I have 6, not including the Canon 2x TC II. The body is a 10D. Here are the lenses, in order of acquisition...
1. Canon EF 50mm f/1.8 II - wonderful reversed on a G3 and okay reversed on a 28-135/10D for macro photography. My fastest lens, great at night. I don't like the bokeh, so I don't use it when that's important.
2. Canon EF 28-135mm f/3.5-5.6 IS USM - ultimate general purpose lens for me, although I'm using it less and less in favor of my other lenses.
3. Canon EF 20-35mm f/3.5-4.5 USM - a big step on my quest to go wider, and currently my fastest lens from 20-28mm (great, but not fast enough a lot of the time)
4. Canon EF 100mm 1:1 Macro f/2.8 USM - originally bought to photograph slides on a light table (great results, really, but, on balance, I should have waited until getting my film scanner (Nikon LS-4000)). Recently this lens is used less, but is wonderful for flower closeups and sports, if you can manage with the fixed focal length.
5. Sigma 12-24mm f/4.5-5.6 HSM - perhaps the final step on my quest to go wider - wonderful for architecture in tightly packed spaces and landscapes. Interesting and useful as an indoor lens in tight situations (or to enable an interesting perspective on large group photos), but it is fairly slow and often needs flash, unfortunately.
6. Canon EF 70-200mm f/2.8L IS USM - bought about 2 months ago with the intent of doing more sports photography. I haven't done much of that, but it has done an outstanding job when I have used it in this area. Very good for portraits and closeups at botanical gardens, and excellent for some extreme closeup/specialty shots with the 500D (enables tiny DoF). With the 2x TC, I'm happy with its performance for sports when you must be fairly far away.
My next lens will be a fast, wide prime. I've been discussing this with a few friends and have been getting some good advice in another thread here over the last few days. The Canon 24mm f/1.4L is the current front runner, but the Sigma 20mm f/1.8 is a serious contender.
Usually, when I go out shooting (always for pleasure) I take a single lens, but I will put 2 or even 3 in the camera bag in certain situations.
-- Eric