Okay, I've got some time to think about it, so here goes:
'49 Chev (never registered - I just w*rked on it to learn during my teens)
'54 Desoto (never registered - same deal as Chev.)
'66 Olds F-85 (University graduation present from dad.)
'69 Corvette (new)
'72 Opal Rallye (new)
'74 Mazda RX2 (Wankel) (new)
'77 Datsun B210 (new)
'82 Toyota Tercel (new)
'81 Olds Omega (dad's last car I bought for $600)
'91 Mazda 626 (new)
'01 Chrysler Voyager (new - for DW)
'99 Honda CRV
'00 Mazda 626 (a Ford, built by UAW in reality)
'00 Buick LeSabre
'12 Toyota Rav4
My figures are not completely accurate, but by my best accounting, I have spent a total of $83,000 total to purchase all 15 cars. I don't know what that would come out to in today's dollars (much more - I'm certain.) For instance, the new Corvette cost $5K and so did the used '00 Buick when I bought it in '12! Heh, heh, this could be in the inflation thread(s) but I'll just leave it at that since YMMV.
I've never "traded" a car for another. I've simply junked the old car or sold it outright to someone else. In theory, the $83K figure needs to be reduced by a few $K to account for selling the old cars, but I don't recall the figures. One car was totaled by the insurance co. following an accident.
I haven't included my dad's cars that he let me use between the time I started driving until I bought my first (real) car at 23. This has been an interesting trip down memory lane.