Chess: This is the first tabletop wargame most people can say they have played as a child or an adult, and for many it is the only one. For me it was more then that, it was a training tool used by my father to teach me, to hone me, and better yet to guide me. When I was younger I had a bad attitude, I struck out at those around me, and myself often enough. My dad kept sitting me down to play chess with him, but not in a calming easy game as you would think. He taunted me, he lured me into mistakes, he pushed ever button he could in order to make me angry and lose my focus. I remember him sitting me down after I tried to get up and walk away from the game. He said some of the most important words I still hold close to my heart. "You are never going to win if you don't stay focused on your objective. You let others goad you, and you are just letting them win." Granted, when I was younger I didn't care what he said, nor did I truly understand what he was telling me. Now though, I look back and thank him for that lesson, among many others.
Dragonlance: The 5th Age: This was my first RPG kit I ever personally owned, and it really was the first time I ever actually played as a dungeon master. It really helped me learn just how players thought, how my personal characters would be misused in the story, and how to actually tell a story. Of course I was still only in high school, so of course my stories still sucked compared to what I can come up with today, but they were at least solid and made sense as needed.
Mage: The Sorcerer's Crusade: This RPG really helped me figure out what type of theme I enjoyed with games. With Dragonlance I more or less stuck with the high fantasy of that storyline, but with Mage I was able to play a bit more so I went a bit darker and more gothic. To this day I still enjoy low fantasy, and tend to have my minis darker toned, and stories more gritty. At the same time I still kept a sick sense of humor in the games. One particular moment where I had the players trapped in a cursed church, and the dice rolls just hated them. Everything they did managed to crit fail and had people being flung to low and slamming into window seals and knocking themselves out, or even worse. Eventually I had to use a couple of my custom characters to save them out of pity. In the end though everyone laughed at how bad the simply church was beating them without me even needing to add enemies to fight.
Warmaster: Honestly, this is the game I played most with my then girlfriend (and now wife). I think this is what got her into wargaming, and as such lead into her and I getting Warhammer 40K armies to fight against each other and then gaming together since then.
WarmaHordes/Anima Tactics: I coupled these together, because at the end of the day I learned the same thing from both even though I wanted to enjoy both. I simply don't like playing with premade characters, especially powerful premade characters. In all my time of playing Warhammer, Warhammer 40K, and various other games I never used special characters, then I go to Anima Tactics and found it to be nothing but special characters. it rather took the enjoyment out of the game since I couldn't grow any real attachment to them. Same thing with WarmHordes, as I simply didn't care for the fact that my main guy was set in stone with background, gear, name, and everything else I would want. As special characters became more saturated in the Warhammer worlds, I found myself less inclined to go back to those games as well.
Heavy Gear Blitz: I don't like painting miniatures... at all. Yet when it came to HGB I found myself enthralled with the minis. I couldn't wait to get things finished, and for the first time in many years I actually had a fully painted and table ready army. That wasn't it though, after I was done with my PRDF, I actually found myself wanting to buy more armies to give me more to play with and to paint. HGB really seemed to light a fire in me for the overall hobby, a fire that had been pretty dim for a good number of years prior.
Warhammer Fantasy Roleplay: The game that made the Dark gothic world with dark humor for me. The first edition is still the best as far as I am concerned, but I have owned each addition to the current third just out of thewant to keep up with the world I enjoyed so much. While GW might be going more 'grimdark', the WFRP world always had just the right challenge and darkness to it to give players and the narrator a feeling of wanting to return to a personal level and not just a battlefield commander level. Would love to get in more games, but alas no one nearby to actually game with.