Gosh, I think my first phone was the Motorola Talkabout which I got in 2001 after finishing high school in PIT and before going away to zal in LA. I think the plan was 350 anytime and 2,150 N&W for $39.99 Got Sprint to give me free data and used to use the text only browser to read 2 lines at a time...
I used to spend hours on hold with Sprint. Eventually I figured out how to keep upgrading my phone for free and switched to the Samsung a400 and then the Samsung a500. I think I also had a Sanyo SCP6000 for a week or so. The a500 was the first pcs vision phone (1xrtt) and one of the first color phones. Also got a VGA camera that plugged into it, but MMS was a bear in those pre-SMS days.
In early 2003 I joined the very small crowd of smartphone users and got the Samsung i330. Great smartphone. FSOD (flashing screen of death) was its main downfall. I became the Palm OS mod on pdaphone.com, which was the main online forum for Samsung Palm phones.
Then came out the great Samsung i500, a wonder of a smartphone in a compact flip-phone. It was awesome.
Samsung was about to release the i550, also a flip Palm phone with an OLED screen way ahead of its time, but Sprint killed it as they wanted to focus on the Treo line. As the Samsung mod, an insider sent me a few i550s to test out that I still have, amazing phones, way ahead of their time.
After Sprint killed it the insider told me that Samsung disbanded their Palm division.
From there I took a brief detour to a non-smartphone (Samsung a900) it was off to Treo land (700p, 755p, Black gen 1 Centro, Green gen 2 Centro) where I've been stuck in neutral ever since 2007 when Sprint decided that my plan wasn't good enough for their cool phones. Then my plan wasn't good enough for them at all so it was off to VZW. Didn't want to pay for a data plan yet so I got a Centro with them as well, but when they announced the end of data I added the unlimited data and hope to get the Galaxy Nexus within the next couple of weeks!