Who was Jack Sheldon and why does he matter? Part of the answer can be found in Trying to Get Good: the Jazz Odyssey of Jack Sheldon, a documentary released in 2008. Produced by Doug McIntyre and Penny Peyser, the film is part biography, part confessional and part intervention as Sheldon and his music colleagues shed light on the West Coast jazz scene in the 1950s and Sheldon's playing gifts and puckish personality. Jimi Mentis sent along links to the documentary below.
My only quibble is that the film missed critical moments to follow up on. For example, early on we learn that Sheldon's father abandoned Sheldon's mother and that she spent years looking for him. That thread is dropped instantly. Wow, I have at least five followup questions on that alone, since the abandonment surely had everything to do with Sheldon's personality and life.
But more to the point, the documentary is a loving tribute, and it's a joy to see so many talented artists talk about one of West Coast jazz's trumpet greats. To purchase the documentary, go here.