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Who Is Harry Nilsson (And Why Is Everybody Talkin' About Him)? is a good one. I'd heard of the guy before but didn't know much about him. It was incredible how many songs I recognized during the film for only vaguely being aware of the guy. Here's a wiki description:

David Leaf and John Scheinfeld interviewed close to three dozen of Nilsson's friends, colleagues and extended family, who all shared their memories of Harry Nilsson, his music and how it affected them. This was put together in a documentary where we follow Harry Nilsson from childhood to death, enjoying the highs and lows along with him, from Grammy wins through divorce and substance abuse.

The film features original interviews with well-known friends and acquaintances of Nilsson, including Perry Botkin, Jr., Micky Dolenz, Terry Gilliam, Mark Hudson, Eric Idle, Al Kooper, Randy Newman, Yoko Ono, Van Dyke Parks, Richard Perry, Jimmy Webb, Paul Williams, Robin Williams, Brian Wilson and The Smothers Brothers. Also included are interviews with Nilsson's family, including his wives and children. Perhaps the most notable absence in the film is Ringo Starr, who does not feel comfortable talking about three people in person: John Lennon, George Harrison and Harry Nilsson. Another notable absence in the film is arranger-composer George Tipton, who worked closely with Nilsson on nearly all of his early RCA recordings - they reportedly had an unexplained and permanent falling-out, and Tipton refused to be interviewed for the film.