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1. 1963 Pontiac Lemans convertible (bought used in 1972). Motor Trend Car of the Year! Someone at GM had the bright idea of putting the transmission at the rear. Between either the clutch or the transmission needing repair, the car was on the road maybe half the time.
As a plus, the engine was a 4-cyl with a 4-bbl carb, basically a 389 V-8 sawed in half.
2. 1980 Buick Skylark. First year of GM's infamous X-Cars. The interior plastic trim was made of the same plastic as a Coleman cooler. After a few years in the sun, it crystallized and you could scrape off chunks with your fingernail.
I gave it to my ex in a divorce and I learned that she didn't put oil in it when the warning light same on, and the engine seized up.