Jay Leno | McLaren F1 | $12 million

For his start in the entertainment industry, Jay Leno performed a comedy routine on The Tonight Show. He eventually made his way to landing minor roles in films and TV shows. Not long after, though, Jay finally gained widespread fame and recognition for his work as the show host of The Tonight Show with Jay Leno.

While he may have the makings of a true comedian and entertainer, Jay is also known for his fondness for collecting cars. Thanks to his career in the entertainment industry, Jay has had the chance to spend an astounding amount of investment money on his collection. With that said, the most prized vehicle in his garage would undoubtedly be this McLaren F1. While its name alone already radiates an aura of class, this beauty is also quite a rare gem in the automobile community – only 107 units were manufactured.