Jackie Lomax, the British singer/songwriter who frequently collaborated with Paul McCartney and George Harrison in the early days of Apple Records, died on September 15th while on vacation. According to The New York Times, Lomax passed away following a battle with cancer.

A Liverpool native, Lomax was part of the same scene that produced the Beatles in the early 1960s; as a young man, he often performed at the legendary Cavern Club with his band The Undertakers. In 1967, Lomax and his band at the time (called The Lomax Alliance) were taken under the wing of Beatles manager Brian Epstein, who got them a recording contract with CBS. After Epstein’s death, Lomax moved to Apple where he began work on his solo debut, Is This What You Want? Lomax’s first single for the label, “Sour Milk Sea,” was written by Harrison and featured a backing band of Harrison, McCartney, Ringo Starr, and Eric Clapton; despite the considerable backing behind Lomax, the song was a commercial non-starter, largely because the Beatles released “Hey Jude” that same week.

After leaving Apple Records, Lomax relocated to America and continued recording, working with the likes of Levon Helm. His last album, Against All Odds, is set to come out in January on Angel Air Records.

Lomax is survived by his wife Dionne Armitage; his daughters Vicki, Louise, and Janine; his five grandchildren; and his stepson Terry Richardson, now a famous photographer.