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What won the Grammy for Album of the Year in 1960? It was the most successful album from the act, spending two and a half years on the Billboard charts and netting them their first of three Album of the Year awards.
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| "Come Dance with Me!" - Frank Sinatra |
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| "September of My Years" - Frank Sinatra |
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| "A Sailor's Guide to Earth" - Sturgill Simpson |
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| "Bridge over Troubled Water" - Simon & Garfunkel |