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First (post war) vinyl top at Cadillac was on the Eldorado Seville when that body style started in '56. But they were never the padded variants the '70s had; right tight against the steel. Eldorado Seville '56-60, then the 'E' went to all convertibles until the '67 clean sheet car (which had the option again).

Not seeing a non-'E.S.' vinyl top until the '64 Series 60 Special.

At Pontiac- the first vinyl roof was '62. I remember looking at a derelict '62 Grand Prix at a gas station decades ago, and the white vinyl roof had peeled over & was draped off one side, like a bad toupe' in a stiff wind.
 
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