10 Best Chris Stapleton Songs of All Time, Ranked 2023

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Country music is one of those genres that has no shortage of superstars – the selection is often overwhelming, but you simply cannot beat Chris Stapleton. With almost 200 original songs to his name, six number-ones, and a ton of best-selling albums, the popularity of this dude’s music says it all.

Recently, I met a friend who claimed he had no idea who he was, and I was so shocked that I decided that I would put this list together of the best Chris Stapleton songs. 

You probably know all about him already, but if you don’t, trust me – you’re going to want to read this. 

1. Tennessee Whiskey

The first song on my list of the best Chris Stapleton songs is “Tennessee Whiskey”, a moody track that has so much more to give than your typical country songs. People often associate country with happy-go-lucky feelings without too much substance, but this song puts that myth to bed.

Seriously, the soulful and bluesy elements of this song are just such moods. Anyone who tells me that country is substanceless should hear this track, cos their mind is about to be blown.

2. You Should Probably Leave

A lot of Chris Stapleton’s songs are so memorable to me due to the emotions that they provoke. Like the last track, many of his songs just hit deep in a certain area of the feels, and “You Should Probably Leave” is a golden example of this.

I first heard it when I was driving home from a long and slightly sad inter-state visit at my ex-girlfriend’s place that did not end too well. I’m happily married now and it was a long time ago, but listening to this song never fails to bring up some emotions of closure and sadness. 

3. What Are You Listening To

Next up on my list of the best Chris Stapleton songs is “What Are You Listening To”, a beautiful track from the artist’s 2013 album of the same name. This song illustrates perfectly what I was just explaining, the way that the lyrics and mood of a song can just take you to another place. 

The lyrics of this particular song talk of “listening to a sad song on the radio”, it’s kind of ironic actually as it perfectly illustrates “You Should Probably Leave” through an entire song. The depth of this man’s musical concepts is fantastic, really. 

4. Broken Halos

One of the more recent Chris Stapleton songs that I admire is “Broken Halos”, written and released in 2017. In an interview around the same time, Stapleton states that this song was written in the honor of all of the people that passed aware before their time had come.

From musicians such as Curt Cobain to personal loved ones, everyone has someone close to their heart which this happened to. It’s a sad state of affairs, but to have Stapleton write about the feeling makes everything a little more tolerable. 

5. Starting Over

Chris Stapleton has released his music in all sorts of different ways. From epic music videos to audio-only releases, it doesn’t really matter what he does as I know that I will always listen to it.

However, I recent release format that I have really enjoyed is that found in the studio music video for “Starting Over”. Across this video, our eyes are graced with real-time footage of Stapleton performing this beautiful piece of music, tuning his guitar, and jesting with friends. 

It results in a natural and organic atmosphere that is often difficult to come by in music videos. 

6. Millionaire

“Millionaire” is one of the best Chris Stapleton songs that I have ever heard, hands down. The lyrics are all about how the richness of love and friendship is far more important than the lucrative riches of money and fame, something I have found very humbling about the musician. 

I was listening to this on YouTube the other day when I saw an astounding comment – Stapleton’s music teacher from school expressing her delight at how far his musical passion brought him. Now if that doesn’t make you rich in heart, I don’t know what will! 

7. Parachute

https://www.youtube.com/watch?v=pl4c0kZUm2M

Have you ever found that some songs just want to make you jump in your car and drive? With no destination in sight, imagine just driving and driving straight to your heart’s content, with your only goal being to meet someone or discover something new… 

This is exactly how Chris Stapleton’s song “Parachute” makes me feel. Inspired to travel, keen to escape from the rat race, and with a heart full of euphoria. It’s a stunning song that is a little bit heavier and more intense than many of his others, one of the best Chris Stapleton songs in my books. 

8. Fire Away

Music is a fantastic way to heal the soul – there’s no feeling quite like putting your favorite release on the record player and kicking back to some emotional vibes after having a hard day at work. 

Sometimes though, days are tougher than this, and songs such as “Fire Away” are needed over the usual choices. Just take a look at the comments and the number of people this song has helped through tough bouts of depression, breaks up, and grief. It truly is like musical therapy. 

9. Joy Of My Life

The vast majority of Chris Stapleton’s songs are of his own creation. The musician is known for his incredible talent for songwriting, so there’s no wonder why he tends to stick to his own writing other covers.

With that being said, there are certainly exceptions out there, such as “Joy of My Life” originally written by John Fogerty. Something I really appreciate about this cover is that not only did Stapleton cover it beautifully, but he clearly tried to represent the vibe and production style that Fogerty was going for two decades ago. A beautiful tribute. 

10. Traveller

Time sure does fly by when you’re having fun, and in what feels like a click of the fingers, we are already at the end of this list of the best Chris Stapleton songs. I wish I could stick around for longer, but you’re on your own from here – not before I mention “Traveller”, of course.

In my opinion, this is perhaps the most iconic track on this list. It features Stapleton’s classic harmonies with female backing vocalists, slide guitar, feel-good lyrics, the whole shebang. 

It may be a bit simpler than some of his other tracks, but I just think it encompasses the musician’s style perfectly. Emotionally driven, powerful, and relatable to all. A 10/10 track, and I challenge you to make me think otherwise!