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.
2. 1991 Bridgestone RB-1
Another Bridgestone, I picked this one up used after I moved to Ohio. Rode nice, but I got the Gunnar soon after that I liked better.
3. 1999 Gunnar Crosshairs
(my first S24O!)
4. On One Il Pompino
I was riding my Gunnar around quite a bit as a single speed, using a 39x15 magic gear, but I wanted a dedicated single speed rig. I bought and quickly sold this Il Pomp. I'm not sure why I didn't care for it. Maybe the track ends?
5. Iron Horse Excelsior
I got an urge for a modern road bike, so I picked this up cheap from Nashbar. It actually rode very well--maybe due to the carbon seatstays, and I liked the STI shifting. But, the tire clearance was limited to maybe 25mm, and I found myself pulling my fixed gear Gunnar out for most of my road rides, so off it went.
6. Rivendell Romulus
7. Salsa Casseroll #1
This should've been a great bike: fattish tire clearance, low bb, single speed or geared dropouts. Somehow, it just never came together for me.
8. Scattante XRL
I gave this a try, with an image to build a real racing 'cross bike. I didn't like it, so I abused Performance's 100% satisfaction policy and returned it.
9. Singular Peregrine
Should this be classified with the 29ers or the road bikes? I didn't do much off roading on it, so maybe it should go here.
10. Surly Cross Check
This bike has its own page here.
11. Giant TCX
I actually raced this one in a few CapCity 'cross events, carrying me to multiple glorious mid pack finishes in the men's C division. Finally, I decided I didn't like riding around in grassy circles all that much.
12. Salsa Casseroll #2
Picked up on clearance from Speedgoat. Whatever didn't work for me on the first Cass... still didn't work here.
13. Surly Pacer
I love that Pacer baby blue, so when I found one in a 62cm for sale, I jumped at it. But, it really didn't do anything better than my CC, and the CC wins on tire clearance and single speedability.
14. Specialized Tricross Expert
I've always like the looks of the Tricross, but worried that even the largest size was too small. Turns out, I was right to be worried.
15. Fuji S-10-S Ltd
(as I got it off CL)
(after I modified it)
After reading Bicycle Quarterly for a while, I was curious to try a low trail bike. When I found this Fuji for sale locally, I gave it a go. I liked the low trail, I liked the skinny, flexible tubing, but I didn't care for the tight tire clearance or high bottom bracket with 700x35mm tires mounted.
16. Rawland rSogn
More about this bike here.
17. Soma Double Cross
18. Rawland Nordavinden
19. Specialized Globe Vienna 1
Yep, another link.
20. Novara Buzz One
One more link.
Need to add: Trek 620, Velo Orange Camargue
Cross Check Triumphant
So after 20 bikes, the only two still in my stable are the CC and the Buzz (and the Buzz is half heartedly for sale) The Crosscheck has such a powerful combination of smart design, low price, and versatility, that it's hard for any other bike to supplant it... even for a serial bike flipper like me.