I agree and disagree with your post.
I doubt anything will evolve of this "thug" image in skiing anymore than it has now. I guarantee that the majority see it as ridiculous. That being said, more props to him if he wants to push it against a majority perception.
I think you get it right in the second half of your statement, "he just likes to have fun man, the movie was fun, even if a little laughable at points, it was fun." That is where skiing's image is, not in being "thug", "emo", "newschool" or "old school". So if I see a kid on my hill with a pant leg rolled up and a bandana coming from every which way, that's fine, as long as he's enjoying himself. Not my image, but who am I to say it's not his.
I listen to a lot of punk music, but I have listened to a alot more hip hop now because of ski movies. Talib Kweli and Mos Def being two of my favorites.
cheers.
Dan