I'll bite:
1970 Honda CB450, drove till I was 17 to avoid driver ed class.
1969 Dodge Charge R/T, paid 700, totaled twice, put 5k into it in 2 years sold for 250. Too much car for a 17 year old kid.
1969 Chevelle SS 396 4 speed, paid 350, needed another car as charger was always in the body...