"Crazy" to me is a very relevant term...
As a composer for media, most of the time I don't get to do alot of crazy things, but I do have some time to make my own music.
I have written some progressive jazz pieces that have two or three different time signatures going on at the same time, as well as band members playing on different scales at the same time...
Maybe I have some recording of my old band playing some of those pieces if you're interested.
Apart from the jazz scene (where it's a lot easier to get away with "crazy"), in my concert music I've tried to bring "crazy" onto the stage now and again, most of the time it went rather well.
I don't think I've ever done anything that no one has done before, but I've had those moments when you just go "I'm writing that dissonance in and I don't care if the audience hates it", because it's what I wanted to do with the music.
So, few dissonants, few odd-meters, few strange performance instructions (for example, all the woodwinds section got percussion scores - and had to open and close their instrument buttons in time, the lead violinist got a jazzy chart with nothing but harmony and the suggestion to improvise a winter day, etc...)
Omri.