3. 1955 Ford Thunderbird 
Source: Ford
In the early ’50s, Sinatra’s career had come dangerously close to collapsing, but by mid-decade, he had a second Oscar under his belt (for 1953’s
From Here to Eternity), and was the most famous entertainer in the world. With that came incredible wealth, and a healthy love of cars. Capitol Records bought Sinatra a black first-generation Thunderbird, which he was
photographed in regularly. He was also said to buy T-Birds for his closest friends – and favorite girlfriends.