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Also one thing I forgot. I used to enjoy wargames back in the day.. that is preconfigured buggy blackbox services that you have to exploit in order to progress to the next level. Vortex and PullThePlug used to be some of the really good ones. If someone wants to learn how to exploit software, these games are a really good start.

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I was surprised no one else had mentioned wargames. There are several at http://smashthestack.org/ that cover a wide range of exploits (from simple buffer overflows to format string exploits and md5 collisions). My favorite one was to develop two BF (http://en.wikipedia.org/wiki/Brainfuck) scripts that print out different strings, yet have the same md5 hash.

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