[h=2]6. 1962 Dual Ghia L6.4[/h] Source: RM Sotheby’s

By the early ’60s, Sinatra was the first king of Las Vegas, and he and his Rat Pack ruled the entertainment industry. Meanwhile in Detroit, Dual Ghia was pioneering the method of hand-picking its owners (a practice later cribbed by Ferrari) and found a perfect match in the Rat Pack. With Chrysler running gear and a hand-built body made in Italy by Ghia, the $13,500 L6.4 was one of the most exclusive cars in the world, with just 26 produced – and most of them going to celebrities. Despite their price and exclusivity, there was something off about Sinatra’s car. He had celebrity customizer George Barris install a number of fail-safe components, including a backup fuel pump and brake circuits. Today, just 17 of the cars survive. This ’62 fetched an impressive $362,000 when RM Sotheby’s sold it at Monterey back in 2013.