"Jingle Bell Rock," Bobby Helms (Decca)

Although many songs mentioned on this site predate it, this 1957 song is probably the first one to cross rock 'n roll with Christmas in an overt way. Ironically, considering this site's reluctance to promote country music, Helms actually was a country singer with a number of Billboard chart hits before this song, and its wild holiday success at the time aligned him with rock 'n roll for all time in the public eye. This isn't as widely covered as a lot of contemporary holiday songs, but it's hardly neglected. Bobby Rydell and Chubby Checker did their own version in 1961, and the Hall and Oates cover was pretty big in its day; it was a 7-inch or 12-inch single between 1983 and 1985 and turns up on compilations from time to time. By the way, Helms' original B-side was "Captain Santa Claus (And His Reindeer Space Patrol)." Helms had several other hits in the 1956-7 time frame, and continued to record through the 1980s. His original "Jingle Bell Rock" even charted at no. 18 in the US adult contemporary charts upon re-release in 1996, a year before his death.