What Was The Last Single Buddy Holly Released Before He Died?

February 3, 1959, is still one of the most tragic days in popular music history, so tragic that it has since become known as the "Day the Music Died." That morning, rock 'n' roll icons Buddy Holly, Ritchie Valens, and J.P. "The Big Bopper' Richardson were all killed when the small plane they were riding on crashed in an Iowa cornfield. All three, especially the 22-year-old Holly and the 17-year-old Valens, were in the prime of their careers, and one can only wonder what they could have achieved had they not gotten on that plane for an upcoming show in Minnesota.

Compared to Valens and The Big Bopper, Holly arguably had the most interesting career at that time, as he had just recently split from his backing band, the Crickets, due to issues with management. That meant he was just getting started as a solo act, and to echo the earlier point, it's interesting to theorize how things could have turned out for Holly in the long run after he parted ways with the Crickets. He was, however, actively recording music shortly before the Day the Music Died, and had, in fact, released what would turn out to be his final single slightly less than a month before his untimely passing.

The last single Buddy Holly released before his death came out on January 5, 1959. The single featured "It Doesn't Matter Anymore" on the A-side and "Raining in My Heart" on the B-side, and both happened to be part of the last studio recording session Holly ever participated in. The session, which took place on October 21, 1958, marked his first and only time to record with a string section, and it also produced two other songs — "Moondreams" and "True Love Ways."

While the title "It Doesn't Matter Anymore" has an eerily prophetic ring to it, the lyrics, which were written by a then-17-year-old Paul Anka, are standard fare for the time in terms of subject matter. It's a simple, yet catchy and fast-paced breakup song where the protagonist tells his ex that all the good times they spent together no longer matter, and that when he'll be dating someone else, the ex herself won't matter anymore. Anka, however, acknowledged the "tragic irony" of the song's title after Holly's death, promising that he would donate his composer's royalty to the late musician's widow, Maria Elena Santiago (via Songfacts).

Both "It Doesn't Matter Anymore" and "Raining in My Heart" — the latter also a breakup song, albeit with a slower tempo — charted posthumously for Holly, with the former song reaching No. 13 on the Billboard Hot 100 on March 30, 1959, and the latter peaking at No. 88 one week later.