21. "The Little Drummer Boy," Harry Simeone Chorale20th Century Fox 121 b/w "Die Lorelei"
Highest chart position: #13 US & UK (1958)
Recorded October 1958, New York, NY
The Bing Crosby / David Bowie version of this classic, from a mid-Seventies Christmas special, remains the favorite these days, but the pop-culture joke (and the stagy post-hippie love vibes of the added song) wears more thin every year. This 1958 version, while not the original, is still the standard, having hit the Top 40 for five straight Christmases in a row (a record unequaled in modern chart history -- not even Bing could pull that off). It has something to do with the loveliness of the tune, taken from ancient Czech folksong, and the unique view of the Nativity, translated back in 1941. But Simeone's chorales were always known for their holiness, and since this is a holy song about a holy moment, it fits -- Harry even recorded this one in a Greenwich Village cathedral to give it the proper hushed respect.