4. 1956 Continental Mark II
Source: Ford
Spun off into its own brand in 1955, the Continental Mark II was one of the most beautiful luxury cars of the era. It was also one of the most expensive; at $10,000, it was twice as expensive as a Cadillac, and cost more than the Rolls Royce Silver Cloud – and
Ford still lost money on each one sold. Its combination of exclusivity and style made it a natural fit for Sinatra, and he could be seen driving his Continental II around Las Vegas and Palm Springs, California.