Top 10 Outlaw Country Songs

It’s cool to be an “outlaw” again, at least in country music. And no, we’re not talking about those who flaunt the law or do jail time just to get the firsthand experience. Instead, the “outlaws” in this case are artists who are taking more control over their own music and occasionally drifting away from country’s conventions—for example, Eric Church, Kacey Musgraves and Gary Allan, to name a few.  

Their heroes were (and still are) Merle Haggard along with Waylon Jennings, Willie Nelson and the other architects of the so-called Outlaw movement in country music, which goes back about 40 years. Merle, Willie, Waylon and friends wore their hair long, shunned the rhinestone-studded suits and adopted a lifestyle more closely associated with rock stars. In the musical arena, they openly defied the pop-oriented Nashville Sound and were also highly critical of the entire Nashville record system, where artists were often told what songs they could sing and who would produce them. They stood up for their own music and assumed greater control of their material.

Below is a list of some of our favorite country songs that we feel are part of the ongoing “outlaw” story.  

1. “Whiskey River,” Willie Nelson

Video features a performance by Willie in 1974.

Buy on iTunes and Amazon.

2. “High Cost of Living,” Jamey Johnson

Buy on iTunes and Amazon.

3. “How ’Bout You,” Eric Church

Buy on iTunes and Amazon.

4. “Family Tradition,” Hank Williams Jr.

The performance featured in the video has Hank Jr. performing with Kid Rock on CMT.

Buy on iTunes and Amazon.

5. “Long Haired Country Boy,” Charlie Daniels

This video features Charlie performing the tune in the ’70s on TV.

Buy on iTunes and Amazon.

6. “I’m the Only Hell My Mama Ever Raised,” Johnny Paycheck

This video features a performance by Johnny at the Chillicothe Correctional Institute in 1993 with none other than Merle Haggard introducing him to the stage.

Buy on iTunes and Amazon.

7. “Mama Tried,” Merle Haggard

This is an Austin City Limits performance from Oct. 1985.

Buy on iTunes and Amazon.

8. “Cocaine Blues,” Johnny Cash

Buy on iTunes and Amazon.

9. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” Waylon Jennings & Willie Nelson

A performance from a 1986 Farm Aid event in Austin, Texas.

Buy on iTunes and Amazon.

10. “Ain’t Living Long Like This,” Waylon Jennings

A very cool performance from 1988 with Waylon sharing the stage with the man who composed the song, Rodney Crowell!

Buy on iTunes and Amazon.

Listen to the whole playlist on YouTube!

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