Near the end of his life, Jerry Garcia recorded a children’s album with David Grisman. You wouldn’t necessarily pick a depressive end-stage heroin addict to sing children’s music, but against all logic, the album is superb. The high point is their wry, jazzy arrangement of “Teddy Bears’ Picnic.”
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Sir Paul McCartney has a heavy presence in the lullaby rotation for the same reason that the writers of old jazz standards do: easily singable tunes, easily understandable lyrics, and big direct emotions. Okay, maybe you wouldn't want to sing "Helter Skelter" or "Why Don't We Do It In The Road" at bedtime, but most McCartney songs suit the mood perfectly.
Everyone knows the Mama Cass version, and hers is fine, but nothing can ever touch the Ella and Louis recording. The lyrics make it an obvious lullaby, but there's so much more happening here...