I've been having fun for many years now with Tellme, 1 800 555-TELL (8355). This voice-recognition-based free online assistant was one of the first dotcom businesses I knew about, survived the dotbomb, and seems to be flourishing…
I use the movie listings most often. There's enough voice rec there to get me to an appropriately-timed showing at a nearby theater. The service will give online driving directions, which seem to work pretty well, but which I never really think of using. There's traffic and weather, which should work fine but which I have never used. (Tried them both just now. Weather works great. Traffic works great if you want a full report. It will also let you name a highway, but for the life of me I couldn't get it to recognize "I5" or "Interstate Five".) There's also an amusing blackjack game. While primitive, it does feature a synthesized Sean Connery voice that insults you when you lose.
Perhaps the biggest problem with the service is that the voice rec works only in an extremely quiet environment. Other voices and even noises will almost invariably confuse it. It would also be nice if the service extended beyond straight information to reviews and recommendations ala CitySearch. I'd love to be able to find a nearby decent Thai restaurant using the service, and there doesn't seem to be any technical barrier to such a service.
All in all, though, Tellme has been occasionally useful and always fun to play with. Recommended. (B)
(In case it's not obvious: I am in no way affiliated with Tellme. My only relationship with them is as a mostly-satisfied and highly-amused user of their services.)