My first buffer overflow exploit: pretty easy
jvns.ca
jvns.ca
[2] http://www.phrack.com/issues.html?issue=49&id=14#article
You can read it for the cult value and as a general reference to have, but for someone really looking to get into it, I'd recommend Corelan's exploit tutorials, Open Security Training's courses and The Legend of Random's articles on reverse engineering.
Corelan's exploit tutorials @ https://www.corelan.be/index.php/2009/07/19/exploit-writing-...
Open Security Training @ http://opensecuritytraining.info/
The Legend of Random @ http://www.thelegendofrandom.com/blog/
I really liked the hash-maze, cool idea.
like WestCoastJustin pointed out phrack has phenomenal articles but require you to have a fairly strong understanding of C and Operating system type things.
Smashthestack and overthewire both have a wide variety of wargames that might be fun to look into if you're interested in pursing security related challenges:
smashthestack - http://www.smashthestack.org/ overthewire - http://www.overthewire.org/wargames/
There's also an intro level CTF going on for another 9 days @ http://zeromutarts.de/
Registration is easy and instantaneous.