Waylon Jennings: Celebrate the Outlaw Country Icon’s Birthday With His Best Songs

by Jim Casey
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Waylon Jennings was a talented individual. Yes, that’s an understatement. It’s easy to recognize Waylon’s talent if you’re a fan of country music. Just take a dive into his body of work. It’s amazing. But what truly made Waylon amazing was his individualism.

Waylon marched to the beat of his own drum. And country music was all the better for it.

In the 1970s, Waylon became the leader of the Outlaw movement. He wasn’t elected. He was destined. Because of his individualism, Waylon helped liberate country music from its Countrypolitan shackles. Of course, the Nashville Sound/Countrypolitan era produced plenty of great country music from the likes of Patsy Cline, Ray Price, Eddy Arnold, Glen Campbell, and more. I’m not bashing the sleek-sounding stylings of the era. But by the 1970s, Waylon was ready to do things his way. He was ready to put the nitty gritty back into country music.

Waylon wanted to use the musicians, producing, and studio of his choosing. He wanted to make his music, not what his label decreed. At the time, his demands were unheard of. But guess what? Where there’s a will, there’s a Waylon. The future Hall of Fame member got his way, and he started creating some of the genre’s best albums—ever: Lonesome, On’ry and Mean (1973), Honky Tonk Heroes (1973), The Ramblin’ Man (1974), Ol’ Waylon (1977), and more.

Waylon Jennings’ Greatest Hits

Waylon, 64, died on February 12, 2002. On what would have been his 84th birthday on June 15, 2021, let’s take a look at a few of his best tunes. And his 1979 Greatest Hits album is a great place to start.

In fact, Waylon’s Greatest Hits is his best-selling album of all time. The RIAA has certified the album as 5X Platinum for sales of 5 million units. The 11-song offering features No. 1 hits “I’m a Ramblin’ Man,” “Are You Sure Hank Done It This Way,” “Luckenbach, Texas (Back to the Basics of Love),” “Mamas Don’t Let Your Babies Grow Up to Be Cowboys,” “I’ve Always Been Crazy” and more.

Check out the chart-topping success of three tracks from the seminal album.

‘I’m a Ramblin Man’

Waylon released “I’m a Ramblin’ Man” as the lead single to his 1974 album, The Ramblin’ Man. Penned by Ray Pennington, “I’m a Ramblin’ Man” became Waylon’s second No. 1 single (after ‘This Time”) when it reached the top of the Billboard Hot Country Songs chart in September 1974.

‘Are You Sure Hank Done It This Way’

Waylon Jennings paid homage to one of his heroes, Hank Williams, with a nod to the honky-tonk days of yore. Basically, the song was a tongue-in-cheek middle finger to the Nashville Sound establishment that preferred “rhinestone suits” and “new shiny cars.” The tune hit No. 1 on the Billboard Hot Country Songs chart in November 1975.

‘I’ve Always Been Crazy”

“I’ve Always Been Crazy” is one of Waylon’s quintessential hits. Waylon penned the song about his individualism, and basically makes no apologies for who he is. Released as the lead single to his 1978 album of the same name, “I’ve Always Been Crazy” reached No. 1 on the Billboard Hot Country Songs chart in September 1978.

Outsider.com