It was fifty years ago today, on October 21st, 1958, that Buddy Holly went into the studio for the last time, cutting "True Love Ways," "It Doesn't Matter Anymore," and "Raining in My Heart." (There may have been other tracks laid down at that session; my Buddy Holly discography is not exhaustive.) According to a guy I heard on the radio this morning, this was also the first time that a rock & roll song was recorded with an orchestra.
Holly was in New York at the time, rather than his regular digs in Clovis New, Mexico, and his producer wasn't Norman Petty but Dick Jacobs, who also directed the orchestra on the session.
I hear a lot about how Leiber and Stoller were the first to use strings on an R&B song with the Drifters' "There Goes My Baby," in 1959. I can't find when that song was recorded, but the single came out in May of 1959. Since "It Doesn't Matter Anymore" had made the Top Forty by March of 1959, eventually peaking at Number Thirteen, I think we can assume that it was the first string-laden rock single.