DavidBuchanan: Wow. What a great community of gamers and fellow nerds. Thanks for the links and stuff. Super helpful guys.
The wineskin site has no games itself to download correct? Just the wineskin mod itself?
Wineskin isn't a mod; it's a Mac app that is a wrapper for WINE, just like CrossOver. Like CrossOver, you use it to create a compatibility wrapper in which you install and run your Windows games.
crazy_dave linked to my tutorials on how to use CrossOver and Wineskin; I've also been writing a semi-regular column for Inside Mac Games called "Crossing Over", focusing on getting GOG's titles to run on OS X through CrossOver (but the same principles apply to Wineskin, and I've been working on a write-up about Wineskin for some time now).
If you're more content to use premade wrappers, PaulTheTall (who crazy_dave linked to) has a whole ton of wrappers, and if you go to the Porting Team forums, you can also download wrappers too. Remember, these are just the compatibility wrappers, powered by WINE - you still need to (legally) get copies of your Windows games, and install them (assuming they work in WINE).