Vaughn Meader 'The First Family' (Won)

1963 Album of the Year

To be fair, a spoken-word comedy album won the Grammys' top prize just two years earlier, but at least that was the legendary album The Button-Down Mind of Bob Newhart (thoughalso giving Bob Newhart the best new artist award really muddied the Grammys' musical waters). But this comedy album was just a goofy take on the Kennedys by a long-forgotten impressionist. And it bested a pair of timeless classics: Ray Charles' Modern Sounds in Country and Western and Tony Bennett's I Left My Heart in San Francisco. (Needless to say, Meader's career as a Kennedy impersonator ended on Nov. 22 of that year.)