Jay Leno – Mercedes 300SL Gullwing Coupe 1955 – $1.8 Million

Even during his earlier years, Jay Leno was already a natural when it came to comedy. After finishing his college studies with a bachelor’s degree in speech therapy, Jay proceeded to work as a stand-up comedian. Soon after, in 1992, he received the honor of hosting The Tonight Show, a role he kept until his final episode in 2014.

With an estimated net worth of $350 million, it would come as no surprise to know that Jay has spent a good portion of his wealth on his vehicles. In fact, he already has over a hundred rides kept safely in his garage. Among these many lovely beasts include classics like the 1966 Oldsmobile Toronado, a 1909 Stanley Steamer, a 1986 Lamborghini Countach, and a 1963 Chrysler Turbine. With that said, the former talk show host is also no stranger to more modern pieces like the Audi R8 Spyder, a 2014 McLaren P1, and a Tesla P90D.