I do it quite often, to stretch my back, warm a cold hand, open my lungs up a bit and just for fun. I haven't always been able to, but I taught myself about ten years ago, and was surprised at how easy it was. I had to tuck my tailbone well in and sit really upright, to "get" it. Now I enjoy feeling how I can move around, look over my shoulder, remove my pack and jacket and put my pack back on (on a good day), and in general steer my bike well no hands. I will usually put a hand on the bars if I see someone approaching, mostly to be polite so that they won't worry that I'm about to ride into them.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett