1. “Cryin’ Time” by Buck Owens

For some reason, I'm absolutely obsessed with this song. I literally listen to it and then rewind it and just keep rewinding it. I could listen to it on repeat for hours and still love it. I just can't pin what it is that makes me play it over and over and over and over and over again though. Is it the opening? Is it the way Buck Owens harmonizes? Could it be the instruments? Or is it the lyrics?

I'm going to go listen to it again to find out.

2. “City Lights” by Ray Price

What can I say? I’m a sucker for a nice fiddle opening. The fiddle is literally my favorite part of early country music that you just don’t here in any of the “country” songs produced to today. Plus the harmony on the chorus is absolutely killer.

3. “Walkin’ The Floor Over You”  by Ernest Tubb

Ernest Tubb is a classic. Is it really a list of greatest classic country hits if he isn't on it? No, no it's not. Plus, how can you not sing along to “Walkin’ The Floor Over You?"

4. ​“I’m So Lonesome I Could Cry” by Hank Williams

Elvis once said this was the saddest song he ever heard. And I mean, it's about crippling loneliness and pure sorrow. Besides, Hank Williams pretty much paved the way for modern country music (you know, before it all became garbage) and his songs are truely timeless.

5. “Tennessee Waltz” by Roy Acuff

If you want really old school, Roy Acuff’s the way to go. He was performing even before Hank Williams. As you can tell from “Tennessee Waltz,” Acuff’s music is very traditional. (Another favorite of mine is “The Wabash Cannonball” because some of the instruments actually sound like a train whistle).

6. “Precious Memories” by Jim Reeves

While not everyone can sing gospel songs well (sorry, Alan Jackson), nobody can ever beat Jim Reeves. His gospel songs are the greatest. There's just something about his rich, baritone voice that makes this the best version of “Precious Memories" to ever exist.

7. “Life Goes On (I Wonder Why)” by Charlie Walker

What can I say about “Life Goes On (I Wonder Why)” that will do it justice? Really, no words do this song justice. It’s just that great.

8. “I Fall To Pieces” by Patsy Cline

Patsy Cline is another timeless artist and “I Fall To Pieces" is always a classic. I mean, is it really a “Greatest Old Country Music Songs” list without “I Fall To Pieces?”

9. “Hang My Head And Cry” by Marty Robbins

Marty Robbins is perhaps most well known for his songs about cowboys dying somewhere in Texas. I mean, there's the whole “El Paso" trilogy and “San Angelo," just to name a few. But, his non-cowboy songs are just as good, and “Hang My Head and Cry" is one of them, with “Bouquet of Roses" and “Don't Worry" being a close second and third.

10. “It Wasn’t God Who Made Honky Tonk Angels” by Kitty Wells

Fun fact, Kitty Wells was the first solo female artist to have a No. 1 Billboard country hit with “It Wasn't God Who Made Honky Tonk Angels," the answer song to Hank Thompson's “Wild Side of Life." Even though she didn't write it, this song is super badass for the time period because it calls out men for their unfaithful ways in a time where that was uncommon, particularly for a female country artist. #Feminism

11. “She Needs Someone To Hold Her (When She Cries)” by Conway Twitty

Conway's voice is just absolute perfection. Period. It's probably a scientific fact that he had the most perfect voice known to man. Probably. In all seriousness, “She Needs Someone To Hold Her (When She Cries)" is pure perfection.

12. “After The Fire Is Gone” by Conway Twitty and Loretta Lynn

I'm not a huge Loretta Lynn fan, but even I have to admit that Conway and Loretta have the most perfect harmony ever. I’m not kidding. Conway’s smooth voice just blends so beautifully with Loretta’s. You could say that their harmony is literally music to your ears.

13. “My Shoes Keep Walking Back To You” by Ray Price

I cannot even begin to tell you how much I absolutely love this song. It is one of the greatest songs ever written, in my opinion. Like I said, I’m a sucker for that nice fiddle opening. And how can you not sing along with those lyrics? There are many excellent versions out there, but Ray Price probably has the best.

14. “You Win Again” by Hank Williams

Hank Williams was a true poet. He just knew how to effectively convey heartbreak and sorrow, and “You Win Again” is no expection. Even though it’s no “Your Cheatin’ Heart” or “Cold, Cold Heart,” it’s one of my absolute favorite songs that I just play on repeat for hours on end.

15. “Act Naturally” by Buck Owens

If I could make this list Buck Owens and Hank Williams, I would (they’re kind of my favorite artists, if you can’t tell). Seriously, it was super difficult limiting myself on their songs. “Act Naturally” is probably one of Buck Owens’s most well known songs, and for good reason too. Just listen for yourself and you’ll see why.

16. “Long Black Veil” by Lefty Frizzell

Ususally a song about capital punishment is super depressing, and this is, but it’s also a really great song. The lone guitar and Lefty drawing out the vowels just make it even more haunting. It just sends chills up your spine.