Frank Sinatra photographed by Bill Gottlieb, 1947, at a recording session

When I was an adolescent, I was obsessed with being cool and hip. An older friend once got quite upset with me when he asked me what I wanted to be when I ‘grew up’ and I replied, “I just want to be cool.”

I love the way Wynton Marsalis defines ‘cool’, in the documentary Bill Gottlieb: Riffs

“I always have loved this picture of Frank Sinatra. Just the whole thing, is like the essence of cool. He’s looking off; kind of got a harshness.

“The essence of cool is always harsh, because cool is always the denial of something. So the warmth of cool is very deep. The actual essence of hipness is denial; and that’s what makes you hip – is that you’re able to push things away from you.”

Bill Gottlieb was a jazz aficionado, critic, and photographer. He was one of the first and best photographers to properly document jazz musicians in the ‘golden age’ of modern jazz.

Using a big Speed Graphic press camera which had a very limited film capacity – two negatives per cartridge, which needed to be separately loaded – his rapport with the musicians and his sense of the perfect moment were crucial to these most iconic of jazz photos.

Many of his photos were taken in the short span of two years, 1946-1947.  Bill Gottlieb: Riffs is a documentary about his photographs and the musicians, with many colorful and telling anecdotes. If you like biographies, photography and/or jazz, you will love this documentary.

Another great photographer of note was Francis Wolff. He co-founded Blue Note Records with Alfred Lion. It was one of the preeminent jazz labels, known for supporting new artists and new ideas in jazz. They were taste-makers and visionaries, always on the cutting edge. Another good documentary that tells their story is: Blue Note – A Story of Modern Jazz.