Ol’ Waylon Playlist: Celebrate Waylon Jennings’ 85th Birthday With His ‘Dam’ Fine Catalog

by Jim Casey

For a lot of country music fans, Waylon Jennings is the GOAT. And understandably so. He’s the damn “dam builder” (“Highwayman,” anyone?). Waylon needs no defense. If he’s your Greatest of All Time, enough said. Waylon was a grade-A badass. The country music icon became known as much for his rugged individuality as his music. And his music endures, more than 20 years after death. Waylon was only 64 when he died of complications from diabetes on Feb. 13, 2002.

On what would have been his 85th birthday on June 15, 2022, let’s revisit a little bit of the Ol’ Waylon magic and his damn dam building.

Ol’ Waylon

After finding success on the charts in the 1960s with song like “The Chokin’ Kind” (No. 8), “Only Daddy That’ll Walk the Line” (No. 2), and more, Waylon Jennings became stymied by the creative control of the producer-polished Nashville Sound era. So, he broke free, spearheading the Outlaw movement of the 1970s along with like-minded Willie Nelson. Waylon started making music the way he wanted to—with the band, studio, and producer of his choosing. It was unheard of at the time.

Waylon’s maverick recording style produced numerous Gold and Platinum albums, including 1976’s Are You Ready for the Country (Gold), 1977’s Ol’ Waylon (Platinum), and 1979’s Greatest Hits (5X Platinum). He hit the top of the charts more than a dozen times with songs like 1975’s “Are You Sure Hank Done It This Way,” 1977’s “Luckenback, Texas (Back to the Basics of Love),” 1979’s “Amanda,” and more.

In addition, he shared the top spot several times with his Outlaw cohort Willie Nelson, including 1975’s “Good Hearted Woman,” 1978’s “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” and 1982’s “Just to Satisfy You.” And who could forget his 1985 super union—The Highwaymen—with Willie, Kris Kristofferson, and Johnny Cash.

The Dam Builder

The Highwaymen’s first live performance took place at Willie Nelson’s annual 4th of July Picnic in 1985, where the four fellows gathered to sing three songs in Austin, Texas. Months before in December 1984, the foursome convened at Cash’s request, as Johnny was recording his new album, Rainbow. But instead, Johnny put his solo album on hold, and the four legends recorded 10 songs, including their new supergroup’s namesake and title track, “Highwayman.” The four-part narrative about a soul’s reincarnation was written by Jimmy Webb and previously recorded in 1978 by Glen Campbell. But Glen never released it as a single.

When the album dropped in May 1985, the single, “Highwayman,” rose to No. 1 as the foursome alternated verses: highwayman (Willie), sailor (Kris), dam builder (Waylon), and starship pilot (Johnny). In addition, the album reached No. 1 on Billboard’s Top Country Albums chart. Tours followed, as did two additional albums, 1990’s Highwayman 2 and 1995’s The Road Goes On Forever. While their subsequent albums never found the same success as their original endeavor, no country supergroup—before or since—has been able to unite a group of artists as singularly acclaimed as Johnny, Kris, Willie, and Waylon.

Here’s to the damn dam builder, Ol’ Waylon, on his 85th birthday.