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That would be my eTim RGB Modded NES Toploader. I have a PCEngine and SMS as well, but the NES is the oldest system I have (if you ignore that the Toploader came out in the 90s). I just got a Commedore Vic system, but that's not as old as the Commedore 64.

As for why it keeps me coming back? It just has so many hidden gems that most gamers don't really know about. Mario, Castlevania, and Contra are just the tip of the iceberg. There's over 100 solid games for the system and the two button gameplay just works.

Recommended games for it are...

Adventure Island 3
Adventures of Lolo 1-3
Baseball Stars
Battletoads
Bionic Commando
Master Blaster
Bucky O'Hare
Burai Fighter
Castlevania 3
Clash at Demonhead
Conquest of the Crystal Palace
Contra & Super C
Crystalis
Darkwing Duck
Double Dragon II
Dragon Warrior 3 & 4
Gargoyle's Quest II
Guerilla War
Gun Nac
Isolated Warrior
Journey to Silius
Kabuki Quantum Fighter
Kirby's Adventure
Zelda
Long Ranger
Megaman 2
Metal Storm
Mike Tyson's Punch Out
Ninja Gaiden 1-2
River City Ransom
Shadow of the Ninja
Shatterhand
Star Tropics
Mario 3
Turtles III
Terra Cresta
The Guardian Legend
Tiny Toon Adventures
Ultima Quest of the Avatar
Vice Project Doom
Zen Intergalactic Ninja

^All of those games play just as well as any modern indie. I avoided the acquired taste games in my collection.