Frank Sinatra's Car Collection Represented His Style Well

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These cars are almost as fascinating as 'Ol Blue Eyes himself.

The Chairman of the Board, Frank Sinatra, is one of the most famous performers of all time. Generationally, nobody eclipses him, and it would be a heated argument to argue that any other name exactly as recognizable, maybe Elvis could stand up to the test. Regardless, Frank Sinatra was a very interesting man, with a famous love of the finer things in life. So what kind of cars did Frank Sinatra prefer? Let's dig in.

Chrysler Convertibles

Before getting his big break, Sinatra rolled around in a green Chrysler convertible. The story about this car goes that it was the reason he got his break with the group The Four Flashes. It's unclear which year the Chrysler was, but it was in the 1930s when that happened, so it's safe to assume it was like a mid-30s model. There was another story about Frank taking Nancy on their honeymoon in a brand new 1939 Chrysler convertible, and Frank was pictured driving around in a 1942 Chrysler Convertible.

1955 Ford Thunderbird

The 1950s were an interesting time for Frank, with him coming out on top in 1953 with a second Oscar win, pushing him into the spotlight as the most famous entertainer in the world. His 1955 Ford Thunderbird was giving to him by Capitol Records, since it was definitely in their best interest to keep him happy.

1956 Continental Mark II