Jay Leno | 1955 Mercedes-Benz 300SL Gullwing Coupe | Approximately $1 million

Jay Leno is one television personality who certainly doesn’t need any introduction. Leno first rose into prominence as a stand-up comedian for many years. After his successful career in stand-up comedy, Leno quickly became the host of The Tonight Show on NBC from 1992 until 2009. Today, Leno still appears in several television productions, including his hit show Jay Leno’s Garage, showing off some of the most prized cars in the automotive industry.

Besides his successful television career, Leno takes pride as one of the biggest car enthusiasts in the world. Leno currently has a collection of over 280 vehicles. It’s safe to say that Jay pays a hefty amount for the insurance bill for all of his cars. Interestingly, one of the cars in Leno’s garage is a 1955 Mercedes-Benz 300SL Gullwing coupe with a value of over $1 million.