I'm glad this was brought up. Years ago, I wasn't into rails at all, and preferred to watch videos that weren't urban focused. I loved hitting the jumps, hips, etc but rails/boxes didn't interest me one bit. One season we had a post season rail-jam for charity, and I figured I'd go and mess around on the little boxes and tables, it was for a good cause. That day I managed to go from 50-50's, to some sort of inbetween crooked, to boardslides. 6 years or so later I kinda got it into my head that I should ride EVERYTHING and once I learned to "lock on" to a rail or box everything changed. I don't come from much of a skateboard background, so it was all pretty new to me. I've only done urban riding a couple times and it was on mellow stuff, benches mostly but chilling with a few friends and focusing my riding on one object really helped on those days.
Honestly at 31 years old I'm still learning rail stuff, but doing a couple nose-slides during a park run is plain fun once it becomes easy. I don't dress "gangsta" and I never will, at 31 years old my goal isn't to draw attention anymore I just want to ride everything and have fun doing it. Half these people seem to put as much time into fashion as they do their riding. Right now I'm anxiously looking forward to another pre-season rail event in mid October, they bring in shaved ice from skating rinks and usually set up a rail, box and table. 2 dollar brews, good times.
With that said, I am not into the big acid drop stuff or straight airing off a high ledge into a parking lot. Not into watching it in a video either. That's just guts, not progression in my opinion.