1928 Mercedes-Benz S-Type 26/120/180 Sports Tourer – $5-6 Million

Mercedes-Benz is one of the first foreign companies to achieve significant success during the United States in the earlier years of the automobile industry. Some of its most expensive vehicles that hit the market were their S and K models, which were mainly delivered through a New York distributor in the 1920s. A unit of the four-passenger sports tourer was sold to singing star Al Jolson in 1928. Eventually, he sold it to Brooks Steven, an American industrial designer, in 1947.

The sports tourer is powered by a 6.7-liter 6-cylinder engine with an output of 120 horsepower with a four-speed manual transmission. Most cars in those eras can reach a speed of up to over 180 km/h. There were originally 150 units of these cars produced. Yet, only a few survived, making it one of the rarest vehicles in the world—buying one of these is a good investment. Ferdinand Porsche, an Austrian-German engineer and the eventual founder of the car company Porsche, was the chief designer of the Mercedes-Benz cars at the time.