It's sugar-coated shabbyness. I have been there in wintertime, all the rides and attractions were closed, but it´s still nice to have a walk on the beach or spot some funny looking storefronts and vintage-looking rollercosters. A perfect backdrop for photoshootings, a gem for friends of vintage typography. On 4th of july hot dog eating contests are held here (they actually do that!).
I have old friends in San Francisco who grudgingly tell me that the High Line is everything that's wrong with New York. Well, too bad. To me, it embodies a culture that's constantly reinventing itself: a defunct elevated railway that was becoming a burden to the city ("we used to climb up there to throw garbage bags full of rotting Korean food at the Hasids!", noted a successful photographer's assistant) becoming a startling example of urban greening for the public good. The expert landscaping makes it feel like walking on a Montauk beach - but a stone's throw from some of New York's most progressive galleries and hotels.
The best underground shows you will find will have free pbr and models as far as the eye can see. They are rarely announced, so keep your eyes out for promising openings, especially with Milk Underground coming up.