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The worst car I ever owned was a gently used 1968 Toyota Corona I bought in the mid 70s. Styling-wise think Soviet era Lada, but because it was a Japanese car it always ran.
That is until I made the mistake of letting one of my brother-in-laws borrow it. At some point in the evening he was driving back home on the freeway when the engine light came on, and the temperature gauge max'd out. Of course, he was bound and determined to get home. It finally gave out about 15 or so miles later. He left it on the side of the road, angry that I let him borrow such a clunker!
My other (good) brother-in-law helped me rebuild it. It lasted another 3 months. Turns out knuckle-head managed to warp the crank shaft (and we hadn't thought to check that before our rebuild).
Now a-days I carefully vet anyone who wants to drive any vehicle I own, and usually decline.
1980 something Chrysler LeBaron Turbo. Bought it from my grandmother in law (took it and gave money, cuz she couldn't see at night and still drove by following the white lines on the side of the road) with 32k miles in 1997. Drove in such a way as to never engage the turbo cuz the car shook like crazy when under acceleration. Parked in the garage one night shortly after having bought it. 15 minutes later our garage was on fire. The fuel line had broken and dripped onto something hot and ignited. Burned the garage and part of the kitchen. The grandmother in law, when she found out we got more in insurance for the car than what we paid her, wanted the extra money. She was a piece of work too.
Dodge Intrepid, which was constantly stalling, had to have both the transmission and rack & pinyon steering replaced after the 36,000 mile warranty ran out and before it hit 40,000 miles.
Second worst: Mitsubishi Lancer GT Manual. The clutch went at 30K miles. I replaced it with another standard transmission car where the clutch was still going strong after 100,000 miles when it was totaled by hail.
Every Ford and Jeep I've ever owned, and I've had two of each. Never, ever again will I buy anything other than a Toyota. I drove my '99 Taco for 15 years and almost 400,000 miles, nothing ever broke on it, ever, until the AC compressor finally gave out at mile 393,000 and something. My 2015 now has nearly 80,000 on it and again, no problems whatsoever (knocking on wood as I type).
If you think 'goto' is evil, try writing an Assembly program without JMP.
My Ferrari FXXK. Every time I come out of the store, there are four or five super-models around it, and the cab is quite compact so I can never get more than two in the passenger seat at a time. How can so many people think that we wealthy folks' lives are always perfect.