Oh boy you are gonna love Andy Anderson. Check out his Powell video. He is incredibly creative in his skating and you will never see him without his helmet.

Howevee as a skater myself I would rather wear a helmet on my bicycle than on my skateboard. I skate mostly flat and do things that I can more or less control. I didn't git my head in 12+ years of akating once and I am not planning to start now.

If I would try crazier things, skate bowls or vert ramps I'd definitely reconsider : )