1957 Pontiac Bonneville Convertible

America was slowly giving itself permission to have fun in the 1950s. The ’30s were economically devastating, and World War II and the recovery from the depression shaped the 1940s. The ’50s were different. Even though they became a period known for Ozzie and Harriet, Father-Knows-Best conformity, there was a groundswell of alternative popular culture growing. The faces of nonconformity were those of James Dean in Rebel Without a Cause and Marlon Brando in The Wild One. Elvis provided the soundtrack.

One only need look at the styling progression of ’50s Pontiacs to see the crescendo build. From the warmed-over postwar styling of the late ’40s, the volume was turned up a notch every year. However, although Pontiac had a V8 from 1955 on, its image as an upgraded Chevrolet was a tough one to shake.

Semon “Bunkie” Knudsen, who came on as Pontiac Division General Manager in 1955, knew which direction to take. Knudsen, who had said, “You can...