[Iced Tea]

I liked Underwood's answers the most.

Software:
Photoshop
It's pretty much the only art program I use aside from MS Paint. I started with Photoshop 5 in high school and have worked my way up to CS5 Extended. I've found this line of product excellent to do all of my digital art with. It's very versatile once you get to know it.
Pros: Industry-standard software. You can also make animated .gif and transparent .png images with it. CS2 is free from Adobe now. Now you, too, can art like the pros!
Cons: Expensive, if you want to be legit and buy a newer version. CS2 does not have the (really handy) Rotate Canvas feature that later versions have.

Tablet:
Wacom Graphire 2 ET-0405A-U0K
4"x6" active area, it's my very first drawing tablet which I bought secondhand off Ebay for $60CDN including shipping, years and years ago. I've never had to replace the pen / nib / protective cover, and it's been on two trips to and from Taiwan with me.
Pros: STILL WORKS WITH WINDOWS 7. Just get the driver for Graphire 2 for Windows Vista. Which means if there's more of these being sold online, chances are they'll be going really cheap and you'll get yourself a good tablet for a good price.
Cons: I guess some folks wouldn't like the tiny active area. And replacement parts / repair might not be possible because it's so old?

Paper (sketchbook):
Hardcover, coiled, perforated removable pages, 8.5"x11" 70lb thickness, white.
Pros: DeSerres (prebviously Loomis Art Store) had its own brand of these which made them relatively inexpensive.
Cons: They got discontinued and replaced by a product of much more inferior quality, to my great distress. Sketchbooks of these specs don't really exist. Haven't searched online yet because I do mostly digital now anyway.

[Wubble]

Software
Painter X2 12
Corel's latest in the Painter series, a pure painting software
Pros: A lot of brushes, drawing and painting feels natural, canvas rotation and many other features to keep you happy.
Cons: Because it's designed to be a painting software, it's text editor is very basic. Sometimes slow, rare crashes.

Tablet
Wacom Intuos 4 L
Wacom's professional-line tablets with multiple tips
Pros: Awesome feel, large surface area, many buttons and enough pressure levels to share.
Cons: Tips cost, as does everything else with it.

Pencil
Pentel Click 0.5mm
A mechanical pencil with a long eraser at the end, 'sideclick' mechanism allows faster drawing.
Pros: Feels good in hand, variety of colors to differentiate lead types
Cons: Sometimes the eraser twist isn't tight enough and it slips

[Flutterbyes]

ART TOOLS MASTERLIST THREAD, I GIVE THEE LIFE. LIIIIIIIIIFE!!!!

... that's what Shen told me to do, at least, when I brought up a Void database of digital and analog art materials where one could easily look up reviews and examples of things from Voiders (and not have to guess at what the needs and skills of, say, Amazon reviewers are).

But, it looks like the convenience links in the masterlist post are all broken, so maybe we should start over?

Also, maybe we could make a separate list of "Cheapies but Goodies" for analog and digital supplies, since those can be a real lifesaver (like these nylon brushes from Ikea).