Here's a little script that will open a random playlist from Webjay. Set it to run at a certain time every morning (with a crontab addition like: 0 8 * * 1,2,3,4,5 /usr/local/bin/perl /Users/yourname/documents/webjay.pl ) and it makes a handy radio alarm clock.
Be careful though, if you really need to wake up: SMIL playlists won't play in RealPlayer v<10 if they use progressive jpegs. You could change the .smil to .m3u, but then you're in danger of oversleeping if it picks a playlist that only contains videos.