1st Place- 1991 Honda Accord
Bought it with the odometer inoperable (it had stopped at 282k) for $1,500. Drove it for 6 years with multiple 2,000 mile road trips and the only thing it required in the time outside of routine stuff was replacing pulley which had let go on me about 1/4 mile from my house and ripped the belt to shreds. Pushed it home, picked up the parts I needed, and it was back on the road in under 30 minutes. Sold it for $600 in 2012 and as far as I know, it's still on the road (we last saw it in November of last year).
2nd Place- 1997 Grand Cherokee (4.0)
This Jeep wasn't without some issues- all of which are comically common to the ZJ. It had electrical issues which caused the Vehicle Information Display to go haywire from time to time, it was leaking from the oil filter adapter (never had to top off, just left little annoying drips), and the headliner was sagging something fierce. However, it never left me stranded or failed to start for me and that 4.0 was a fuel thirsty tank of an engine. I toyed with putting this first, and in the past I've stated that this is my most reliable vehicle, but I couldn't this time because I've realized that it had more flaws than I like to remember- they were just minor enough for me to not have to fix it as they never effected daily drivability.