I had an older brother and I would play 2600 games with him and his best friend. The friend had a way to pirate 2600 games that I still don't understand, but as a result, I got my first experience with classics like Space Invaders, Pac Man, Asteroids and Missile Command on the 2600.
Since I was just as vulnerable as any 5-7 year old to the Chuck-E-Cheese phenomenon, I got sucked into the arcade as soon as I could reach the controls. Glowing, hypnotic images of Dirk the Daring later brought me back into the arcades of Virginia Beach's malls when the newest game was a whopping 75 cents and my parents usually refused to pay.
I whiled away the desperate months after the video game crash with my C64 which was the first computer that I (eventually) had in my own room. Years passed, and I only had inklings through friends of how great the mythical Amiga was. . . I did opt for a NES eventually, but as I got older and was distracted with things like basketball practice, school plays, and AP government tests, I found myself going back to the great games of the 64 - It was still hooked up when I left for college.
I took a break from gaming and was brought back to it (again by my brother) with the advent of 3d exploration and the pointy boobs of Lara Croft. The 'Playstation Era' lasted quite a long time for me and everything after that is not really retro gaming IMO.
A few years ago, I bought a GP2x Wiz from "ThinkGeek" and dug into the forums on GP32x.com. The Wiz reinvigorated my love for classic gaming and sent me on a path of recent collecting that includes a modded Coleco, 2 port 5200, a Sears branded Intellivision, an Odyssey 2, a Vectrex, and a Gensis + Power Base. I'm also a proud owner of the Harmony cart, the 2 Atarimax Ultimate flashcarts, the Ultimate PC interface, the Odyseey 2 233 in 1 flashcart, and the Sean Kelly Multicart for Vectrex.
I'll add a personal top games list here as that seems like a good way to get some rep. These are not in order but are listed chronologically. There is only one 2600 game on the list, but I really learned to play video games on the VCS. I can remember reading and studying the manual for Combat, Space Invaders, and Championship Soccer (6 year olds like fireworks), choosing the various game options and starting to control my own gaming experience. I've really never looked back ever since.
Superstar Ice Hockey C64
The Legend of Zelda NES
Wing Commander PC
Tomb Raider PS1
Resident Evil PS1
Madden NFL 200x PS1
God of War PS2
Mass Effect 360