34. Jay Leno – 1955 Mercedes 300SL Gullwing Coupe, Estimated $1.8 Million
There are plenty of celebs with a love of cars but Jay Leno takes the obsession to a whole new level with a collection of 286 vehicles – 169 cars and 117 motorbikes. He is the host of CNBC’s, Jay Leno Garage after all. Leno’s most costly vehicle is his 1955 Mercedes 300SL Gullwing Coupe.