Only two SSJs were ever built in Duesenberg. This rarity made it the costliest American car ever when it was sold in July 2018 at Pebble Beach for $22 million. This particular SSJ was once owned by Gary Cooper, a Hollywood star.

The SSJ was one of the most powerful cars of its era with a 400-bhp inline eight-cylinder motor. ¹⁾

The 290 MM was developed by Ferrari for the Mille Miglia (the source of its MM moniker), for the 1956 World Sportscar Champion. Scuderia Ferrari ran that 290 MM in 1956-57 and led him to the victory of a private team including Juan Manuel Fangio, Phil Hill and Sir Stirling Moss. It has been sold for $22,005,000. ²⁾

The Aston Martin DBR1/1 from 1956 is one of the latest additions to this list; it became the most expensive British car ever sold at Monterey Car week in 2017 when it sold for $22.5 million. In 1959, in the hands of Sir Starling Moss, it was the first of five DBR1s and enjoyed a considerable race success. ³⁾

Sold for $26,400,000, it is one of only three Ferrari GTB/C Special models which were designed to accompany its new 275 GTB race car by Maranello in late 1964 and the beginning of 1965. The 275 GTB/C Specific was significantly lighter and quicker than a standard 275 GTB road car with aluminum bodywork, a lighter chassis and a tuned V12 engine, with a 70bhp extra mounted lower on the vehicle to bring the center of gravity closer to the track. This 275 GTB/C Speciale never witnessed competition, but one of the other cars finished third overall in 1965 at Le Mans. ⁴⁾

The Ferrari 275 GTB/4 NART Spider, fully restored, was one of just 10 in the world in 2013 when it sold for $27,500,000. It had a long history, including an appearance in the film The Thomas Crown Affair with Steve McQueen.⁵⁾

Ferrari 290 MM, the most expensive car sold ($28,050,000) in New York City in 2015, and RM Sotheby's most costly car ever sold at that time, was sold in the New York City category. It was constructed in 1956 in the Mille Miglia competition for Juan Manuel Fangio, and subsequently took on a distinguished career. The car is one of four in existence and has been driven by names such as Wolfgang von Trips and Alfonso de Portago, who have been driving the car throughout its life. ⁶⁾

Driven by the five-time world champion of Formula One, Juan Manuel Fangio, the Grand Prix W196 by Mercedes-Benz achieved a sale price of $29,600,000 at the 2013 Goodwood Festival of Speed. The car was sold as if it had just rolled off the track with visible defects and a slim layer of grime. You pay all the money and they don't even run a car wash for you! ⁷⁾

The car has done everything since the first race at Sebring 12 Hours, via the Mille Miglia and finally Le Mans. It was sold for $35,700,000 in 2016 in Paris. ⁸⁾

In 1962, the Ferrari 250 GTO Berlinetta was turned into a record four years for the most expensive car ever sold at an auction in 2014. The FIA World GT champion was built to compete in 1963 and won. Ferrari only constructed 39 250 GTOs. This 3851GT was sold for $38,115,000. ⁹⁾

Two decades before its sale, Ferrari enthusiast and vintage racer Gregory Whitten owned this particular 250 GTO: Chassis No. 3413 GT. None other than Le Mans winner Derek Bell drove it to the auction block, and the auctioneer opened the bid at $35 million. Over the course of 10 minutes, three bids were placed for the car, reaching a final bid of $48,405,000, which exceeded the previous record by over $10 million. ¹⁰⁾