History over 11 years (I mostly only changed phones at contract renewal time).
First the dumbphones:
Motorola MicroTAC 650 (big black "flip" phone) originally with CenturyTel, then bought by Alltel
Nokia 5165 (freebie from US Cellular)
Motorola v60i (back to Alltel. I still think this is the best pure PHONE I've ever had from a reliability/signal/call quality standpoint).
While I had the v60i, I also had first a Handspring Treo 90 PDA, then a Palm Tungsten C PDA (best pure PDA ever). I used a data cable to connect them to my v60i to create a "two-piece" smartphone at blistering 1x speeds.
Then, I moved to the smartphone world:
HTC PPC-6700 (Alltel, quirky at best, better with custom ROM)
HTC PPC-6800 (Alltel, I custom ROMed the crap out of this one)
HTC Touch Pro (Alltel, kept stock ROM)
And now the Incredible. And so far it's living up to its name.