Even after his passing, Toby Keith continues to live on not just through his music, but through the kind of stories that perfectly captured who he was: fearless, funny, and never afraid to tell on himself.
One of the most legendary — and hilarious — tales from Toby Keith’s life involves a single night with none other than Willie Nelson, a man whose reputation as country music’s most famous cannabis connoisseur is unmatched.
Willie Nelson has smoked with just about everyone, including Snoop Dogg, who once famously admitted Willie “smoked him under the table.” While Willie has slowed down in recent years, his love for high-grade marijuana has always been legendary — and his generosity with it even more so.
Toby Keith, on the other hand, was never much of a smoker.
That’s what made this night unforgettable.
The story dates back to Las Vegas, where Toby was in town for Charles Barkley’s birthday celebration. Willie Nelson happened to be performing that night at the Hacienda, and Toby joined him onstage for a couple of songs. After the show, Willie casually invited him to hang out on the bus.
That’s when things went sideways.
According to Toby, Willie pulled out what he described as “real chronic, medicinal stuff.” Wanting to be polite — “When in Rome,” as he put it — Toby joined in. Despite only taking a few hits, the effect was immediate and overwhelming.
“I couldn’t even function,” Toby later recalled. “It was the most hardcore weed I’d ever had… unlike Bill Clinton, I did inhale.”
Within minutes, Toby knew he was done. His ears were burning, his head was pounding, his breathing felt off — and Willie was sitting there smiling, fully aware that he had absolutely leveled him.
“He knew he got me right,” Toby said.
Toby stood up, announced it was time to go, and Willie replied with perfect timing: “Good timing.”
A car took Toby straight back to his hotel room. He missed Charles Barkley’s entire birthday party — his first real night off in Las Vegas — and went straight to sleep. Willie Nelson had, quite literally, sent him to another planet.
That one night became country music folklore and eventually inspired Toby’s fan-favorite song Weed with Willie, co-written with Scotty Emerick. The track was recorded live and included as a bonus on Toby’s 2008 album Shock’n Y’all.
The song, much like the story, wasn’t about glorifying weed — it was about knowing your limits, laughing at yourself, and respecting a legend who plays in an entirely different league.
In the end, Toby Keith didn’t try to keep up with Willie Nelson.
He learned his lesson.
And country music got one of its most beloved stories — and songs — out of it.