The Harry Simeone Chorale is best known for their iconic recording of "The Little Drummer Boy," which became a Christmas classic. Harry Simeone, the group's conductor and arranger, first recorded this song with the chorale in 1958. The popularity of this rendition helped establish the Harry Simeone Chorale as a notable name in Christmas music.

The group continued to record Christmas music, with albums like "The Wonderful Songs of Christmas" further cementing their place in holiday music traditions. Their style typically featured rich choral arrangements of traditional and contemporary Christmas songs.