In 1949, Jimmy’s father bought him a used ’39 Chevy.

In May 1954 Jimmy purchased a red MG and later purchased a white ’55 Ford stationwagon with wood paneling.

In March 1955 he bought his Porsche 356 1,500cc Super Speedster convertible; and in September 1955 Jimmy bought his silver Porsche 550 Spyder, he had the number 130 painted on the hood, and on the back end of the car, he commissioned car customizer George Barris to paint his nickname "Little Bastard," the nickname he got from Bill Hickman, who had been his dialogue coach on "Giant."

James Dean's uncle Marcus bought him his first motorcycle, a 1947 Czech Whizzer. Jimmy also owned an English cycle, a Harley, a 500cc Norton, an Indian 500, an Italian Lancia scooter and a British Triumph T-110, which had "Dean's Dilemma" painted on the side.