I had this awesome book full of BASIC games for the Commodore 64. It ruled.
Mastering Amiga Assembler
Teach Yourself C in 24 Hours (all of the Teach Yourself * in 24 Hours books are embarrassing, though not as embarrassing as "For Dummies" books).
Ooh...No, I've got it: I took the TCP/IP portion of the MCSE exams, and I had a study guide for that. That's the most embarrassing (because it indicates I took an MCSE exam...but, there were dark times in IT before most of you were born...many servers ran this OS named Windows NT, instead of UNIX or Linux).
The moment when I typed something in notepad and it opened in IE I was running all over the house screaming "IT WORKED!."
I had that same experience with HTML, I'm sure if I could've viewed source on a load of decent Python programs I would've gone nuts for it as a kid. A hell of an improvement to feeding a book full of BASIC into a C64. If the rest goes to plan, there'll be a lot of handy hackers around in a few years.
Also "Learn Java" (1996) and "Enterprise Java Beans" (2000).
Also, "The Road Ahead" by BillG. From my aunt.
I should make up some story about finding it in a dumpster or buying it for $2 at a garage sale or something, but whatever.