How well do you know outlaw country songs?

Willie, Johnny, Waylon, and Merle.


By the early 1970s, the Nashville recording industry held country music in its sway. Both commercially and creatively, Nashville was the center of the country music world. But for a small group of iconoclastic artists, true freedom lay in waiting elsewhere. 

Nobody's quite sure when "outlaw country" officially started. Was it when Waylon Jennings opted not to re-sign with RCA Records? Or did it maybe have more to do with Willie Nelson's Nashville home burning down, prompting him to move back to Austin?

Whether you're a genre historian or a neophyte, we hope this quiz can illuminate a small corner of the music world for a moment. Be sure to share your thoughts, feelings, and score in the comment section below. Oh, and tell us your favorite Willie tune while you're at it, partner. 

  1. “I sat with my pen in my hand, trying to think up the worst reason a person could have for killing another person, and that’s what came to mind.” What song was Johnny Cash speaking about?
  2. "And there's nothin' short of dyin'; Half as lonesome as the sound; On the sleepin' city sidewalk; Sunday mornin' __________"
  3. Who wrote the song "Pancho & Lefty?"
  4. Waylon Jennings' signature hit: "Are You Sure ____ Done It This Way?"
  5. Which singer began her classic 1975 album "Pieces of the Sky" with a cover of Rodney Crowell's "Bluebird Wine?"
  6. Merle Haggard: "“I Think I’ll Just Stay Here and _____”"
  7. What was the name of the supergroup that featured Johnny Cash, Willie Nelson, Waylon Jennings and Kris Kristofferson?
  8. Who sang the lyrics “Hey pretty baby, are you ready for me? / It’s your good rockin’ daddy down from Tennessee"?
  9. According to a 2012 hit, Willie Nelson wishes for which of the following post-mortem?
  10. What is the name of contemporary country singer Jason Isbell's backing band?

How well do you know outlaw country songs?

Your Result...

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Antenna2 7 months ago
6 - Contemporary Country (Anne Murray, etc.) was my thing, not Honky-Tonk, and while I enjoy Johnny Cash, some of his songs were dark prison blues - that's a rough place for a mind to be more than 30 seconds....
AprilDee 7 months ago
7 out of 10 my parents would have kicked me square in my a*s. "If you pay attention to your school work like you do your music you would be a straight A student" a quote from my late parents. I just lost my saint of a momma on May 30, 2023. I am a brain injury survivor who is trying my best to move on like my momma ask me to many years ago. See she told my little sister and myself that when it's my time girls I don't want you two to cry I want you girls to remember the good times and move on.
Mark 8 months ago
10 out of 10...knew all but the last one, and I guessed on that...I know my Cash, Willie, Waylon, et al, but who the hell knows (or cares) about Jason Isbell?
JeffPaul76 8 months ago
"You got 3 out of 10" ----"Might be time to pick up those headphones and give these tunes another listen!" ----I only knew #s 1 and 2, & guessed on correctly #4. The rest of the tunes I never heard of, or listened to.
KawiVulc 8 months ago
8/10... definitely wasn't getting #10 except by guess, haven't paid country much attention since all 3 of my preset stations were playing Taylor Swift at the same time 8 or 9 years ago.
IndianaRockz 8 months ago
9/10. #10 about a Jason Isbell (whoever he is) was a total guess after ruling out the band The Pretenders. I picked Emmylou cuz she had that song rockin' song "Two More Bottles of Wine" but I have no idea if it was from the referenced album. I LUV me some Merle, Waylon, & Willie!!! I grow'd up on that good stuff (along with other genres) so classic country has a very special place in my heart. 🎶🍻📻🎸🎻🎹🎤🛻
LabLove 8 months ago
9 of 10. Cut my teeth on this stuff in the 60's.
MrsPhilHarris LabLove 8 months ago
Love your avatar.
Bapa1 8 months ago
7/10. Big fan of Waylon and Willie. Also Cash. Have two Highwaymen CDs. Sometimes during pledge month PBS shows The Highwaymen concert. Really good.
MikefromJersey 8 months ago
"You got 7 out of 10. Well if you ain't perfect, you're pretty darn close!"

NJ used to have quite a vibrant country music scene back in the 60's and 70's.
Freddy the German Cowboy had a joint in Hillside that could get pretty wild.
The large German immigrant community in the area loved country music,
a residue of a keen long time interest in Germany in Western books
and movies since the 1800's. They even made Westerns in Germany,
some with the Englishman Stewart Granger.
Mark MikefromJersey 8 months ago
I hardly think of New Jersey as a hotbed for country, but two major country stars were born there...Eddie Rabbitt (born in East Orange) and Clint Black (born in Longbranch, but raised in Texas).
Moverfan Mark 7 months ago
You forgot Richard Sterban of The Oak Ridge Boys--he's from Camden!
Wendy57 8 months ago
I much prefer the old country songs to the new ones.
Who is Jason Isbell anyways ? 🤷‍♀️
bj1606 8 months ago
10 for 10 most of all these were on the jukebox in my moms bar yep the Deep South about maybe 300 ft to the Gulf of Mexico the Red Neck Rivera. When it was fun to be alive and young . Seen Waylon Sunday at Al and Glenn’s before Eloise
MrsPhilHarris 8 months ago
5/10 I think I knew one of them.
KJsunshine 8 months ago
7 of 10, answered way too quick on #1 and got it wrong, Missed #3 and I never heard of Isbell and of course I got it wrong.
I should have done a lot better. Oh well.
Moverfan KJsunshine 7 months ago
I got nine out of ten (sorry, Jason, never heard of you). And the only reason I got the first one right is because I know Shel Silverstein wrote A Boy Named Sue and Ring Of Fire has nothing to do with killing. Although killing a parent because you don't like what they named you is a pretty damn stupid reason for it, too...
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