1. Sega Channel
I lived in a small town in Ohio as a young lad, but for whatever reason our cable provider had the Sega Channel. Even more amazing was the fact that my parents were willing to pay the $15/month for access. I remember the day the UPS guy delivered the massive Sega Channel cartridge to my house; it was nearly as large as the Genesis itself. Over the next several months of the Sega Channel's existence, I grew to love the loading screen music. It was a sad day for me when the Sega Channel came to an end. It was ahead of its time, and I still believe that it is the future.
2. The Legend of Zelda: Link's Awakening DX
In the year 1998, I purchased a GameBoy Color from eBay. It was the first purchase I made, and I did it at age 17. A friend loaned me his copy of Link's Awakening. I played the game several times over, and in the end I collected all of the photographs and even got the special ending for not dying. To this day Link's Awakening remains my favorite Zelda game.
On 9/9/99 I became one of the lucky few to own the Dreamcast. I spent a lot of time playing Crazy Taxi with friends, as we all tried to beat one another's times. Shenmue indoctrinated me as a Dreamcast fan for life. The console supported online play as well as web browsing. It was truly a system a decade ahead of the curve.