The Best Country Songs of All Time

This wasn’t an easy list to create.

The best country songs of all time can man different things to different country music fans. I certainly have what I think are the fifty best country songs of all time, but I know they’ll be different than the fifty country songs you think are best. And that list will be different from another country fan.

This was my best shot at trying to put together the best country songs. I tried to think about the best artists over the last 60 or so years in country music and include their best songs. I included authentic country songs, which are the ones I tend to enjoy more, but there are a few pop-country songs on the list as well.

This is one man’s list and I hope you enjoy and even make a playlist.

The Best Country Songs

50. Amazed – Lonestar

Back in the summer of ’99 you couldn’t turn on any radio station without hearing Amazed by Lonestar. I went to see the band at the local fair near my hometown and they actually played the track twice during their show. The fans were all chanting for the song again during the encore and the band proudly came out and did the song for a second time. It’s a simple love song really, but it was one of those instances where guys and gals just connected with the story.

49. Amy’s Back In Austin – Little Texas

Little Texas is band that took the band movement in hair metal in the ’80s and brought that vibe to country music. They racked up quite a few hits including this one at the tail end of their career. I always though Amy’s Back in Austin was a great country track. The music is country. The vocals are country and the story is country. The story is about a girl named Amy that heads back to Austin to her country life. It’s a breakup song about a girl that left for her life back home and the guy still misses her. It’s a song that can easily be forgotten, but I thought it was worth a spot on the list.

48. Sweet Southern Comfort – Buddy Jewell

Buddy Jewell only had a couple hits on the country charts but his talent seemed to warrant many more. One of his songs got me thinking it was worth a place on the list here. Sweet Southern Comfort is an ode to life in the South. The times are always good. The company is the best and the sweet sounds and tastes make the southern US something special. The people down there are unique and they are proud of where they live and what their life is all about. It’s a great song and one of the best of all time.

47. Workin’ Man’s Ph.D – Aaron Tippin

Aaron Tippin took this track to the top ten on the country charts in 1993. The song is hardcore country with an attitude. A tip of the hat to the working men and women out there Workin’ Man’s Ph.D is a rocking song about how hard work pays off when you live the country life. Aaron Tippin had numerous hits during the traditional time in country music in the ’90s and he even had success in the ’00s. I think this was his best country song and worthy of a spot on the list.

46. Brand New Man – Brooks & Dunn

In 1991, one of the greatest careers in country history was started with one of the best country songs of all time. Brooks & Dunn blasted onto the scene with Brand New Man and it rocked the country world. The song was a declaration of a changed man, but the song was also a declaration of a change in country music. Brooks & Dunn brought a little more rock and roll to country music and ruled the ’90s and ’00s. They were the biggest duo in the world for many years and it all started with the great opening vocals from this great country track.

45. It’s A Great Day To Be Alive – Travis Tritt

Travis Tritt had a huge run of success throughout the ’90s in country music. He racked up hit after hit. He had fast songs and ballads and seemed to be on a roll that couldn’t be stopped. Things slowed down for a year or two late in the decade though, but Travis didn’t stay out of touch for long. In late 2000 Travis released the optimistic song It’s a Great Day To Be Alive. It climbed all the way to #2 on the charts and made its mark on the country world. We got Fu Manchu references and even a little tip of the hat to rice made in the microwave. Life isn’t so bad after all.

44. Nothin’ Better To Do – LeAnn Rimes

LeAnn Rimes has had an interesting career. Things got off to a fast, fast start for the teenager when she first hit the scene back in the ’90s. LeAnn drifted in and out of country music for a few years and she grew up and tried a few different things. Finally she discovered her own writing abilities and in 2007 she released what I think is her best song Nothin’ Better To Do. The song is uptempo and rips through the story of a woman struggling through temptation and evil. Keep those hands busy folks. Idle hands lead to nothing but trouble.

43. Two Sparrows In A Hurricane – Tanya Tucker

Struggling through everything life can throw at you seems to be a common theme in country music. The artists and the fans are not immune to the hurricanes life can throw at you during life. Tanya Tucker isn’t shy about sharing her own history of making poor decisions and rolling with all that life can throw at her. I don’t remember when this song first came out, but I do remember hearing it on the radio over and over over the last 15 years or so. It’s a great track about persevering with someone you love. It’s always a bit easier when you’re working toward your dreams with the person you love most.

42. I May Hate Myself In The Morning – Lee Ann Womack

In late 2004 Lee Ann Womack released this song. It was a bit of a comeback song for the authentic country singer. It brought her back to the authentic sound she loves so much. The song reached the top ten and won awards for being a great country song and one of the best of the year. Lee Ann’s sound is pure country and when she wants to she puts all her passion and experience into her songs. This one about giving in to temptation for just a night despite knowing you’ll probably regret it in the morning. I’ve always thought country music songs are great at acknowledging faults and this song fits that theory perfectly.

41. Every Once in a While – Blackhawk

I remember hearing Blackhawk songs on the radio all the time in the ’90s. These guys had a sound like nobody else during their run and really I haven’t heard anything like them since. They had the pure country harmonies and the expert musicianship. One of their biggest hits was Every Once in a While. It was a huge hit and remains popular on radio today. I crank it up and sing along every time it comes on in the truck. The chorus has a great melody and the story of two people struggling to get over each other make for a winning formula. It’s simply one of the best country songs of all time.

40. The Bluest Eyes In Texas – Restless Heart

In the late ’80s Restless Heart brought their easy listening country sound to country music and ruled the charts. With hit after hit the guys sold tons of records and packed tons of shows. Songs like The Bluest Eyes in Texas are still fan favorites even today. You’ll hear these guys on radio almost every day when you listen to country radio and especially classic country radio. They were a powerhouse of harmonies and their songs were just great country songs all around. A great band with one of the best country songs of all time.

39. Some Gave All – Billy Ray Cyrus

Billy Ray Cyrus isn’t really considered much of a country singer in lots of circles, but I remember when he had his run in the early ’90s. He had the hit everybody remember, but once you get past that song there is some really great music in Billy Ray’s history. Some Gave All is one of the songs people remember most about BRC and for good reason. It’s a song about dedication, passion, and hard work where others aren’t willing to sacrifice everything they have. The song fits a lot of situations in life and for that reason deserved a spot on the list.

38. Better Life – Keith Urban

Keith Urban is a country pop star from Australia. He was an unlikely superstar in country music, but his talent and passion made him the biggest star for numerous fans. In the ’00s Keith ruled the country award and rocked fans each night during his award winning performances and tours. The electric guitar slinger had his best country song with Better Life in 2005. It’s a song of hope, love, and succeeding in life with nothing but hard work and a little bit of hope.

37. The Gambler – Kenny Rogers

Kenny Rogers was the biggest superstar country music had ever seen in the late ’70s and early ’80s. He was selling ridiculous amounts of records during his heyday. With a blend of country and pop, Kenny took the country sound to new audiences all over the world. The Gambler has to be the song that defines Kenny’s career. The lead in to the chorus is something everybody knows and every card player knows for sure. It’s a great country song that defined an era in country music. It has to be included on this list.

36. Song of the South – Alabama

Alabama knew how to blend melodies into authentic country sounding stories. The guys ruled the charts in the ’80s and really changed the way bands were perceived in country music. Alabama was a pioneering group in country music and their songs had an impact on a generation of country fans. It was hard picking what is considered their best country song for this list, but I had to go with Song of the South. The song is about where the guys are from along with having that catchy chanting chorus that the band did so well. Every country fan can sing along with this track and they all get a hankering for some sweet potato pie after they sing it.

35. Two Dozen Roses – Shenandoah

Shenandoah had a run of hits in the late ’80s and early ’90s. One of their songs that still gets played a ton on radio is Two Dozen Roses. The song is about a guy that wishes he would have done the right things like get his woman two dozen roses. If he had done all of the right things perhaps he wouldn’t have lost her. Shenandoah broke up later in the ’00s, but still tour in some form without the lead singer that was part of the group’s most successful lineup. In any form it’s great to have them out still singing great songs like this best country song.

34. Ol’ Red – Blake Shelton

It wasn’t his highest charting hit, but Ol’ Red kind of defined Blake Shelton’s career in a way. The oddball story of a prison inmate tricking his way out of the clink became somewhat of a cult classic for the now male artist of the year. Blake had to work hard to convince his label to front the money for a video and Blake was able to turn the video into a great enhancement to a great song. Ol’ Red barely cracked the top 15 on the charts, but I bet it’s one of Blake’s most played songs. It’s a unique song with plenty of fans out there that know and love it.

33. Wild One – Faith Hill

Faith Hill seemed to be destined for country success. With her first single in 1993 she got off to a huge start. Wild One captured the hearts of every young girl at heart and made Faith a huge country star. The song is even one of those songs the guys love singing along with when they’re in the car alone. The song is catchy, optimistic, and free spirited. There is everything you love about a great country song here and with Faith Hill delivering there is plenty of passion and emotion in the story. Simply a great country song about a driven girl doing it her own way.

32. Brokenheartsville – Joe Nichols

Joe Nichols is one of the authentic country guys still finding a place in modern country music. We’re in a bit of a pop-country phase and while that’s Ok, I still like hearing the traditional sound on radio. Joe Nichols has turned in a steady career for about a decade now and his second big hit remains one of my favorites. Brokenheartsville is a classic sounding song about a brokenhearted guy finding comfort in his own sorrow. These are the kind of songs that have defined country music over the years and it certainly belongs on the list of the best country songs of all time.

31. Gunpowder & Lead – Miranda Lambert

Miranda Lambert has been one of my favorite country artists since I first saw her on the first season of Nashville Star. Her talent for performing and songwriting was evident from that show and she fulfilled her potential to the fullest. Over the last few years Miranda has racked up hit after hit, platinum album after platinum album, award after award, and huge hit after huge hit. Her live show is crazy amazing and full of energy. I included what I teel is her best song on this list. Gunpowder & Lead is not your momma’s song. It’s in-your-face attitude and this chick isn’t taking anything from any man. Pay attention or you’ll get kicked in the teeth, men.

30. I Couldn’t Leave You If I Tried – Rodney Crowell

Rodney Crowell may be an artist a few people will forget about. When it comes to remembering big events though we have to remember that Rodney strung off five straight number one hits from one album back in the ’80s. I Couldn’t Leave You If I Tried was one of those top hits and I still love hearing it on country radio. It’s always on the classic channel. Rodney has such a unique sounding voice. He’s a unique kind of country artist and I think he should always be remembered.

29. Cowboy Casanova – Carrie Underwood

Carrie Underwood needed to be on this list. You could argue that Carrie is already the greatest female country artist of all time. She has the sales and the awards to back up the claim. I love this song. It’s original. It’s sassy. There is plenty of attitude and it was a huge hit. I think as time goes on we’ll look back on this as one of Carrie’s best country songs in what will be a huge list of country classics. Carrie is a great artist and no man better two time her. She’ll write a song about you that becomes a country classic.

28. A Broken Wing – Martina McBride

Martina McBride is one of my favorite country artists. Perhaps her most country song was the hit A Broken Wing. The song is the story of a woman trying her best to separate from an abusive, damaging situation. Eventually she is able to break free. She may have the broken wing from the past relationship, but she was strong enough to get out and make her life better. These kind of songs are inspiring for country fans. There is room in country music for more empowering songs like this.

27. Any Man of Mine – Shania Twain

It was difficult picking a Shania Twain song for the list. I went back and forth trying to think about what Shania song was the best country kind of song. She had the occasional song that drifted into pop, which is fine. In the end I came back to the song I remember being a huge, huge hit. Any Man of Mine changed things in country music. Shania brought a sexy attitude to country music. She let women know it was Ok to be sexy and confident. She had swagger before anybody even knew who Fergie was. A great song from a brilliant artist.

26. Don’t Take The Girl – Tim McGraw

Tim McGraw had his first hit with Indian Outlaw, but it was his second hit single that really turned him into a household name. Don’t Take The Girl became a number one song on the country singles charts. It was about the devotion and love for a woman. Through a few difficult situations a guy is always willing to give up anything in his life as long as he didn’t have to give up his love. That’s devotion and the story along with the sing along lyrics made for a great country song. It’s been one of those songs where in my experience you can even find college age guys sing along to it with each other when it comes on the stereo. Quite the sight.

25. John Deere Green – Joe Diffie

There is a theory in country music that if you can get the kids to sing along with the chorus of  song you know you’ll have a major hit on your hands. It’s not as easy at it sounds. Kids are particular and honest in their assessment of just about anything including music. One of those songs that every kid and adults knows is John Deere Green by Joe Diffie. It’s a song about a good old country boy declaring his love for Charlene by writing their names on the water tower…in John Deere Green of course. It was the combination of that story with a great hook and melody that made this a best country song.

24. Highway 40 Blues – Ricky Skaggs

Ricky Skaggs combined some bluegrass with modern country songs in the ’80s. A string of top hits came to Ricky during his heyday including the classic Highway 40 Blues. It was pretty amazing for a bluegrass kind of guy to find such big success in country music, but Ricky’s talent couldn’t be denied back then. The song was about life on the road yet it became a song the fans loved. Country music needs more artists like Ricky Skaggs these days and more of the best country songs like Highway 40 Blues.

23. Don’t Close Your Eyes – Keith Whitley

Keith Whitley was involved in country music from a young age. He worked his way up through the ranks playing in bands and eventually working his way to a solo career. After a few albums he gained more control of his music and then struck gold with a record that included the huge hit Don’t Close Your Eyes. The song was genius. It was a new kind of songs about relationships, love, and fading love. The song remains popular even today on radio and reminds country fans that Keith Whitley left us too early.

22. Set ‘Em Up Joe – Vern Gosdin

Vern Gosdin was known as one of the greatest in country music history. He racked up hit after hit, but I had to include this classic about an old Ernest Tubb song. The song is about a man lost without his woman. She left and know he’s stuck in the bar playing the same record over and over on the jukebox. He comforts himself with the fellow bar patrons and downs a few cold ones to forget about his woman. It’s the classic kind of country song that makes you love country music. One of the best.

21. Meet In The Middle – Diamond Rio

This is one of my favorite songs of all time. I actually have Diamond Rio’s 16 Biggest Hits in my truck right now. I don’t know what it is about Meet In The Middle, but it’s truly one of the best country songs of all time. I love the guitar part and I thought it sounded difficult to play even though my girlfriend informed me that it wasn’t. I think it’s still catchy and melodic regardless. The story of the song is great. It’s about a couple always finding compromise in an individual world. Diamond Rio is a great band and this song is still a highlight of their live show.

20. Five Minutes – Lorrie Morgan

Lorrie Morgan lived a country song. Through numerous loves and loves lost Lorrie has breathed and soaked in just about every country lyric. With all of that authentic background Lorrie made people feel her songs. One of Lorrie’s biggest hits was Five Minutes. The song was about a woman that was fed up with her man. He was begging and pleading for one last chance and Lorrie finally relents and gives him just five minutes to make his case. It doesn’t look good though. This is a strong woman.

19. As Good As I Once Was – Toby Keith

Toby Keith has had so many hits over the  last 15 plus years that it’s hard to pick the best one for this list. I had to go with As Good As I One Was though. The song seemed to have an impact on so many guys that were…reaching their later years. After a while things slow down. Life gets a little more relaxed, but even though some guys can’t do what they could way back in their younger days they still have enough in the tank to get things done for one attempt. Don’t count out the experienced guy in the crowd.

18. There Goes My Life – Kenny Chesney

Kenny Chesney someone took his career into the rockstar level when the turn of 2002 came around. He had been around for years in the country world and had racked up enough hits for a Greatest Hits collection. For some reason though Kenny got a hold of some good songs and turned his career into something huge. During his big run Kenny found a song that really caught the attention of fans. There Goes My Life is about the things in life (like kids) that can take you by surprise and turn a seemingly bad situation into something amazing. It made for a great song and an amazing moment in country music.

17. Don’t Let Our Love Start Slippin’ Away – Vince Gill

Vince Gill seemed to have it all in his career. The man had more talent that anybody when he first came out on the scene. He could play guitar better than anybody. He had a unique voice that was sent from the heavens and he could write songs better than just about anybody else. A winning combo right? Well it took Vince a few years, but he rocketed to stardom in the ’90s. One of his biggest hits was Don’t Let Our Love Start Slippin’ Away. The track is catchy and a reminder for all those couples struggling that you’ve gotta stick with it when you know the only thing that really matters is your love for each other.

16. Ocean Front Property – George Strait

He had the big records before, but in 1987 George Strait really moved into superstardom with the record and song Ocean Front Property. The album sold more than any of his previous records and the song hit the top spot…of course. Every George Strait song becomes #1 it seems. The track was about a guy trying to admit that he’s not over his lover. He tells her that if she really believes he’s over her he’s got some ocean front property in Arizona for her to purchase. A nice little lyrics that turned into a cliche in the years since. Now that’s powerful.

15. Mama Tried – Merle Haggard

This song always has to be included on best of lists. Merle Haggard is an absolute legend. Merle is mentioned by just about all contemporary country stars for the influence he had. The songs Merle created had something that is often difficult for other songwriters and singers to capture – honesty. With Mama Tried Merle was admitting that he was the rebel child his mama couldn’t control. It wasn’t her fault though and that’s the key issue. He was always to blame. I remember hearing this song on the classic station one day and my uncle looked over and said, “That’s my song.” A great country moment.

14. Forever and Ever, Amen – Randy Travis

Here is a song every country fan has heard. It’s been a classic since it first came out. It’s actually one of those songs that has probably always sounded like a classic even when it was fresh on the radio waves. Randy Travis was a complete throwback to the traditional country singers of the ’40s, ’50s, and ’60s. His style was pure country and it came across in his best songs. This classic track was his signature song. It was pure, wholesome and something everybody could shoot for when it came to loving relationships.

13. Statue of a Fool – Ricky Van Shelton

With five platinum and four gold albums Ricky Van Shelton often gets overlooked in the scheme of country music. For a time in the late ’80s and early ’90s Ricky ruled the singles charts. His voice was so crisp and pure. He had spent hours and hours in the basement of his house training his voice to sound perfect. The hard work paid off and Ricky had one of his biggest hits with Statue of a Fool. The song was a remake of a country classic, but Ricky made it his own. This track is not to be overlooked in the best country song lineup.

12. Chattahoochee – Alan Jackson

Alan Jackson had the summer song of 1993 with this classic and signature song. Alan strapped on a pair of water skis for the video and got back to his roots. Alan was always the best at pulling memories from his past and putting the stories to song. The uptempo track was catchy and fun and people took to it. Even today people love hearing the song and can picture themselves out on the town on a Saturday night in the middle of summer. You can still grab a snow cone and burger today if you find the right place on Saturday night.

11. Small Town Saturday Night – Hal Ketchum

Hal Ketchum burst onto the country scene back in 1991 with a huge first hit single. Small Town Saturday Night had the perfect music for the mood of the song. Teenage angst. The need to get out of the small town you grew up in came through every lyric and every musical beat in this track. Every kid that grew up in a small town dreamed of bigger things at one point or another. Even if we always go back home there is a part of us that just wants to get out on Saturday nights. A dollar’s worth of gas in the pickup and let’s see how far we can go…

10. A Better Man – Clint Black

Clint Black’s career got off to a fast start in 1989. His first single, A Better Man, became one of the top songs of the year. The mid-tempo track was about a guy moving on from a relationship. Sure, he was sad about what happened, but he’s thinking he’ll be a better man for having loved the woman. No ill regard toward her. He’s ready to move on though. It’s a great song that’s really defined by its great melody. I’ve always been drawn to this song and it remains one of my favorites today.

9. Strawberry Wine – Deana Carter

In 1996 a girl next door emerged on the country scene. It was unusual for a record label to release a slow song – a waltz nonetheless as an artist’s first single. That was just what happened with Deana Carter and the result was a classic country song. Strawberry Wine became the biggest hit in country music in the fall of ’96. I can remember hearing the song on the radio every hour of the day and women everywhere were still calling in to the stations to hear it more. The coming of age story became relatable for women all over and the bittersweet nature of the song reflected life perfectly. Truly one of country’s best hits.

8. Hey Good Lookin’ – Hank Williams

It’s one of the oldest songs on the list, but Hey Good Lookin‘ deserves a spot no matter what the time. Hank Williams is considered the father of country music in many regards. His classic song about a good looking woman is simple, but just about every person age five to age ninety-five knows the words. The song remains popular some fifty or sixty years after it was first famous. It’s a timeless song that will be around for many more years.

7. Always On My Mind – Willie Nelson

Willie Nelson wasn’t the first to record Always On My Mind, but his version became a huge hit in 1982. Willie took the track and made it his own. His waning, struggling voice made the song a classic. Willie’s version gave the song critical and award winning praise in the country industry. The song became a Willie Nelson standard. That’s a pretty big achievement for a song in a collection as immense as Willie’s. All the more reason to include it on the best country song list.

6. Crazy – Patsy Cline

The song was written by Willie Nelson, but it was Patsy Cline’s version that was etched into the memories of millions of music fans. Patsy rose to fame with only a few, but huge hits back in the early ’60s. Crazy is perhaps her best and most well known song from her reign. The song is simple in lyric, but that is where the beauty lies. Patsy voice became the star of the song and that is what her fans wanted to her. She was one of a kind and left us too soon.

5. He Stopped Loving Her Today – George Jones

When you ask country fans what they think the best country song of all time is they’ll often cite George Jones and He Stopped Loving Her Today. The track came out as George was actually on a slide in his career. The song turned things around in a big, big way for George. The Possum was nearly fifty when the song came out, but it didn’t matter. The track about a guy that didn’t stop loving his woman until the day he died is amazing and fans loved it. It’s truly one of the best songs of all time.

4. Folsom Prison Blues – Johnny Cash

Johnny Cash had to make it near the top of the list. Cash was the man. He saw a resurgence in his career when the award winning biopic came out just a few years back. That movie revived what many hardcore country fans already knew – Johnny Cash could write and sing a country song. Perhaps the most revered Johnny Cash song was Folsom Prison Blues. The sound of the song sets it apart. The freight train groove and the story of an inmate stuck there wasting away. It all came together and somehow worked for the listeners. A great country track.

3. Behind Closed Doors – Charlie Rich

A bit of a wild card song? I’ll give you that. Charlie Rich did have a huge hit back in the early ’70s with this track. The song was romantic and sultry. There was romance to be had behind the closed doors way back when. Old Charlie won numerous awards and saw his career launched into new heights after this song came out. He had a great run the rest of the decade and then things faded off as he heading into retirement. The track was his biggest hit and one that deserves a spot high on the best country song list.

2. Friends In Low Places – Garth Brooks

In any barroom and honky tonk across the country you’ll hear Friends In Low Places on the jukebox. You’ll probably see a few guys singing along and getting the entire bar together for the chorus. Garth Brooks recorded the song after Mark Chesnutt, but it was Garth’s version that changed country music. The song still sounds like it would be a huge hit today on radio. Garth played the part of the scorned lover perfectly. He may have lost the girl, but he gained millions of pals in the low places all around the country. For all the friends out there in the low places…be sure to play this one loud.

1. You Never Even Called Me By My Name – David Allan Coe

I had no choice. When the song is awesome and it says right in the lyrics that it’s the best country and western song I have to include it as the number one song on the list. David Allan Coe had a handful of hits on the charts, but none were better or more remembered than You Never Even Called Me By My Name. You can go anywhere in the country and play this song for a group of country folks hanging out on a Friday night and they’ll start singing along with every word. It doesn’t get any better than this song. For all the disrespected people out there – this ones for you. The best country song of all time.