Catan

I've never figured out how to win this damn game, but it's a good time regardless.

My strategic sheep monopolies never come to fruition.

This just always turns into a bloodbath around the table. Such a vicious game it can turn friends into enemies...if people are especially competitive. And the luck element is a bit of a drag. Prefer more strategy.

Heh, I didn't know the name had changed. Settlers is a good game, but I played it so much back in the day I played myself out. Now I play it only occasionally when friends call for it. The expansions are okay, but I'm one of the few who feel that adding rules or complexity doesn't necessarily make it a better game or you a better gamer.

late game is just everyone getting 10 cards per turn and it turns into a bit of a clusterfuck

The base game is fun and certainly what started my (still burgeoning) interest in legitimate board games. When I first played it with a regular group of friends, we played waaaayyyy too much and I feel like we more or less exhausted all the possibilities. Luckily the expansion sets add a lot more complexity and variation (including the Game of Thrones edition I just got!)

Simple and fast enough to play with your parents over the holidays. Easy to introduce friends to who are not boardgamers. With the expansions, it can be complex enough for more serious gamers. You can add enough variety to it to make it a quick play online. And the basic concept can be adapted to many iterations and spin-offs. It's the very definition of a gateway game. When I first discovered it, on New Year's Eve 2007, we played all night long.

Loses more and more luster the deeper I get into board games. It's got a place in a board game collection, it's just that place is in the back of the closet away from the things I would want to actually play regularly.

Simple enough that you can pick up the rules as you play, and complex enough that it remains fun game after game. Like any board game it depends on the group you are playing with, but the mechanics are fair and it's a good way to pass an hour.