Some of most clever and original sounding music that made me smile broadly -- well, maybe I even laughed once or twice because the music hit a responsive chord -- can be heard on recordings by the Microscopic Sextet, and the Willem Breuker Collective. Both groups play a style of off-center jazz that still has what Stanley Crouch calls "the sound of surprise". For those whose jazz tastes may not be ready for these two groups, you might start with the Dirty Dozen Brass Band.
Music to make you laugh by
No, I don't mean the text of a song as an example. Rather the musical content of a given piece of music, which by listening to it, be it in concert or at home in front of your rig, has made you laugh out loud or grin or smile, because it was funny or amusing in a clever way.