I don't think Dylan songs work well with skate footage. Not that it couldn't possibly work, but it just never has, as far as I am concerned. Maybe "Obviously 5 Believers" could work, for someone maybe. I don't know. It just seems that people who might use his music may really like Bob Dylan, but that doesn't mean you should skate to his music in some video.
If anyone could, probably Nate Jones could make it work.