By James Derek Sapienza
Frank Sinatra’s Car Collection: 10 of His Most Important Cars
1. Chrysler Convertible Source: Fiat Chrysler Automobiles

Before he was a star, Sinatra was one of countless “boy singers” in the New York area looking for his big break. According to James Kaplan’s biography The Voice, in the mid-’30s Sinatra got his first break with the group The Four Flashes not because of his talents, but because he owned a car, a green Chrysler convertible. With Sinatra in their ranks, the group could now get to shows a lot easier. Unfortunately for them, ‘Ol Blue Eyes quickly left them in the dust.