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Cap did dish up the live acts- coming very close to a juvenile ( Johnny Carson) My guess from the period you stated would be either Joan Baez ( was it a Confederate Army cap?) or maybe Rita Coolidge ( no relation to Calvin) It sounds like the woman may have had health problems that prompted the short hair and headgear. I am only guessing.

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Q: I saw a woman with short hair and a cap playing guitar on Captain Kangaroo in mid or late 1960s but don't know her name I only saw her once Who was she?
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