>>83 doesn't work at all for me. No matter what I click on, I keep getting redirected to the "you must be 18" page, and then back to the front page. (Firefox 2 on OS X, and yes, JS is enabled :)

> /channel/5j/freak/834b808bde2c20165692a05a5046e4fce24a01a6

Ugh.
Personally, I enjoy sharing stuff I find on the net with my roommate and friends. I don't think I'd be able to read that filename out loud and know they would get it right.

What I would do, if your goal is a random name that people won't be able to guess, is use a diceware-style naming algorithm. Telling someone "go to blahblah dot com slash monkey golf cube salad polka dot j p g, all one word" is a lot faster than reading off some 40 hex digits -- and then they just get a 404 because they got one digit wrong, and you have to read it again two or three times. If you have a decent sized dictionary, the names can be both short, sufficiently random, and quite readable. (Plus it adds a whole new entertainment aspect to it :)