Standing shoulder-to-shoulder with jazz, country music is one of the few purely American musical art form. Just as the mighty San Joaquin is feed by the Tuolumne, Merced and Stanislaus rivers, country music is enriched by the tributaries of Gospel, Blues and American Folk. Both are made better for the inputs. Often described as the music of the poor, the illiterate and the dumb, I can’t be the only who thinks calling the songwriting ability of Hank Williams, Sr. ignorant is near the same as calling William Faulkner a hack, right? Are you feeling shades of Tom Petty’s “Southern Accents” ‘cause I sure am.

Before we dive too deep into this, drop me a comment below with your favorite country music track and tell me a little bit about it. If you’re not a fan of the genre, tell me why.
“Country music is full of songs about little old log cabins that people have never lived in; the old country church that people have never attended,” the historian Bill C. Malone says in Ken Burns’ documentary Country Music. “But it spoke for a lot of people who were being forgotten, or felt they were being forgotten.”
Since its beginnings in the early 1920s, country music has been about both sides of the coin, the head and the tail. I’m can’t imagine it was his goal, but legendary OKeh Records producer Ralph Peer set this dichotomy in motion in 1927 when over a 24-hour period in a Bristol, Tennessee studio he recorded both Jimmy Rodgers, whose sound was the soundtrack of a Saturday night bender, and the Carter Family, whose hymns were the call that beckoned you to church service on Sunday. The sin and the redemption served up on a platter. Country music has always been a blend of nostalgia and newness, sentiment and sales, redemption and sin. But here’s the thing, country music is both U.S. and us, whether we chose to embrace it or not. Country is songs with stories for everyone, life’s little vignettes played out in 3½ minutes.
Country music played an important role in my life and the life of my family. Dad was a huge fan of both old school country and, what was at the time new, the Outlaw Country movement featuring such musical luminaries as Willie Nelson, Waylon Jennings and others. While it didn’t make this mixtape, I can’t help but think of John Denver’s classic “Country Roads Take Me Home,” as an integral part of both my personal history and the story of my family. Mom was a singer growing up who often sang while she drove, all five of us of kids sat in the back just drifting off listening to Momma’s voice up front as she navigated the dark, snowy, Alaska roads. One of her favorites to sing was that John Denver track.

When my brother, Patrick, (@ChasingVinyl on TikTok) asked me to collaborate on a classic country mixtape, I jumped at the opportunity. Probably the biggest thing we had to hash out was who got to pick which song given our shared history. We did it though, a mix of songs from our past that for different reasons spoke to each of us while each track touching a piece of our family history drenched in classic country. What did we leave out? What’s track do you consider essential in a classic country playlist?
Side A - @ChasingVinyl
Poncho and Lefty – Willie and Merle: My love of classic country music starts with my father. This song reminds me of driving across the US as a young child as we moved from base to base. When we moved to Alaska, my parents made a massive drive starting in New Jersey, going to Texas, Kansas, California, and finally Washington state before shipping the Jeep Wagoneer to Alaska. On this trip, my dad had a CB radio installed. His handle was The Red-Headed Stranger.
Convoy – CW McCall: Another traveling classic for my dad and, frankly, a family favorite. All of us kids would sing this song when it came on.
Teddy Bear – Red Sovine: My dad made the playlists, and my mom did the driving. However, Dad always made sure to include songs my mother would like. This is one of those.
Give Me 40 Acres – The Willis Brothers: Another family favorite that was guaranteed to keep the kids entertained for a few minutes.
Jolene – Dolly Parton: As far as I am concerned, you can’t make a list like this without including Dolly. Another of my mom’s favorites, and dad always included songs for her.
Coward of the County – Kenny Rodgers: This one is all for me. I have always loved this song and suspect I always will.
Give My Love to Rose – Johnny Cash: I came to this song much later in life. I know my parents liked Johnny Cash, but I don’t remember them playing this one.
Me and Paul – Willie Nelson: When it comes to Willie Nelson, On the Road Again seems like the right choice. I think this song does a better job of conveying life on the road.
Tennessee Whiskey – Chris Stapleton: So, clearly not classic country. Despite this, the feel of this song fits so well.
The Race is On – George Jones: This was another family favorite and another one guaranteed to occupy the kids for a bit.
Is Anybody Going to San Antone – Charley Pride: This one fits so well, as we traveled to San Antonio multiple times to visit my grandparents.
Tulsa Time – Don Williams: Rounding it out is Tulsa Time. This is a salute to my brother-in-law, who jokingly yelled at a band to play this song for, according to my sister, the whole night. They never played it.
Side B - @TriggerHippie74
One Dyin’ And A Buryin’ – Roger Miller: A fox introduced me to Roger Miller, specifically Disney’s Robin Hood. As a youngin’ I couldn’t reconcile the two tracks but as I grew up the depth in simplicity of this song has always stuck with me.
Rockin’ Chair Money – Hank Williams, Sr: Coming home from my tour in Iraq this was one of the first songs that helped bring me back. I didn’t fight in every battle from here to the V-J day but Hank’s words helped me realize it was okay to sit down in my rocking chair and just take a break, I’d earned it.
Time of the Preacher – Willie Nelson: The Redheaded Stranger was one of the first records I bought when I started collecting vinyl as an adult – a direct result of my father’s love of this album. To this day I can still listen beginning to end and sing every note of this country masterpiece. Time of the Preacher introduces us to the story, brings us in and lets us know this isn’t going to be your typical story.
I’ve Always Been Crazy – Waylon Jennings: I would consider this one of my personal anthems with the title saying everything you need to know. Outlaw country played heavily in my families’ rotation and Waylon was one of Dad’s favorites.
Flowers on the Wall - The Statler Brothers: Most likely due to it’s inclusion in Quentin Tarantino’s Pulp Fiction soundtrack, but I love this song due to its subversive happiness. It totally throws “This is fine” vibes and I love it so.
Sing Me Back Home – Merle Haggard; While Dad was a big fan of Merle and he was often played in our house, this one sticks with me due to some pickin’ and grinnin’ sessions in the hot dessert sands of Iraq. I was assigned to the 39th Brigade Combat Team from Arkansas and about half-way through our deployment a regular cast of characters, including the Brigade Deputy Commander, would break out their guitars around our hooch and sing to anyone who would listen … boy oh boy did that group love them some Merle Haggard.
He’ll Have to Go – Jim Reeves: Soothing baritone voice, beautiful orchestrations, heart breaking lyrics, this song absolutely crushed my romantic heart as a little one and can still pull a tear or two from eyes with a bourbon or two in me.
The Chair – George Strait: See above about hopeless romantic. My wife always accuses me of being a cheesy romantic and growing up listening to lines like “Baby, do you think there’s a chance, that maybe later on I could drive you home, No I don’t mind at all. Oh, I like you too and to tell you the truth … that wasn’t my chair after all.” How did I have any chance? There’s a reason Tyler Sheridan’s character in “Yellowstone” remarks to Jimmy – “There’s three gods in Texas: the Almighty, Buster Welch and George Strait.”
Dixieland Delight – Alabama: During the mid-80’s Alabama was a thing, they were turning out hit after hit and every damn one of their songs was just fun. If Dad didn’t have a mixtape in the car radio, we sure as hell were listening to KIAK country on the A.M. radio dial and hoping this song would come on.
Old Hippie – The Bellamy Brothers: This one spans generations. I wouldn’t say it was in heavy rotation when we were growing up, but Dad owned it and occasionally he would play this record. Where it came into its own for me was one random day my oldest son, Kerouac, sent it to me on our Discord chat channel – “Think this one sums you up, Dad!” Been a favorite ever since.
Grandpa (Tell Me ’Bout the Good old Days) – The Judds: The very first time I heard this song I loved it, the harmony of mother and daughter, the steel guitar, the simple message. I saved up my one-dollar-a-week allowance and as soon as I could, got Mom and Dad to take me to Fred Meyer to buy the 45. Absolutely drenched in nostalgia, it’s probably easy to dismiss this one as saccharine and while I don’t take every word to heart, things like giving your word and meaning it and sticking around even when things get hard still resonate deeply with me.
To Beat the Devil – Kris Kristofferson: I knew I had to pair this one with John Prine’s Sam Stone. I mentioned earlier I’m a combat vet, some of my dearest friends made it home but didn’t make it soon after and a few Beat the Devil.
Stand By Your Man – Tammy Wynette: Country music gets an accurate knock for being overly white and overly male (there’s some growth in that area in the newer generation but not nearly enough) so it was important to me to include some of the strongest women voices in the genre. Patrick included Dolly so I thought it important to include Tammy and Loretta with their signature songs in this mix.
Sam Stone – John Prine: Deeply personal. There are days where I think John Prine must have known my Uncle Ron and modeled the character of Sam Stone after him. A Marine Crops Vietnam Vet, Ron was my personal hero growing up. Just as I feel like my brother compliments me, my Uncle Ron perfectly complimented my father and between these two men, I learned everything I needed to be a man in this world. Ron lost his battle with PTSD even as he tried his best to self-medicate and I miss him every day.
Coal Miner’s Daughter – Loretta Lynn: Champion of the common man, Loretta Lynn has been singing the songs of the everyday struggle for as long as her lungs could take air. While I chose this track to end this mix on a familiar note, perhaps “The Pill” would have been more appropriate. There was a time when country music was a protest genre filled with outlaws, activists, and misfits – Loretta was one of those wonderfully beautiful people.




The beginning was a fantastic mix of trucking classics that made me remember riding in the backseat as a kid too. I had never heard it before, but "Give Me 40 Acres" was entertaining! "Flowers on the Wall" brought back a ton of memories of camping up along the Pacific coastline forests of Oregon and Washington, but my grandma always preferred the Eric Heatherly cover (I think it was the sideburns) and I think I lean toward that version too. Any time I hear Alabama that's all I end up listening to for the next week, so RIP to my Discover Weekly algorithm.
I'm more familiar with country prime or whatever they call '80/90s country now, so I wasn't sure how much I would enjoy this, but I really got into this mixtape. Can't wait for the next one!