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Stephen's entire interview with Harry Belafonte, rich with some good hearty humor. Especially when Stephen shyly asks if Belafonte still sings, to which he responds in a voice that has noticeably worn a little bit: "Occasionally..." Beat. Everyone smiles as Stephen starts singing one of Belafonte's signatures "Jamaican Farewell", to which Belafonte begins to sing along. Hearts immediately melted.
Similarly to the above, his interview with Julie Andrews ends with the two of them singing "Accentuate the Positive". After she'd turned him down several times throughout the interview when he asked her if she wanted to sing together.
His interview with Maurice Sendack, which happened a few months before he died. One part was shown after he died. Sendack was talking about one of his books, Higglety Pigglety Pop. Sendack and Colbert were cracking very few jokes during this part, and Sendack stated his philosophy on not trying to turn children away from the fact that the world is very harsh.
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