Oh, so many:
My first, 1972 Buick Skylark Custom, 2dr hardtop. 350-2bbl, TH400 tranny (the original TH350 burned out) Ended up junking it because the frame rusted out.
1977 Olds Cutlass, 350 4bbl. Got to drive it 3 weeks after getting it goiing before it blew out both head gaskets.
1978 Monte Carlo, 305 2bbl. Drove it for a couple of years. Finally spun out about half the rod bearings.
1969 Dodge A100 van, 225 Slant 6 2bbl. Ran beautifully until someone spiked my gas tank.
1990 Crown Victoria, fuel-injected 5.0 litre. Was starting to wear out after driving it for several years, let the insurance take it after s stupid kid caved in one of the rear quarters.
1998 Cadillac Deville Concours, 4.3 litre Northstar. It was a Northstar. Heads cracked after it popped a water pump. Traded it in on my current Malibu.
Yeah, they were rusty and crusty, but I miss every one. I'd take back the Volare if I could attack it with a sledgehammer.