Waylon Jennings Kicked Off an 8-Week No. 1 Streak With an Album That Told His Own Outlaw Story in Every Track. WN

On this day (November 11) in 1978, Waylon Jennings reached No. 1 on the Billboard Top Country Albums chart with I’ve Always Been Crazy. The album spent the final eight weeks of the year at the top spot. Like many of his 1970s LPs, it contained multiple memorable tracks, including one written about the time Jennings almost faced serious jail time.

Waylon Jennings Hated This Song But It Became One of His Biggest Hits

Jennings found early success after the release of his 1965 major label debut, Folk Country. Throughout the rest of the decade, he consistently sent singles to the top 20 of the country chart. The 1970s saw him climbing to new heights. Songs like “Good Hearted Woman,” “The Taker,” and “Pretend I Never Happened” were top 10 hits. Then, in 1974, he found his first No. 1 with the title track from This Time.

His popularity continued to grow as the Outlaw Country movement, in which he was a major player, gained traction. Jennings, Willie Nelson, and a handful of other artists enjoyed high praise from listeners and critics alike. However, the “Outlaw” label came with consequences. By the time he recorded I’ve Always Been Crazy, Jennings was seemingly growing tired of the label. He made his feelings clear in the No. 5 single, “Don’t You Think This Outlaw Bit’s Done Got Out of Hand.”

Hear Waylon Jennings' Unreleased Demo 'Good Time'

Waylon Jennings Turns a Drug Bust Into a Hit Song

While Waylon Jennings was recording I’ve Always Been Crazy, federal agents busted into RCA Studio, ready to arrest the country star. They’d received a tip that a large package of Peruvian marching powder had arrived at the studio for Jennings. Fortunately for him, Richie Albright was able to think on his feet. He was able to grab the package, sneak it to the bathroom, and flush the evidence.

Jennings pretty much tells the story in the song’s lyrics. This is something that has been talked and written about countless times. However, many focus on the story of the near-miss bust and all but ignore the heart of the song, even though it’s right there in the title.

Waylon Jennings Discography: Vinyl, CDs, & More | Discogs

In his autobiography, Waylon Jennings said that Outlaw Country was never about criminality. Instead, so-called Outlaw artists disregarded the trends of the day and made the music they wanted to make. This is evident when you put the bulk of Jennings’ Honky Tonk Heroes up against other popular albums from 1973 or Willie Nelson’s Red Headed Stranger against popular albums from 1975. Jennings’ rock-infused honky tonk sound and Nelson’s jazz-leaning, stripped-down arrangements stand out like a sore thumb. That’s what made them Outlaws, not the lives they lived behind the scenes.

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