As for stealing:
Assort bits and bobs from stores (I'm absentminded as fuck, I look at something small like a drill bit or screwdriver tip, or even nuts, bolts, washers, etc, then walk out still playing with it and never even thinking about it) Probably about $10 worth in the last 19 years, I've just about always done this, though it's accidental, when I was younger it was green string beans in the supermarket for some reason...
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$16 worth of 4mb 30 pin ram about 4 years ago when I worked at a store. (got canned and almost arrested)
About $2000+ in hardware from the college (they leave a comp open near me and turn their back, it was stripped by the time they turned around, and I was out the door. Also used to raid with my security bit set.) Mainly used to raid the ram, HDD's, NICs, and floppies (I had a comp which ate them like popcorn and swapping my dead ones for good ones was a great and cheap way to replace'em). There were days I'd walk in with a nearly empty backpack, and walk out with it bulging. I also used to raid the dumpsters (technically considered stealing even though grounds and security didn't care as long as I didn't get hurt or get into the trashpactor, used to piss the all holy fuck out of the ITs) (I still don't feel bad about this since I don't think there is such a thing as "stealing" from the government/state, besides, I pay taxes, I may as well use what some of the stuff my taxmoney bought, they just throw the shit out 3 years from now.)
1 tape (Top Gun soundtrack) from an ex-friend, I don't feel bad about this one since he was the main reason I got the FBI at my door last spring.
Crapload of computer screws from friends and stores (again, I don't feel bad, these things add up to like a buck total for the last 10 years...lol, I don't do this one any more, except when it falls under my absentmindedness and I walk off with a handful cause I was playing with'em)
1 P-133 proc from a store I was working at, back when they were still considered decent (highest was the p2-266 at the time) I was scrapping a machine the owner bought from surplus, and I wanted the proc (had a buyer for it) so I bent some pins, left it on the counter just the right way that the owner brushed it and it fell, then he picked it up and grumbled about it being ruined, and I asked if I could have it, he obviously said yeah.
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Though I don't consider it "stealing" (I consider it "liberating" information):
31.82GB mp3's
153 assorted burned proggies.
All of Enterprise season 2 (damn good show, and I'm gonna be pissed if it goes tits up, kinda like I was when I found out Farscape was to be killed)