My greatest gaming moment had to be a few years ago when my extended family was over for a family party. A bunch of the kids were around including the "What's an Atari? Can it connect to my smartphone?" generation. I had pulled out my old NES a few weeks earlier for some classic gaming. It was still out with a pile of cartridges sitting next to it. The kids saw it and got curious, so I grabbed a multiplayer racing game off the cartridge stack and pulled it in.
At first, they were bored by the whole experience, but then they started getting into it and fighting over the controllers for who got to go next. By the end of the night they gone through four or five of my old multiplayer games, including a good hour of head-to-head Duck Hunt. It was just great watching all the millennial having so much fun with my old, dusty NES like it was any other modern system.