Update: hardtail 26ers here.
My road riding started on my pop's hand me down Schwinn. Typical early 70s bike boom, with Ashtabula cranks, steel rims, etc. But I'll start this history with the first road bike I actually bought:
1. 1991 Bridgestone RB-T
(not my bike pictured). I was heavily influenced by reading Grant Petersen's Bridgestone catalogues throughout college, so when I went road bike shopping, a quick spin to the Bike Gallery and this RB-T was mine. Must've been the summer between my freshman and sophomore years at the University of Washington. The Suntour drivetrain never shifted very well, but otherwise this was a great bike: good clearances, a nice frame, good geo. They're actually still quite in demand today, and I wouldn't mind finding one now. Mine was a 59cm, probably too small for me, though.