Phil Everly, who with his older sibling Don set the standard for harmony singing in rock ‘n’ roll in the Everly Brothers, died Friday in Burbank of complications from chronic obstructive pulmonary disease. He was 74.

“We are absolutely heartbroken,” his wife Patti told the LA Times, saying the disease was due to the late musician’s lifetime of cigarette smoking. “He fought long and hard.”

Everly, who was inducted into the Rock and Roll Hall of Fame with his brother in 1986 and the Country Music Hall of Fame in 2001, mastered the art of close harmony singing in his family’s country group as a child. With his brother, he recorded a string of unforgettable ballads and rockers for the Cadence and Warner Bros. labels in the late 1950s and early ‘60s. The list includes such enduring hits as “Bye Bye Love,” “All I Have to Do Is Dream,” “When Will I Be Loved” (written by Phil Everly) and “Cathy’s Clown.”

The Everly Brothers’ pioneering blend of country and rock ‘n’ roll spread their influence on artists ranging from Bob Dylan to the Beatles, Beach Boys, Simon and Garfunkel and beyond. In November, singer Norah Jones and Billie Joe Armstrong of Green Day released “Foreverly,” a duets album featuring all Everly Brothers songs.

In later years, Phil and Don Everly had a famously rocky relationship. Following an acrimonious split in the early 1970s, the Everlys regrouped in 1983 for renewed recording and touring.

Phil Everly was born Jan. 19, 1939, in Chicago, to country performers Ike and Margaret Everly. With his brother, two years his senior, he began performing with the family act at the age of 10 on the family’s radio show on KVA in Shenandoah, Iowa. As youngsters, the Everly boys excelled at the close-harmony style of such country precursors as the Blue Sky Boys, the Monroe Brothers, the Delmore Brothers, and their contemporaries the Louvin Brothers.