From everything I've heard from friends in New York, Supreme is not the shop it was in the 90's. Apparently they make a ton more money from the streetwear kids, and focus more on streetwear than they do on the actual skate side of the skateshop these days, which, if true, is really really lame.
I'll still watch the video though.
And I took cherry to be like as in when a car or something else valuable or collectible is in great condition it is said to be "in cherry condition," so there you go.