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Tough choice. Best documentaries I've seen. Man on Wire was astounding. So was Dear Zachary, except it just made me want to jump off the highest building I could find. While I can't see myself rewatching Dear Zachary soon, or often, I cannot deny its unparalleled quality.
Dear Zachary all the way. Both are great but Dear Zachary will stick with me forever/
Both fantastic, but Dear Zachary went straight into my top 20. I cannot recall being so moved by a film in a long time. I'm a 20 year old male and I cried like a 2 year old. There are not many films that can invoke such an emotional response. Man on Wire was great, but Dear Zachary was extraordinary. To echo Matthew004, it will stay with me forever.