Worst: toss-up between:
'77 Plymouth Fury, tranny went immediatly following the warranty, paint was flaking and fading and numerous gadgets inside were falling off;
'95 Grand Cherokee, rear-end went just before warranty did, wiring harness on drivers side went just after warranty went;
'98 Dodge Dakota, paint started flaking in the box 2 years after purchase, tranny had a strange whine/howl that dealer could not identify.
Notice a pattern here!

Best: toss-up between:
'71 Datsun 510, nothing went wrong for over 80,000 miles, until a
friend took it on a one-way drive and a tow truck brought it home. Most fun car I ever drove, shocked many a Big Three car as to it's jump off the line and handling. A great chick-magnet.
'72 Datsun 240Z, almost as much fun as the 510, but better (fantastic) handling, blew many a European and N. A. sports cars away in the twisties. In fact I never could find another car that could beat it.
An even better chick-magnet then the 510, though it was awkward getting more than two chicks in it!

Surprisingly I had very few maintenance issues with it and it was totalled before the frame started to rust!

But, coming up fast in the rear-view mirror:
'08 Honda Fit, over 60,000 km and the car hasn't even burped or farted. Definitely not a "fun" car, but so far damn reliable.