Saw a geeklist that got me thinking about games that I have played over 100 times. Here's what I came up with...
ChessCanastaAcquireBattleshipCarcassoneRiskDon't Break The IceEuchreSettlers of CatanStar Fleet BattlesMonopoly
Chess: Probably my number one game all-time. It has to be one of the first games I ever learned. It was certainly the one I took seriously - I bought a couple of books on the game before I was in my teens, and was able to beat all-comers in grade school.
Star Fleet Battles: Devoted several years to this one game, back from 1985 to about 1991 it was the game I played the most. My dear friend Mark Hamilton (who passed away in 1999) and my brother Tab played this one extensively. Our greatest battle was a 12 hour slugfest against a B10. I'll have to tell this story sometime.
Canasta: 90% of my games were against my grandfather, David Barlowe who passed away in 1985. We Tab and I visited him in Florida, grandpa and I played hour after hour of two-handed. I remember two trips where 50% of our time there was spent on Canasta. Solid way to spend time with a friend. Mom and Dad used to play Dave and Opal 4-player, and usually the girls won. Grayson and I recently began playing Canasta Caliente, introducing the game to the next generation...
Acquire: Sid Sackson classic. I've played easily over 50 games face to face, against a variety of people. Was my second German game (although I didn't know it at the time), the first being Kremlin. Bob Oberheu introduced my brother and I to this one, our cousins had been playing it for years before our first game in 1985(?). Online I've played over 100 games easily during the summer of 2004. Haven't played much since, a little dry compared to the new German games out there today.
Carcassone: Mostly have played this with Grayson. We have tried most of the expansions, he enjoys the first (Inns and Cathedrals) due to the "triple effect" of two of the tiles in that set. He's always trying to break the record on points scored on the triple, which is easily over 100 (although I think he still lost that game to me, he didn't care, because he got his name written in the back of the box!).
Risk: I remember breaking this out after we had moved to Toledo from Temperance, Michigan in about 1978. My dad had owned in since probably before I was born (1960's). I think it was Tab, Dad and myself. I remember being fixiated on the black colors. Before Risk all we had ever played was "Go Fish", "Crazy 8's", Chess, Break the Ice, possibly Life and Monopoly. Perhaps Feudal and Jumpin' (3m, later Avalon Hill games). Risk was so totally unlike any of those games, it was a bridge game that I would attempt to jump Starship Troopers (AH) and UFO shortly after. Risk was the game that I usually used to break in a new group of friends. For a while Acquire took on that role, nowadays it's usually Settlers of Catan.
Don't Break The Ice: this cute little game I had as a small boy, and I purchased a copy for Grayson a few years ago. Gabriel now gets a kick out of it. My only caveat is that it is a pain to set up, and the dexterity required from a child to set it up usually means that the child is too old to play the game.
Euchre: Played this 4-player 5 card game almost exclusively during school hours at study hall and the independant study group I was in during my Junior and Senior years (1985-86). The jacks are the high cards, called bowers. Played hundreds and hundreds of games, and eventually taught it to my parents and grandparents. I've never really played it much since the late 1980's. Noone at Watchtower Farms had heard of the game when I was there from 1992-94, the game there was the very similar (and superior) Spades, and I've rarely met someone since who's even heard for Euchre. According to some reviews on the web, the game orignated on ships that sailed the great lakes, and it's a midwestern game, which would explain this. In Northeast PA the big game is Pinochle. Part of the appeal of Euchre played in school was how loud it was played, banging on the table when tricks were taken, or game was made. Sometimes cheating was encouraged, and it was part of the game to steal the deal from the opponents, and attempt to ignore the suit played to dump losing cards, etc.
Settlers: I first remember seeing this game at Mind Games in Toledo, late 2000. If I remember, I searched online for a review before I bought it, and may have stumbled upon the 'Geek at that time. I purchased a copy shortly after seeing the favorable reviews, and this single purchased has caused what you are reading here. I have since purchased probably over 100 different games, mostly German. I've played Settlers face to face probably close to 50 times, which is certainly more than any game I've played since. If you count online, it's the most I've played anything since the 2-3 period I was playing Star Fleet Battles very heavily. I've played around 30 tmes on Brettspeilwelt.de, and over 150 on Microsoft's Zone.com. Settlers is usually the game I use to introduce new people to the boardgaming hobby.
I have kind of burned out on Settlers. I own most of the expansions, including the book. After so many plays it has little mystery left, and I can do very well even in 4-player games unless the opponents are very experienced. Online has kept the game alive to a degree, as with enough games you can get some unusually patterns, and the games go quickly. I can usually play while surfing the web inside another window and still do well.
(What games have YOU played over 100 times? Post comments below!)