Hmmm. I have many that I'd consider the benchmark of their individual genres, but I'll just list a few here:
Forza 3/4 - For me, these games changed everything about sim racers due to their accessibility. Having the rewind feature, autobraking, and the brake guide all helped me overcome low vision problems I typically have with games like these. It doesn't hurt that they're a hell of a lot of fun.
Quest for Glroy 1 & 4 - Quest for Glory 1 introduced me to the fantasy genre across all mediums, something I still deeply enjoy today. It was also among my first PC games, and along with Leisure Suit Larry 2, would come to define the adventure genre for me in a lot of ways. Quest for Glory IV took the premise and the promise of the first few games, and blew them out of the water. It was buggy as hell, but it became the shining example of the adventure RPG for me.
Elder Scrolls III - Although far surpassed in regards to quality and fun, this was my first Bethesda game and I've been in love with their take on the RPG ever since.
Final Fantasy VII - Although I believe the game to have been mechanically surpassed by now, it is still the benchmark I hold all JRPG's up against. This game changed me from a mild, occasional gamer to a full-blown addict almost literally overnight.
F-19 Stealth Fighter - My first flight sim, and still one of my favorites. If my Tandy ran, I'd probably still play this even today.
Pirates! - The original was my introduction to a sandbox-type game. I was given little information to go on besides, "Here's who you're allied with, here's the last sighting of X, here's a ship, go have fun!" And that's precisely what I did. I think it was essentially surpassed by its remake on the Xbox and other platforms, but the addition of cartoony mini-games didn't help it much.