Check ign.com for some controller reviews.
I would recommend 1st party controllers in general, I've tried several 3rd party controllers for other systems and they just don't act right, like when I press right my character on screen will jerk to left first then right. For that reason I've been staying away from 3rd party controllers, both of my PS2 controllers are Sony.
However, I did get a "Microcon" for Gamecube (4 1st party controllers are just too much), and it's behaving nicely so far. "Microcon" controllers are made by MadCatz, there is one version for each of the 3 major systems, and they all have received pretty favorable reviews on ign. "Microcon" for PS2 is selling for $15 at BestBuy last time I was there. While I was there I put my hands on the "Chameleon" controller, and I have to say it feels great, very very comfortable. I dunno how it performs, but it's the most ergonomic one.
As for games, you can't really go wrong with the "Greatest Hit" titles (those with a red band on top of the cover), they are not new releases and are < $20.
Hope that helps.