Not sure if you mean the original gameboy or not but the sims bustin out for gameboy advanced is pretty fun if you're into the sims
If not then all I can suggest is PC stuff, which is as follows:
- Terraria - Low specs, potentially endless game but you could set certain challenges maybe
- Orcs Must Die! (or Orcs Must Die 2 which is coming out soon, so you could jump on that bandwagon) - Don't think it's too demanding in terms of specs and isn't overwhelmingly long
- L.A. Noire - I think this one might be a bit demanding on your PC but its a pretty interesting game, could create some fun moments for commentary
Can't really think of anything else that's remotely short since I play games that are very very long lol, if I think of anything else I'll let you know