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What are the three saddest jazz songs recorded between 1939-1969?

We’re limiting the years to 1939-1969, a period that is widely considered the "Golden Age of Jazz."

Tip: Identify one, two or three songs, and enter the song and the name of the artist and, if possible, the recording as follows: "Blue in Green" by Miles Davis, from Kind of Blue. Also, list more “mainstream” pieces that other jazz fans would likely recognize.

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