Remembering Country Legend Waylon Jennings with Four of His Biggest Hits

On this day (February 13) in 2002, the country music world lost a legend when Waylon Jennings died. He passed away in his Chandler, Arizona home after a long battle with diabetes at the age of 64. His tragic passing came just months after he was finally inducted into the Country Music Hall of Fame in October 2001.

Videos by American Songwriter

Jennings was many things. He was a songwriter, a singer, a musician, a trailblazer, and an inspiration. From the early days of his career when he played bass with Buddy Holly’s band to his breakout career as a country crooner to taking his place at the forefront of the Outlaw Country movement in the ‘70s, Jennings proved time and time again that he was a singular talent.

[RELATED: 4 Songs for Anyone Who Wants to Dive into the Deep Discography of Waylon Jennings]

Today, we’re remembering the country legend with four of his biggest solo hits.

1. “This Time” from This Time (1974)

Waylon Jennings released his first single “Jole Blon” in 1959 with some help from Buddy Holly. Six years later, he released his major label debut album Folk-Country in 1965. While he was consistent in his release schedule, it would be nearly another decade before he landed his first single at the top of the Billboard Hot Country Songs chart.

Jennings wrote “This Time” and released it as the lead single from his album of the same name. It was the first of 16 singles to reach the top of the chart.

2. “Luckenbach, Texas (Back to the Basics of Love)” from Ol’ Waylon (1977)

Let’s go to Luckenbach, Texas with Waylon, Willie, and the boys. Nearly every country fan knows that legendary line and the rest of this No. 1 hit by heart. More than four decades after its release, “Luckenbach, Texas” is still a favorite among Waylon Jennings fans. At the time of its release, it topped the Hot Country Songs chart and landed at No. 25 on the all-genre Hot 100, giving him his first crossover hit.

Bobby Emmons and Chips Moman penned the song which references Jennings, Nelson, Jerry Jeff Walker, Hank Williams, and other country legends as well as a few timeless songs. However, Hoss wasn’t a fan. “I knew it was a hit song, even though I didn’t like it—and still don’t,” he wrote in his 1996 autobiography.

3. “Amanda” from Greatest Hits (1979)

Bob McDill penned “Amanda” and Waylon Jennings recorded it for his 1974 album The Ramblin’ Man. However, he wouldn’t release it as a single until five years later on his first greatest hits collection. It went to No. 1 on the country chart and stayed there for three weeks.

“Amanda” is a bittersweet love song about a man who believes his wife could have done better without him. However, he sings it with such a powerful combination of love and sorrow as to make it believable.

4. “Rose in Paradise” from Hangin’ Tough (1987)

Penned by Jim McBride and Stewart Harris, “Rose in Paradise” was Waylon Jennings’ final No. 1 single. He released in 1987 as the lead single from Hangin’ Tough.

“Rose in Paradise” tells the story of a rich banker from Georgia who falls in love with a beautiful woman named Rose. A jealous and possessive man, he kept his young wife locked away in a large estate he called “Paradise.”

The song sees the banker hiring a gardener to keep an eye on the grounds and Rose while he is away on business trips. She mysteriously disappears and, near the song’s end, the banker dies thinking about her.

Featured Image by Tom Hill/Getty Images