Is there any way to get the original Fallout and Fallout 2 working on a Mac?

I personally attempted this a while back. I ended up buying the actual Mac version of the game:

http://www.amazon.com/s/?url=search-alias%3Daps&field-keywords=fallout+mac

As of November 2012, GOG started offering the games in Mac format. Both Fallout 1 and Fallout 2 were offered. This was probably be the best/most affordable way to get the games. Fallout Mac CDROMs on Amazon seem way much overpriced (due to their scarcity I assume).

Update 1/1/2014: Unfortunatelly GOG has removed all Fallout games from their catalog. As discussed on reddit this is probably due to Interplay's publishing rights on the franchise expiring. The games are now only available for download to those who have already purchased them. The games have also been removed from Steam and it is unclear whether/when a new distribution agreement will be made with Bethesda, who now holds the publishing rights.

Try installing WineBottler http://winebottler.kronenberg.org/. It's a nice frontend for Wine (which it brings with) and can package your game into a nice little .app.

FWIW, I was able to run Fallout with it. Didn't try Fallout 2, though.