"...does anyone know of other interesting works where someone playing all the 
parts has a dialogue with "themselves," so to speak?

Did Peter "Stoney" Emshwiller ever finish "Later That Same Life" in which the 
filmmaker interviews himself 38+ years in the future?
https://time.com/4104698/man-interviews-self-38-years-later/ 

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Subject: FrameWorks Digest, Vol 121, Issue 27

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