9. Ben Bostrom Wood Helmet

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Ben Bostrom has had many cool helmets during his career, but when I first saw this one I was puzzled. What … is … that? Turns out B-Boz drew inspiration from, of all things, hardwood floors, and wanted to decorate his helmet in a similar manner. Hence the “wood” helmet was born. I really shouldn’t be surprised at its, um, uniqueness considering Benjamin’s free-spirited nature, but the wood helmet strikes a chord with me in a way I really can’t explain. It just makes me laugh. Considering that was the second criteria for making this list, I had to include it. It’s too bad this graphic never made it into production, because I’d wear it every chance I got.