John Wesley Ryles might not be a name that many modern country music fans know, but he certainly had his time at the top of the industry.

His career got off to a start in the 1960s when he was still a teenager and he ran off a string of hits through the 1980s.

Sadly, that one-time teen star has died. He was 74.

His death was first announced on social media by Tracy Pitcox, owner of Hart of Texas Records.

“At age 17, he made his debut in 1968 with the single “Kay,” a Top Ten hit on the Billboard Hot Country Singles charts, and the title track to his debut album for Columbia Records,” Pitcox wrote. “Ryles later recorded one album, Reconsider Me, for the Plantation label, which produced a No. 39 single in its title track. It was followed by two non-album singles, ‘Tell It Like It Is’ and ‘When a Man Loves a Woman,’ both on the Music Mill label in 1976.

“He then moved to Dot records,” the post continued. “His first single on ABC/Dot, ‘Fool,’ made it to No. 18 on the Hot Country chart followed by his highest-peaking single, the No. 5 ‘Once in a Lifetime Thing.’ When that label merged with MCA Records, he issued the album Let the Night Begin there. The first single, ‘Liberated Woman’ climbed to No. 14 on the Billboard Hot Country chart. It was followed by a rendition of ‘Always on My Mind,’ which went to #20 on the Billboard Hot Country chart. The last song released from this album, ‘Perfect Strangers,’ reached No. 24 on the Billboard Chart.”

Pitcox wrote that since the release of his last single in 1988, Ryles has worked as a background vocalist and in the production side of the industry.

Country singer Mark Willis also posted about Ryles’ death.

“We lost a GIANT in the music industry,” he wrote. “John Wesley Ryles sang more harmonies on records, that to the listener, sounded like the artist themselves! He could blend with ANYBODY! John sang on my first four records and always had a flawless blend with the lead vocal. It was perfect. My condolences to Joni and his entire family! Please lift them up in prayer.”

Parade Magazine noted that Ryles became “one of Nashville’s most in-demand background vocalists,” after 1988. The outlet reported that he worked with the likes of Alan Jackson, Brooks & Dunn, Randy Travis and Blake Shelton.

He was married to Joni Lee, the daughter of country music icon Conway Twitty.