Harry's first big hit was "Everybody's Talkin'". Although he originally recorded the Fred Neil song for his Aerial Ballet album, the song became a hit when it was used in the film Midnight Cowboy.

Harry's all-time biggest hit was his cover of the Badfinger song "Without You" from Harry's Nilsson Schmilsson album. Nilsson Schmilsson also spawned the hits "Coconut" and "Jump Into the Fire".

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