My first phone was... I can't even remember. I know it was a candybar CDMA phone from TELUS — my mom still has it somewhere in my childhood home.
My first real phone was the LG Shine, a variant of the slider phone that was made popular in the Matrix movies (I think). It was one of the first devices to use EDGE for data connectivity, and even supported very low-resolution video calls over the Rogers GSM network, though I never actually made a single video call because no one else had that phone.
I got into smartphones through BlackBerry. I traded in the LG Shine for a Pearl 8100 sometime in early 2008, and loved it so much I waited in line to buy the Bold 9000 the first day it was available. It cost me $800 outright, and I don't think I've ever been so excited to use anything in my entire life. After that, I had a revolving list of BlackBerrys, including the Curve 8900, the Bold 9700, the Bold 9900, and so on.
I got into Android through the HTC Hero, which I was obsessed about. It was white and beautiful and ran this new operating system I'd heard so much about. I followed that up with a Motorola Milestone and a Nexus One, and that was it — I was hooked.
I've owned so many phones that I can't even count. I think my favorite of all time, though, was the HTC Desire Z (AKA the HTC G2 on T-Mobile). I don't know what it was about that phone, but I loved it so much. It had a pretty bad keyboard that I rarely used, and some pretty glaring software issues, but there was just something about it.