Harry Nilsson's affection for Randy Newman's songwriting runs deep, and Nilsson Sings Newman captures something rarely heard: one eccentric genius interpreting another's catalog with genuine reverence. Recorded during a period when Nilsson's distinctive voice—nasal, tender, capable of sudden emotional depth—could bend Newman's baroque pop and character-driven narratives into unexpected shapes. These aren't covers so much as conversations between two songwriters who understood America's underbelly and its small-town loneliness in ways most pop music ignored. Newman's gift for irony and sentiment finds new resonance through Nilsson's interpretive lens, transforming songs like "Caroline" and "Dayton, Ohio 1903" into intimate character studies. This reissue restores a fascinating document from a catalog that continues rewarding close listening—proof that beneath Nilsson's whimsical surface lived a serious musician with exquisite taste.