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13 Best Chris Stapleton Songs of All Time (Greatest Hits)

December 22, 2023
Chris stapleton songs

I’ve compiled a collection of the best Chris Stapleton songs of all time, showcasing the greatest hits that have cemented his status as a modern country music legend.

This article celebrates Stapleton’s soulful voice and powerful songwriting that resonate with fans across genres.

Top Chris Stapleton songs of all time

  • “Tennessee Whiskey”
  • “Broken Halos”
  • “You Should Probably Leave”
  • “Whiskey And You”
  • “Daddy Doesn’t Pray Anymore”
  • “Millionaire”
  • “Fire Away”
  • “A Simple Song”
  • “Sometimes I Cry”
  • “Starting Over”

1. “Tennessee Whiskey”

Chris Stapleton’s “Tennessee Whiskey” is a timeless classic that continues to captivate audiences around the world.

This smooth and soulful ballad takes listeners on a journey through time and emotion, drawing them in with its romantic yet melancholy lyrics.

Its catchy melody and powerful instrumentation are constants throughout the track, and the combination of Stapleton’s raw vocals and heartfelt delivery make for an unforgettable song.

With its classic country-rock vibe, it’s no wonder why “Tennessee Whiskey” is one of the most beloved songs from Chris Stapleton‘s catalog.

This timeless classic will always remain one of the greatest hits from one of country music’s greatest singers.

2. “Broken Halos”

“Broken Halos” has become one of Chris Stapleton’s most beloved tracks, and rightfully so.

It’s a song that speaks to the beauty of life, even in its broken pieces.

Its delicate melody carries an emotional weight, bolstered by Stapleton’s powerful voice.

The lyrics are painfully honest, acknowledging the harsh realities of life but reminding us that we can still find joy within them.

This song is a perfect example of why Stapleton remains one of country music’s greatest artists – it conveys emotion like few others can, inspiring listeners to look for the light in the darkness.

“Broken Halos” is truly unforgettable and will remain a fan favorite for years to come.

3. “You Should Probably Leave”

If you’re a fan of Chris Stapleton, then you’ve probably already heard his hit single “You Should Probably Leave”.

It’s an infectious track that has been gaining traction on country radio stations across the country.

With its upbeat tempo and catchy lyricism, the song is sure to get your toes tapping.

At its core, it’s a story about someone who knows when it’s time to move on from a relationship.

The clever wordplay and clever guitar licks make for a great listening experience that will leave you feeling empowered and inspired.

So crank up the volume and tap into this empowering anthem – you won’t regret it!

4. “Whiskey And You”

Leaving is hard, but it doesn’t have to mean goodbye.

Chris Stapleton’s ”Whiskey and You” captures the bittersweet feeling that comes with a necessary separation.

This classic country track speaks to the heartbroken, letting them know that even though they may be apart, their love will never fade.

Stapleton’s deep baritone vocal delivery is a beautiful compliment to his passionate lyrics about longing for someone you can no longer be with.

The combination of sorrowful instrumentation and heartfelt lyrics makes this song one of his most beloved hits – and it’s easy to see why.

Even if two people can’t be together in person, they can still keep each other close through the shared memories of a song like ”Whiskey and You”.

5. “Daddy Doesn’t Pray Anymore”

Chris Stapleton’s “Daddy Doesn’t Pray Anymore” is a powerful, emotional track that speaks to the hearts of many.

It’s an honest look at how life can sometimes change drastically and quickly, leaving us feeling helpless and alone.

The song perfectly captures the sentiment of those times with its moving lyrics and Stapleton’s unique voice.

It’s a reminder that, even in our darkest hours, we can still draw strength from our faith and loved ones.

This song has been embraced by fans all over the world who have found comfort in its message of hope and resilience.

Its timelessness makes it one of Stapleton’s greatest hits and a must-listen for any music fan looking for an uplifting anthem.

6. “Millionaire”

Switching gears, Chris Stapleton’s “Millionaire” is a song that will be sure to stay with you after listening.

The song highlights the importance of true love and how it can’t be bought, even if you’re a millionaire.

It speaks to the listener on an emotional level, with its catchy melody and soulful lyrics.

Stapleton has once again proven why he is one of the greatest country singers of all time with this track.

His ability to write meaningful songs that connect with people is what makes him truly special – and “Millionaire” does just that.

By using metaphors and clever lyricism, he brings his listener’s attention to what really matters in life: love.

7. “Fire Away”

Moving to the uplifting spirit of “Fire Away”, Chris Stapleton has created a masterpiece that speaks to the heart.

This song is one of his most popular and for good reason.

Its lyrics are powerful and passionate, touching on themes of love, hope, and redemption.

The instrumentation is dynamic and captivating, combining electric guitar riffs with soulful acoustics for an unforgettable sound.

“Fire Away”‘s message is one of strength and courage in the face of adversity; it encourages us to fight for what we believe in and never give up.

It’s no wonder that this song continues to be one of Stapleton’s greatest hits – its deep emotion reaches out to listeners everywhere with a liberating message that resonates long after the music stops.

8. “A Simple Song”

Chris Stapleton’s “A Simple Song” is a timeless classic that never fails to tug on the heartstrings.

It starts off with a bluesy twang of guitar and builds up to an emotional crescendo that speaks to the soul.

The lyrics are simple but profound, conveying the message that life isn’t always as complicated as we make it out to be.

Stapleton’s voice soars across every verse and chorus, making this song a staple in his discography.

It’s an ode to living simply and enjoying the little things in life, something we all could use a reminder of sometimes.

Whether you’re driving down the freeway or sitting at home on the couch, “A Simple Song” will bring a sense of peace and joy into your life.

9. “Sometimes I Cry”

It’s no surprise that Chris Stapleton’s song “Sometimes I Cry” is one of his greatest hits.

With its soulful lyrics and powerful delivery, it captures the essence of what it feels like to be overwhelmed with emotion.

This track is a great reminder that even when life gets tough, it’s okay to let your tears flow freely.

Every line in this song carries with it a profound message about human resilience and perseverance in the face of adversity.

In short, “Sometimes I Cry” is an anthem for anyone who has ever felt like they can’t keep going on their own – a testament to the power of collective strength and support.

10. “Starting Over”

From the wrenching lyrics of “Sometimes I Cry” to the inspiring energy of “Starting Over”, Chris Stapleton has proved time and time again why he’s one of the greatest country music singer-songwriters of all time.

The title track from his fourth studio album Starting Over is a perfect example of his signature soulful country sound, as Stapleton’s passionate vocals soar over a driving beat.

With its uplifting message, this song celebrates the beauty and joy that can be found in starting anew.

It encourages us to let go of past mistakes and take risks, reminding us that life is full of possibilities if we just have faith.

This song brings hope to anyone feeling stuck in life, a reminder that no matter how hard things get, it’s never too late to start over again.

11. “Second One To Know”

Chris Stapleton is a master at tugging the heartstrings of listeners, and his song called “Second One to Know” from his 2017 album From A Room: Volume 1 is no exception.

It’s a powerful reflection on living life with joy, even when you don’t get the immediate recognition you feel you deserve.

There’s a deep sense of loss that’s balanced by an even deeper understanding of hope — one that can only be found in those who have endured tough times but come out on top.

The instrumentation beautifully underscores Stapleton’s heartbreaking lyrics, and the result is an anthem for anyone who has ever felt overlooked or underappreciated.

There may be moments of sadness throughout this song, but its message is ultimately a comforting one: no matter what life throws your way, always keep fighting.

12. “Nobody To Blame”

Switching gears from the comforting country tones of “Second One to Know” is Chris Stapelton’s hard-hitting number “Nobody to Blame”.

Full of attitude and power, this song stands as an anthem for those who have been wronged in life and are looking for a way to take back control.

The lyrics tell a story of personal struggle and determination, as Stapleton’s twangy vocals declare that you can’t blame anyone but yourself for your own fate.

It’s a powerful message that resonates with listeners, providing an inspiring glimpse into resilience – no matter what life throws at you, you always have the power to pick yourself up and keep going.

This song will stay with you long after it ends, reminding you that nobody has the power to stand in your way if you’re determined enough.

13. “Cold”

Chris Stapleton’s song “Cold” is a must-hear for any fan of the artist.

This track, released in 2019, is a perfect example of why he’s become a modern country music icon.

With its smooth guitar tones and Stapleton crooning memorable lyrics like “It ain’t getting warmer, just colder by the day”, you can feel the emotion in every line.

He takes us on a journey through heartbreak and sorrow while also reminding us that it’s important to keep our heads high no matter what life throws at us.

The inclusion of elements like a soulful piano melody and gospel choir backing vocals make this song stand out as one of his best.

It’s clear that Chris Stapleton knows how to bring out the best in his music and create something truly special with “Cold”.

Best Chris Stapleton Songs – Final Thoughts

I’m sure that I could go on and on about Chris Stapleton’s amazing music.

His songs have a unique blend of country, blues, and rock that can’t be matched.

Whether you’re looking for an emotional ballad or a foot-stomping jam, there’s something in his catalog for everyone.

Chris Stapleton is one of the most talented artists in the industry today, and these fifteen songs are just a few examples of why.

He has the ability to create timeless classics like “Tennessee Whiskey” and “Whiskey and You”, as well as more modern hits like “You Should Probably Leave”.

So if you’re looking for some new music to enjoy, I highly recommend checking out Chris Stapleton’s greatest hits!

Will Fenton

Will, the founder of MIDDER, is a multifaceted individual with a deep passion for music and personal finance. As a self-proclaimed music and personal finance geek, he has a keen eye for futuristic technologies, especially those that empower creators and the public.

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