The first was a home conversion of a 1920s or 30s Ford flat bed, flat head, with the fuel tank in front of the dash board, with brakes that mostly didn't work. I was 14 and bought it for $15 to drive around the farm, as it wasn't and couldn't be licensed. Then in succession came:

1955 Chevy street dragster purchased from teenage shade tree mechanic, a mistake I never repeated;
1959 Chevy, not classy, but reliable;
1970 VW, even less class, but more reliable;
1956 GMC pickup;
1976 Dodge pickup;
1980 Datsun pickup;
1979 VW Vanagon;
1982 Puegeot;
1989 Dodge Grand Caravan - great soccer mom and camping rig;
1985 Subaru;
1988 Toyota Camry;
2000 Subaru Outback;
2014 Subaru Outback.

Schwin fat tire;
Raleigh 10 speed;
Diamondback mtn bike;
Rodriguez 27 spd road bike;
Guerciotti 18 spd road bike;
Rivendell Ramboulett 27 spd touring bike;
Eddy Merckz 20 spd road bike;
Bottechia classic 14 spd Italian.