#hack on DALnet is constantly bombarded with lame questions. Generally they are "How do I hack hotmail?" and other broad, dumb questions. You've got to look at it this way: If you'd like to pick a lock, you'll have to know how it works first. If you don't understand how the pins inside the lock operate, you'll never be able to pick it. Also, with a little understanding of locks, you can learn how easy it can be to simply drill out the lock core. Of course, someone will notice that instantly....
    So, you want to be a hacker? You first must learn what it takes to be a decent administrator. If you want to hack a web server, you need to setup, configure, and run your own. As you work with the software, mis-configuration holes, cgi vulnerabilities, buffer overruns, and much more will make more sense to you.

Reading:

Read everything you can get your hands on. Once you understand how things work, you can put them to work for you. While there is plenty of information available for free on the Internet, the occasional trip to your local bookstore won't hurt either.

Tools:

Once you understand whats fundamentally going on, the use of these tools will be instructional and fun. I have the files locally, but have links to the author's site so you can get the newest version when it becomes available.