First of all, I love my Corrados (I have to say that, since the black one may be listening).
Coolest to me? 1979 BMW 323i.
I was trying to import grey market cars to finish paying for college (I failed..), but after driving this one, I told the guy asking me to find one that I couldn't find anything. I hid it away for about a month, but he got really pissed when he saw me on the street in it ("..dude, this market moves quick! I thought you weren't interested anymore!.."). It was a small Southern town, you can't hide much of anything for very long..
Got it about 1983 or so, when BMW had just been discovered by the "yuppies". The streets were full of US market E21s, wheezing along with smogged M10 engines dragging full leather interiors, rubberbabybuggybumpers, and a ton of power "luxury" crap as well.
It was like my 2002 on cocaine (we didn't have Meth back then). Power, handling, and lightness. It was a chick magnet on the outside, since girls back then thought it was just another 320i with a rich guy in it. They were disappointed by the inside, since it had cloth seats and the original European AM/FM monophonic/medium wave radio. I'm not advocating getting weird on the street, but I have to admit that I made a lot of the local guys in new 3rd gen Camaros & Firebirds, and Fox chassis Mustangs scratch their heads and wonder WTBerkeley just happened to them..especially on the curvy 2-lanes at night (halogen lights weren't exactly legal yet in the US back then).
I lost her one rainy morning after I moved to Atlanta. I guess about Spring 1987 or so, I was headed to Road Atlanta to work corners, and some clown knocked me into the wall in the median of I-85 N. Didn't help that I was just about broke, and was running SCCA Spec Racer (Renault, back then) takeoff Goodyear Eagles on it. That was also the morning I joined the "Roof Drivers' Club".
EDIT: Forgot to mention it was raining. Shaved tires with a few heat cycles were probably not the best thing for that, especially in an E21 with decent power.
I ended up letting it go to a BMW buddy of mine back in Mississippi (the small Southern town I mentioned previously), he took the sweet little M20 and rear discs out of it, and put them into his wife's US market E21. I've lost contact with the guy, don't know whether it's still running around or not.
It doesn't happen as often as it used to, but I still have dreams about that car from time to time..