I agree with Dan. The only Risk I like playing is Castle Risk, which came with a version of Risk a few years ago. I like the continuous layout of the Europe for that game rather than the archipelago style of the entire world. In addition to Settlers, I've heard good things about a game called Puerto Rico.

Some of my friends really get into Blood Bowl, and I played a little bit of Marvel Superheroes when I was younger, but I have a hard time getting into the tabletop RPGs.

I do plan on teaching the youngster how to play chess early on and whipping them mercilessly. Part self-gratification, but in part to have someone to play with.