Outlaw country emerged in the 1970s when artists like Willie Nelson, Jessi Colter, Kris Kristofferson, and Waylon Jennings united in their efforts to resist a Nashville studio system that frequently controlled what songs country artists recorded and how they were produced. “For us, ‘outlaw’ meant standing up for your rights, your own way of doing things,” Jennings once explained.
But just as the Outlaws defied the strictures of Nashville’s mainstream, this group often made headlines for defying the legal system — running from the cops, getting thrown in prison, breaking out again, pulling guns in bar brawls and smoking copious amounts of weed. The illicit activity and the alluring air of danger often resurfaced in the Outlaw’s songs, enthralling generations of listeners.
With the upcoming Cinemax animated series, Mike Judge Presents: Tales From the Tour Bus (debuting September 22), taking a look at some of the wildest stories in country history, here’s a look at some of the wildest outlaws in country music.
Paycheck was famously truculent from a young age — during a stint in the Navy, he was thrown in jail for attacking an officer who outranked him, and later broke out of prison twice — and he took his name from a heavyweight boxer. He paired this pugilistic sensibility with a knack for songwriting and an idiosyncratic, slippery voice, so when Outlaw country rose to prominence in the 1970s, allowing brawling singers with layabout tendencies to become musical heroes, Paycheck was primed to capitalize. The same year Wanted! The Outlaws came out, Paycheck released “11 Months And 29 Days,” a bluesy number that celebrated his inner desperado: “Busted in Austin, walkin’ around in a daze,” Paycheck sings, not sounding the least bit sorry. “I’m sittin’ in a slammer, lookin’ out through these bars in a haze.” The next year, he doubled down with the No. 1 hit “Take This Job And Shove It” and “Me And The IRS,” some of the fiercest declarations of independence you’ll find in country music.