What a fun thread.
Eric mentioned the '87 Toyota Camry. That was my first car, a hand-me-down from my sister who had received it from my dad. Had about 130k on it, 5-speed, blue. The car I learned to drive on. It was not fun, not fast (felt like the heaviest flywheel ever), but it was so smooth and so well-built--better than many later Toyotas, IMO.
Cars that have been surprisingly fun:
- My first E28 drive was a revelation. At the time I owned an E36, and I couldn't believe that this older, boxy thing had such great feel through the steering wheel and combined comfort with sharpness so well. That first one I drove had 430,000 miles on the clock and was owned by Dan Patzer north of Seattle. I was hooked, and after spending some time with him learning how to adjust the valves on M10s and M30s, putting new suspensions in 2002s and E12s and E28s, I was hooked. He preferred the E12, but I liked the combination of modernity and old-school feel that the E28 provided. Now I have the 1600-2, which is also fun but a much more limited-use car on today's roads, whereas the E28 is still legit transportation 30 years on. Amazing. But that's not news to anyone here.
- A2 VW GTI: ~2200 lbs, 100 hp, manual steering, no AC. Full-on race mode everywhere without breaking the law. Would lift the inside rear wheel in hard corners. Felt like a daredevil in it, and it was a useful day-to-day car to boot.
- My Ford Fiesta ST is a total riot. I had heard good things about it, but I first drove the car when in Detroit for the wedding of the guy I eventually bought it from. He let me use it for a few days while I was in town, and I just loved ripping around in it. It's the first FWD car that has ever matched the above GTI for fun and feel, despite the slightly numb electric-assist steering. It is almost as fun as a BRZ, but immensely more practical. The specs match up well to an E30 M3: ~2700 lbs, 200 HP, a truly lovely 5-speed manual gearbox with close ratios. But while it is wrong-wheel-drive, the turbo 1.6 makes torque down low so it is a really engaging point-and-squirt machine. Ideal for city driving. The torque steer makes it more fun, but it would benefit from a Quaife diff.
- Cheater answer because I expected it to be good, but it blew away even my high expectations: E82 135i. 2009, 6-speed, modded (tune, intercooler, charge pipe, shocks, springs). Needs a real LSD and better brakes to be a good track car, but on the road it is hard to imagine anything being faster in most situations--and that includes the GT350R. The immense and instant power, on tap in any gear at any time, coupled with a short wheelbase, amazing steering feel (last of the hydraulic systems from BMW), and tires that are big enough to generate big grip without killing the feel and fun make for a car that is easy to push, easy to trust, and just endlessly entertaining. This past weekend, I easily did a section of twisty, hilly, southern Indiana highways that Google Maps predicted to take 50 minutes in 38 minutes--on wet pavement following a light rain. Probably pissed off a few rural residents, because on the way back I saw 2 speed traps on the same route.

I told my dad never to sell that car, even if the N54 is a maintenance nightmare. I don't think BMW will ever build anything quite so engaging again in the modern era. I think the shorter wheelbase and wide track make it much more involving, if ultimately a bit slower, than the E90.
-tammer