On This Day in 1979, Waylon Jennings Topped the Charts With an Album Featuring an Autobiographical Classic and a Tribute to His Friend Buddy Holly

On this day (November 13) in 1979, Waylon Jennings was on an eight-week run at No. 1 on the country albums chart with I’ve Always Been Crazy. It was one of his most successful albums. Some of the LP’s tracks allowed listeners a glimpse of what was going on behind the scenes. Additionally, It contained a six-minute medley of Buddy Holly hits.

Jennings released I’ve Always Been Crazy in July 1978. It reached No. 1 on the Hot Country Albums chart on November 11 and stayed there for the rest of the year. Kenny Rogers’ Kenny knocked it out of the top spot in the first week of 1980.

[RELATED: On This Day in 1980, Waylon Jennings Was at No. 1 With Every Outlaw’s Favorite TV Theme]

Major hit albums were nothing new for Jennings. He had been on a hot streak since 1974, when This Time reached No. 4 in 1974. The next year, Dreaming My Dreams became the first of four consecutive chart-topping LPs. While he was happy for the success, he was disappointed to see outlaw country becoming the very thing it was created to defy–the sound of Nashville’s mainstream. The storm brewing behind the scenes fueled his addiction issues.

Jennings was famously arrested by the DEA in 1977 after they tracked a package containing a large quantity of blow that had been shipped from his manager’s New York office to the studio in Nashville where he was working. His drummer, Richie Albright, flushed the product before authorities found it, saving Jennings some serious jail time. He wrote “Don’t You Think This Outlaw Bit’s Done Got Out of Hand” about the situation.

The album’s title track also hinted at the substance abuse issues he was dealing with behind the scenes.

Waylon Jennings Covers Buddy Holly

Waylon Jennings is widely remembered as a country music legend and one of the originators of outlaw country. However, before he came to Nashville, he was an aspiring musician in Texas. Eventually, his pursuit of fame took him to Arizona, where he met Buddy Holly. The two became friends and Holly hired Jennings to play bass in his road band.

A year later, in 1959, he accompanied Holly on the ill-fated Winter Dance Party tour. Jennings was supposed to be on the plane that crashed and killed Holly, the Big Bopper, and Ritchie Valens.

Twenty years later, while working on I’ve Always Been Crazy, Jennings paid homage to his late friend. The album features a track called “Medley of Buddy Holly Hits,” which features snippets of “Well All Right,” “It’s So Easy,” “Maybe Baby,” and “Peggy Sue.”

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