I have in the past experimented in a big way with makeup (though unfortunately I can’t do this any longer). It started in the early days of punk / new wave, and mainly for when I went out clubbing. Having said that, for about 3 years I used makeup every day. It was a glamorous period.
Once I’d got the confidence to do so, I graduated from a bit of eyeliner around the eyes to something more extravagant. I was inspired (as indeed were a lot of the punks & latterly goths) by Chinese Opera makeup, Japanese theatre, Egyptian art, and so on. Essentially makeup that you can see at a distance. I have a few of my own efforts in my Livejournal gallery, though unfortunately the photographic quality is not that good. Also the iconic photographs of Soo Catwoman & Jordan. They’re great iages.

http://pics.livejournal.com/davidbr1/gallery/000092yk
http://pics.livejournal.com/davidbr1/gallery/00007cgz
http://nihilismontheprowl0.tripod.com/seventies/id122.htm
http://www.flickr.com/photos/42843488@N06/3972862724/

There’s plenty of photographs of Chinese Opera to be fund. I’ve included links to a couple of sites, and also the actor Phillip Levine’s website. He used his own bald as a canvas.

http://www.flickr.com/photos/hsirius/tags/chineseopera/
http://www.pearlmagik.com/bayareacantoneseopera/aboutopera.htm
http://www.philsays.com/

Finally a couple of videos. I actually met Yoko in Camden Market in London many years ago. I can report that her makeup was every bit as immaculate as in this video. It’s admirable to achieve that on Sunday lunchtime.

https://www.youtube.com/watch?v=H9fbaI-vAd0
https://www.youtube.com/watch?v=P8fRThaVLsg

So in summary a bald head makes a good canvas, and it would seem a shame not to take advantage of that opportunity. I’d be very interested to hear about anyone else’s experiences of trying more experimental makeup.