Probably going back too far for you guys but...
60 Chevy. Great car. Easiest car in the world to work on.
66 Rambler. Tranny died after 10 years.
89 Ford Escort. Started being a money pit after 50K
97 S-10. Beat the shit out of it but it's still going after 80K
97 Viper GTS. 30K track miles and never a wrench on it.
98 Viper RT/10 70K hard miles. New timing cover gasket at 30K.