Play Windows games on OS X
I'd recommend WineBottler; I have about 30 apps and games that work great with Wine. A few pointers though:


Check the Wine Application Database for various apps. This shows what version of Wine, what winetricks you need and what workarounds may be required.

Disclaimer: I'm a super maintainer
Check the official system requirements for the program/game. For older games, this will state which version of .NET or other framework is required—make sure you select the same version in WineBottler to be installed in the new prefix.
For programs that don't work, you can create a blank prefix with various frameworks installed and try combinations of winetricks without needing a new prefix each time.