LOS ANGELES (AP) ― There is no more beautiful sound than the voices of siblings swirled together in high harmony, and when Phil and Don Everly combined their voices with songs about yearning, angst and loss, it changed the world.

Phil Everly, the youngest of the Everly Brothers who took the high notes, died Friday from chronic obstructive pulmonary disease. He was 74.

He left a towering legacy that still inspires half a century after The Everly Brothers’ first hit.

You could argue that while Elvis Presley was the king of rock ’n’ roll, Phil and Don Everly were its troubled princes. They sang dark songs hidden behind deceptively pleasing harmonies and were perfect interpreters of the twitchy hearts of millions of baby boomer teens coming of age in the 1950s and ’60s looking to express themselves beyond the simple platitudes of the pop music of the day.

The Everlys dealt in the entire emotional spectrum with an authenticity that appealed to proto rockers like the Beatles and Bob Dylan, who gladly pass the credit for the sea changes they made in rock to the ruggedly handsome brothers. The Beatles, the quartet whose pitch-perfect harmonies set the pop music world aflame, once referred to themselves as “the English Everly Brothers.” And Dylan, pop culture’s poet laureate, once said, “We owe these guys everything. They started it all.

Their hit records included the then-titillating “Wake Up Little Susie” and the era-identifying “Bye Bye Love,” each featuring their twined voices with Felice and Boudleaux Bryant’s lyrics that mirrored the fatalism of country music and the rocking backbeat of modern pop music. These sounds and ideas would be warped by their devotees into a new kind of music that would ricochet around the world.

In all, the brothers’ career spanned five decades, although they performed separately from 1973 to 1983. In their heyday between 1957 and 1962, they had 19 top 40 hits.

The two broke up amid quarrelling in 1973 after 16 years of hits, then reunited in 1983, “sealing it with a hug,” Phil Everly said.

Don Everly said in a statement to The Associated Press on Saturday morning that though they quarreled, the brothers still loved each other.

Although their number of hit records declined in the late 1980s, they made successful concert tours in the U.S. and Europe.

They were inducted into the Rock and Roll Hall of Fame in 1986, the same year they had a hit pop-country record, “Born Yesterday.” They also are members of the Country Music Hall of Fame, a nod to their heritage. Phil Everly was born to folk and country music singers Ike and Margaret Everly on Jan. 19, 1939, in Chicago, two years after his older brother.