In 1972 LIFE magazine went on a road trip with Flip Wilson. Wilson, one of the top TV performers of his day, drove a Rolls Royce with the personalized license plate KILLER, after the never-seen boyfriend of the Geraldine character on his show. On the road trip, a care-free jaunt through the beautiful Southwest, writer P.F. Kluge observed “Flip’s enjoyment of driving is almost palpable. He leans back against the headrest, props a foot on the dashboard, holds his hand in the air, waving at nothing but the breeze.”

Today the piece of personal technology  that people are more likely to be infatuated with is their phones. But for much of the 20th century, the car occupied an exalted place in the American imagination. With the beginning of mass production in 1927 and the spread of suburban living after World War II, cars became the new place that we spent our time, and the expression of both status and style.

Now people care about fuel efficiency more than fins. The push now is toward cars in which people hand the driving over to a computer. But Flip and the people in these photos took joy in being behind the wheel.

This three-wheeler was an experimental model that appeared in a 1945 LIFE story touting the automotive lifestyle in California.

Photo by Nina Leen/]/The LIFE Picture Collection © Meredith Corporation

The car-hop was another sign of the automotive lifestyle in 1945 California.

Photo by Nina Leen/]/The LIFE Picture Collection © Meredith Corporation

The LIFE story on the new automotive lifestyle referred to Herbert’s as a “drive-in restaurant.”

Photo by Nina Leen/The LIFE Picture Collection © Meredith Corporation

This Messerschmidt from 1953 provides a snug ride.

Ralph Crane/The LIFE Picture Collection © Meredith Corporation

The clothes? Jacques Fath. The tower? Eiffel. The car? A 1947 Delahaye.

TONY LINCK/The LIFE Picture Collection © Meredith Corporation

This photo of a man and his Cadillac was from a 1951 story on ranchers who were raking in the bucks.

Loomis Dean/The LIFE Picture Collection © Meredith Corporation

Ice cream cones (melting on the outside but not on the inside) demonstrated advances in air conditioning in 1952.

John Dominis/The LIFE Picture Collection © Meredith Corporation

Here’s another kind of cool: Steve McQueen and his Jaguar, 1963.

John Dominis/The LIFE Picture Collection © Meredith Corporation

Cool cars

A boy admired the Cadillac display at auto show in New York, 1956.

Photo by Walter Sanders/The LIFE Picture Collection © Meredith Corporation

This Lincoln Futura, a concept car, appeared in the Debbie Reynolds movie It Started With a Kiss. A few years later another version of the Futura, with a darker paint job, became the Batmobile in the Batman television show.

Loomis Dean/The LIFE Picture Collection © Meredith Corporation

Press photographers covered the John Kennedy campaign on the back of a Cadillac, 1960.

Paul Schutzer/The LIFE Picture Collection © Meredith Corporation

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