Of all the diabolically creative alarm clocks in existence, this new app called TalkO'Clock is close to the top of the heap. The idea is that through an anonymous P2P service, you can request wake-up calls from totally random strangers. Yeah, this will end well.
To be a part of what is surely going to be a epic (if short-lived) level of shenanigans, just sign up for free at the TalkO'Clock website. Set yourself a few alarms, and pick whether you'd like to receive a call from a male, a female or a robot who may or may not be transgender. At the appointed time, TalkO'Clock will choose a name at random from a database of available callers, call them and then anonymously connect them to you. They are encouraged to wake you up "creatively."
On the other end of things, you can register to be a wake-up service just as easily, and if for whatever reason TalkO'Clock can't find someone to be a waker, the wakee gets a call from a robot instead. This is all free, although there must be some kind of revenue generator down the line somewhere, and TalkO'Clock swears up and down that your phone number is perfectly safe with them. Privacy issues aside, a service like this can certainly be abused six ways to Sunday, but in any case, it seems likely that you'll end up very much awake if you decide to take advantage of it.