I bought both my 1964 Dodge Polara hardtop and convertible in 1980. My 1967 Coronet wagon came along in 1984, followed by a 1967 Coronet R/T in 1987. I still own the '64 hardtop (43 years), and the R/T (36 years).
I bought my first performance car when I was still in high school in 1965. This was a TriPower 345 h.p. 389 in a 1959 Pontiac Catalina 2-door post sedan. This WideTrack car was rare almost anywhere, but especially so up here in Ontario, where our Pontacs were mostly Chev. In 1967, I bought a 1962 Dart 2-door post sedan that was formerly a police cruiser. I quickly replaced the tired 313, 3-speed manual with a 383, 4-speed. I sold this to a friend in 1969, and bought a new 383 Super Bee that I kept until 1972. By this time, I was married and needed a sensible family car; a 370 h.p. 455 in a Buick Wildcat! This remains one of the best cars I ever owned.
In 2008, I purchased a very low mileage 2005 Hemi Magnum R/T wagon, that I kept until 2016. This was a very nice hot rod, that I sometimes miss. Double knee replacements made it hard to get into and out of due to its lowness, so I sold it to buy a 2015 Durango.
My very first car was a 1939 Buick coupe that I bought shortly after getting my driver's licence. Along the way, I have also had a 1937 Oldsmobile 8 sedan and a 1938 Packard Super 8 formal sedan. So, I have almost always had something collectible or high performance pretty well since I started driving.