We have a couple unusual bicyclists but the most unusual is the mostly naked bicyclist. Every day at 4:30 he's either out on Apalachee Pkwy. or LaFayette St. in Tallahassee, FL, hauling it on his bike with krate style handlebars. The bicycle seat is way up so it looks like he's standing. All he wears is a little Speedo. He'll never be hit by a car because he's highly visible. Actually, I'm surprised he hasn't caused auto accidents from people looking. Check out an image at the bottom of Joe's Bicycle Shop home page http://www.joesbikeshop.net/ - scroll way down.
There is also a sometimes homeless artist who rides a tandem hand-painted vintage bike. The bicycle basket is made of macrame with wood limbs that are bent for support. The wheels are decorated with yarn to look like a dream catcher. The bike looks almost organic. I really like it.
I don't know if this cyclist is homless or not, but I see him riding, mostly downtown, on a bike covered with magazine pictures - Playboy and the like, and his spokes are filled with 'spoke cards' of the same.
I doubt this approach gets him much, but I could be wrong.
I'll try to get some images of Viper Von and his organic tandem bike this Saturday. He usually hangs out at Art in the Park. He had his art taken by the local police for not having an art license and doing some stylized nudes, along the style of Salvadore Dali. In FL you have to have a $50 license to sell art, even if you're a visiting artist or sell art out of your bicycle basket or alongside the road. I brought him some art supplies and bought a couple of pieces he had in his basket. Will post a link to images soon.