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Myself, 1931 model T truck, drove a 1951 Buick to school (straight 8 and Dynaflow trans), and a 1939 Pontiac (250 chevy six and turbo 350 trans) for a few months, too.
Drove a 1965 Ford tow truck a lot, too. Not to mention '65 & '66 Mustang converts with Shelby running gear, '66 GT350H, '69 BOSS 429, '64 GTO convertible, '58 Chev, '62 Caddy, MINT '41 Olds, '51 Lincoln, 69 Elco, but the first car I drove (at age 9) was a '62 Falcon Ranchero with 3 on the tree.
Grew up in a wrecking yard in the '70's. Great time to be a kid!
 

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Up until 2000, the newest car I had owned was a 69 Camaro and I was daily driving a 53 Willy's aeroace. Learned to drive with a 41 ford, oldest was a model A. All the cars were stock
 

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I've steered some pretty old cars while moving them around from place to place by pulling them with another vehicle. But actually drove? Hmmm. Going to have to give that some thought.
 

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The oldest car I have owned and driven is my 33 Chevy that I own now, (had a 34 Ford PU before that),..but I've driven a few older T buckets,...1919,..1923,... and countless 30s, 40s, 50s and 60s cars and trucks that I've either flipped or were owned by friends.
 

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A 1903 Sears. Owned/restored by a neighbor.
 

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I used to alternate daily driving duties between a 55 T-Bird and my 67 SWB in the early 2000s. I drove the 67 to TX in 2015 from CA, and still drive it a few times/week.
 

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57 baja bug
63 Chevy short box
Neither of them in stock form.
 
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