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

20 Best Chris Stapleton Songs of All Time

Chris Stapleton is a powerhouse in the world of country music, known for his soulful voice and exceptional songwriting. With a discography filled with hits, it’s a tough task to narrow down the 20 best songs from his impressive career. In this blog, we’ll take a closer look at some of his most outstanding tracks, highlighting the unique qualities that make each of them special.

“Tennessee Whiskey”

Stapleton’s rendition of this classic song showcases his rich, bluesy vocals, and the emotional depth he infuses into every note.

“Fire Away”

This ballad is a heartfelt exploration of love and pain, with Stapleton‘s powerful voice delivering raw emotion.


A feel-good anthem with a catchy melody, showcasing Chris’s versatility as a musician.

“Broken Halos”

A touching tribute to loved ones lost, filled with poignant lyrics and Stapleton’s signature gritty vocals.


Millionaire” a sweet and tender love song, revealing the softer side of Stapleton’s songwriting.

“Might as Well Get Stoned”

A bluesy track with a laid-back vibe that’s impossible not to groove along to.


The title track from his debut album, it’s a tale of life on the road and self-discovery.

“I Was Wrong”

A heartfelt apology set to music, showcasing Stapleton’s ability to bare his soul through his lyrics.

“Second One to Know”

A rock-infused, high-energy song, demonstrating Chris’s versatility and range.

“Whiskey and You”

A heart-wrenching ballad filled with longing and regret, a Stapleton fan favorite.

“Either Way”

An emotional powerhouse that showcases Stapleton’s vocal prowess and songwriting depth.

“Outlaw State of Mind”

A gritty, outlaw country track that’s perfect for a road trip playlist.

“Death Row”

A haunting, bluesy song with dark, brooding lyrics, showcasing Stapleton’s storytelling abilities.

“What Are You Listening To?”

An introspective ballad exploring the power of music to heal and connect.

“The Ballad of the Lonesome Cowboy”

A standout from the Toy Story 4 soundtrack, this song captures the essence of the old west.

“Starting Over”

The title track from his album, it’s an anthem of resilience and new beginnings.

“When I’m with You”

A love song that’s tender and heartfelt, showing another dimension of Stapleton’s artistry.

“Hard Livin'”

A rollicking, rowdy tune with a driving beat and rugged vocals.


A passionate and bluesy track that will give you chills, and a testament to Stapleton’s vocal prowess.

“Last Thing I Needed, First Thing This Morning”

A melancholic song that captures the bittersweet feeling of waking up alone.

Frequently Asked Questions

Is “Tennessee Whiskey” considered the best Chris Stapleton song of all time?

“Tennessee Whiskey” is undeniably one of Chris Stapleton’s most iconic songs, but the list includes a variety of his best work to showcase the range of his musical talent. While it’s a standout, there are other equally exceptional tracks in his discography.

What makes Chris Stapleton’s songwriting unique in the world of country music?

Chris Stapleton’s songwriting stands out due to its raw emotion, honest storytelling, and the way it connects with listeners on a personal level. His lyrics often delve into universal themes of love, loss, and self-discovery, making them relatable to a broad audience.

Are there any underrated Chris Stapleton songs that didn’t make the list?

While we’ve highlighted 20 of the best Chris Stapleton songs, there are many more hidden gems in his catalog. “Underrated” can vary from person to person, and we encourage listeners to explore his entire discography to find their personal favorites.

How has Chris Stapleton influenced the country music genre?

Chris Stapleton has had a profound impact on country music by infusing it with elements of blues, rock, and soul. He’s brought a fresh, gritty authenticity to the genre and broadened its appeal to a wider audience, helping to redefine contemporary country music.

What’s the best way to enjoy these top Chris Stapleton songs?

The best way to enjoy these songs is to immerse yourself in the music, paying close attention to the lyrics and the raw emotion in Chris Stapleton’s vocals. Whether you’re listening on a road trip, at a concert, or in the comfort of your own home, his music is best experienced with an open heart and an appreciation for his incredible talent.

Chris Stapleton’s music transcends genre boundaries and touches the hearts of fans across the world. These 20 songs represent some of the finest moments in his career, each one a testament to his songwriting and vocal talent. Whether you’re a die-hard Stapleton fan or just discovering his music, these songs are a perfect starting point for your musical journey with this extraordinary artist.

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