Waylon Jennings’ Near Arrest: The Wild Story Behind “Don’t You Think This Outlaw Bit’s Done Got Out of Hand”
Waylon Jennings was one of country music’s greatest storytellers, but perhaps some of his best tales weren’t in his songs—they were his real-life experiences. His music was raw, honest, and filled with the kind of outlaw spirit that wasn’t just an act. One of the most legendary stories about Waylon isn’t just about his music—it’s about how he outsmarted the DEA and walked away without a charge, even when it looked like they had him cornered.
Waylon’s Drug Use & The DEA Sting
Waylon was no stranger to drugs, and by the late ’70s, his cocaine habit had spiraled to the point where he was reportedly spending $1,500 a day on it. It was no secret, and his son, Terry Jennings, shared even more details in his book Waylon: Tales of My Outlaw Dad.
In 1977, the DEA got wind of a package being sent to Waylon—a gift containing an ounce of cocaine. A suspicious employee at the private delivery service opened the package, saw the contents, and alerted the authorities. Instead of seizing it all, the DEA left a small amount and sent it on to its destination, hoping to catch Waylon red-handed.
The package was delivered to a recording studio in Nashville, where Waylon was working at the time. According to Terry, his father casually opened it, saw what was inside, and went back to work like nothing had happened. But moments later, DEA agents stormed in.
The DEA vs. Waylon Jennings: The Studio Standoff
As the agents entered, they first ran into Waylon’s drummer, Richie Albright, who quickly hit the call button so Waylon could hear everything going on outside. From inside the recording booth, Waylon could see what was happening, but the agents couldn’t see him.
Without hesitation, he tossed the package away, where it slid behind a baseboard at the bottom of the wall. Then, like a true professional, he continued recording as if nothing was happening.
When the DEA confronted him, they had a search warrant—but there was a problem. The warrant listed Waylon as the owner of the recording studio. In reality, he only rented it. His actual office was next door.
That technicality meant they had to leave and get a new warrant. And in the time it took for them to do that, Richie Albright had already flushed the cocaine down the toilet.
According to Terry, when the agents returned, one was furious because he realized they no longer had any physical evidence. One agent asked Waylon directly where the cocaine was, to which he coolly replied:
“If it ever was here, it ain’t here no more.”
The Aftermath & A New Outlaw Anthem
Even without evidence, the DEA still arrested Waylon on August 23, 1977, charging him with conspiracy and possession with intent to distribute. Before being taken in, he called his wife, Jessi Colter, and told her to get rid of anything that could be used against him.
Ultimately, though, Waylon walked free. His high-powered New York lawyers got all charges dropped, as the botched warrant made the case against him weak. Behind the scenes, prosecutors admitted they had nothing to hold him on.
The experience left such a mark on Waylon that he turned it into a song—”Don’t You Think This Outlaw Bit’s Done Got Out of Hand.” Released in 1978, the song became one of his defining outlaw anthems. It wasn’t just a song—it was a reflection of a man who had blurred the lines between his outlaw persona and his real life.
It would take another six years before Waylon finally quit drugs for good. But when he did, he stayed sober for the rest of his life, proving once again that the only person who could truly define Waylon Jennings—was Waylon himself.
