This is not a list of games to own. This is mostly a list of games that changed my perception of games in one way or another. It's also sort of a progression of gaming for me. It's probably not unique from anyone else here. Or maybe it is...who knows.
1. Monopoly - This was probably my first foray into more mature games. I remember playing this while camping with my friend. I also played this for a couple of summers into high school with another group of friends. Didn't really play it much since then though but it does have a fond place in my heart. Contrary to popular opinion, this game does have some strategy.
2. Risk - This was my first foray into a game with conquest and some degree of diplomacy remembering the famous North Africa - Brazil treaty only to watch it become worth less than the paper it would have been printed on. Played this one for many summers up into college. It of course got supplanted by other games.
3. Dungeons and Dragons - Like many other people here, this was my first introduction into role playing. Fun game and I remember many late nights playing this. Sadly, not too many of my friends are interested in playing.
4. Axis and Allies - For me this was the game changer. Like Risk it was a conquest game. Unlike Risk, you had different units and different attack values. The territories had different values, so you weren't just willy nilly attacking territories, you were trying to maximize your income. No diplomacy (unless it was amongst your allies). I still enjoy this game quite a bit. Unfortunately, one of the members of my group of regulars is not suited to playing it (he's Mr. Armored assualt).
5. Firefight - This was my first foray into wargaming. Unfortunately, I didn't have many friends that would play it with me. Fortunately, it was simple enough that you could play it solo.
6. Squad Leader - Didn't play this one too much but played it enough to know that it took what I learned playing Firefight to a whole new level. I never bought a copy of my own.
7. Star Wars - The Roleplaying Game - This was the roleplaying game I enjoyed the most. It made roleplaying simple and fun. Didn't too bogged down in rules.
8. Magic - I remember some friends bringing back some of the betas from Gen Con and we ended up playing the hell out of it when the unlimiteds came around. It fell out of flavor a couple years later.
9. Settlers - After a hiatus from gaming for a while, this was the game that brought me back to gaming. It had screwage, trading and a bunch of other things. There is enough randomness that each games feels different from the last but the randomness is mitigable enough that you don't feel hosed all the time.
10. Iron Dragon - I know this isn't the first of the Empire Builder series, but this was the first one that I played. It actually feels like running a railroad because you have to lay down track and make deliveries. Sometimes the game can drag on but it's fun enough.
11. Puerto Rico - My first foray into the less random Euros. It is a fun game sometimes but the lack of randomness seems to make the game feel the same after a while.
12. Caylus - My first foray into the "I'm gonna screw you by putting my stuff here" games. I like it enough but none of my friends do, so we don't play it much. I can see why they don't like it. it not the same type of screwage as, "Ah ha, Mr. MX....Oh yeah...well since you wiped me out, I'm firing evertying I got at you".
13. Nuclear War - Speaking of which. This was my first introduction to the "take that" game. Disturbing theme but fun nonetheless. I love the ability to retaliate if you get wiped out with nukes which leads to the possiblity that noone will win.
14. Tales of the Arabian Nights - First game I remember where I didn't care so much about winning or losing but having the journey.
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