Its practicers are attracted to the long, phallic shape. They think they are more manly than anyone else who rolls, because of the board's penile shape and the riding style: standing stoicly like a man, without squatting, thrusting, or contorting of any sort.
No tricks of any sort, strictly manly stances. The one kinda cool thing they can do is slalom down a hill to scrub off speed, similar to a snowboarder. They will still jump off the moment things get dicey.
In reality these guys are passed by grandmas on 3-speed bicycles, even downhill.
Longboarding looks kinda cool...oh wait, that old lady just passed him on her grandma's bike.