Chart Rewind: In 1974, Waylon Jennings Hit No. 1 for the First ‘Time’

On June 22, 1974, Waylon Jennings’ “This Time” became his first No. 1 on Billboard’s Hot Country Songs chart. It was released as the lead single from his same-named LP, which he produced with Willie Nelson.

With “This Time,” which Jennings solely wrote, he achieved his first of 16 Hot Country Songs leaders (with his 31st entry on the chart). He notched his first of 53 top 10s with “(That’s What You Get) For Lovin’ Me,” which reached No. 9 in 1966. Among his No. 1 total, “Highwayman” – by Jennings, Nelson, Johnny Cash and Kris Kristofferson – led in 1985.

Jennings was born June 15, 1937, in Littlefield, Texas. His storied career comprised an on-air stint at KLLL Lubbock, Texas, and his famed run as the balladeer on CBS’ The Dukes of Hazzard in 1979-85.

In 1959, Jennings played bass in Buddy Holly’s band on his Winter Dance Party Tour. He performed with Holly during the latter’s final show at the Surf Ballroom in Clear Lake, Iowa. Holly, J.P. Richardson (The Big Bopper) and Ritchie Valens all perished in a plane crash that Feb. 3 following the concert.

Jennings, who played a big part in country music’s Outlaw movement of the 1970s, was inducted into the Country Music Hall of Fame in 2001. He died in February 2002 at age 64 at his home in Mesa, Ariz., after a long battle with diabetes.

Jennings’ legacy is in vogue in 2024. His rebel ways were one of the most talked about elements in the recently released Netflix documentary The Greatest Night in Pop, which chronicles his walking out of the recording of USA for Africa’s megahit, and four-week 1985 Billboard Hot 100 No. 1, “We Are the World.”

“Waylon in ’75,” a track on Chayce Beckham’s debut album, Bad for Me, is just one example of today’s artists paying homage to him, Meanwhile, Shooter Jennings, the 45-year-old son of Jennings and Jessi Colter (who married in 1969), has announced that he’s uncovered unreleased music from his father and plans on releasing it in 2025.