David Browne has a nice piece on the Dead in The Daily Beast. David is certainly right that much of the Dead's coolness had to do with their authenticity and integrity. As I say in No Simple Highway, they gave mainstream culture a wide berth and showed that hippies could flourish on their own preferred terms.
In many ways, the Dead defined or embodied cool here in the Bay Area when I was growing up, especially until 1975 or so. Another source of their cool, I would say, was their studied nonchalance--or sprezzatura, as the Renaissance Italians called it. Then and now, Californians like to make difficult things look effortless. (If you need to put another face on that, try Joe DiMaggio.)
When I moved to NYC in my twenties, I learned that studied nonchalance didn't have the same cachet there. Quite the opposite: The whole point was to be serious, dramatize your effort, and win the Most Industrious award. Those who didn't were considered lightweight, flakey, etc.
If you're not attuned to the aesthetic of effortlessness, or if you aren't familiar with how hard it is to perform a difficult task at a certain level, you might be tempted to take things at face value and diminish the achievement. I think that's still happening with the Dead, in part because they consistently downplayed their effort. But you don't last three decades in the music business unless you're committed to your project. In short, my advice is to enjoy the sprezzatura, but don't let it fool you.
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