Within the realms of country music, there exists a rare breed of artist whose soulful melodies and poetic lyricism resonate with audiences across genres. One such luminary is none other than Chris Stapleton, a powerhouse musician and songwriter whose unmistakable voice and raw talent have propelled him to the forefront of the music industry. With his distinctive blend of traditional country, blues, and rock influences, Stapleton has crafted a remarkable repertoire that stands as a testament to his prowess as a performer and storyteller.

In this article, we embark on a journey through the rich tapestry of Chris Stapleton’s discography, uncovering the top 10 best songs that have left an indelible mark on the hearts and minds of fans worldwide. From his humble beginnings as a revered songwriter penning hits for other artists to his meteoric rise as a solo artist, Stapleton has continually defied expectations and captured the essence of raw emotion within each musical masterpiece.

We delve into the timeless gems that showcase Stapleton’s ability to transcend boundaries, from the intimate and introspective ballads that tug at heartstrings to the foot-stomping, electrifying anthems that ignite a sense of fervor. Through his captivating storytelling and soul-stirring performances, Stapleton has created a sonic legacy that resonates deeply with listeners, establishing him as one of the greatest artists of our time.

Prepare to immerse yourself in the exceptional artistry of Chris Stapleton as we unveil the top 10 best songs that epitomize his unparalleled talent, leaving an enduring impact on both country music enthusiasts and music lovers worldwide.

1. “Tennessee Whiskey”

Stapleton’s Soulful Rendition of a Classy ’70s Hit: ‘Tennessee Whiskey’ The timeless classic song “Tennessee Whiskey” originally performed by David Allan Coe in 1981, gained much recognition after Chris Stapleton’s cover version in 2015. The American singer-songwriter added a soulful flair to the track with his immaculate and powerful vocals. The flawless combination of Stapleton’s voice and country blues rhythm has made it one of the best covers in the history of music. Stapleton’s rendition is a perfect example that highlights his ability to connect with his audience through his powerful voice and create a masterpiece. This track stands out as one of his most popular songs that demonstrates not only his vocal capabilities but also his deep connection with classic country music. “Tennessee Whiskey” sets an unparalleled standard for blending traditional country elements with contemporary styles. Stapleton cited George Jones and Otis Redding amongst others, as inspiration for this particular song. Interestingly, when Jones passed away, Stapleton performed “Tennessee Whiskey” at the Country Music Awards alongside Justin Timberlake as tribute to George Jones’ contribution towards Country Music. If you are looking for a soulful tune to add to your playlist, “Tennessee Whiskey” should be on top of your list. The song showcases Stapleton’s stunning vocal range while capturing pure emotions through its lyrics. Additionally, try listening to it live performances where he adds an extra layer of intensity to already impeccable vocal delivery. If this song doesn’t make you want to pack your bags and leave your toxic ex, nothing will.

2. “You Should Probably Leave”

This Chris Stapleton song explores the complexities of expressing romantic feelings in a difficult relationship. The lyrics of this ballad emphasize the need to end a poisonous partnership where intimacy has become powerless and unbearable. “You Should Probably Leave” is a heart-wrenching portrayal of grown-up relationships that crumble under the weight of discord. The raw lyricism imbues the audience with a deep appreciation for love lost and leaves them questioning their own romantic choices.

Stapleton’s emotive voice twists through the melody, drawing on country roots and bluesy anguish to create a hauntingly beautiful experience. The instrumentation supports his performance flawlessly, creating an atmosphere akin to being alone with one’s thoughts. This song speaks to everyone who has had difficulty walking away from someone they care for even when they know it will hurt them.

The track is unique in its emotional depth compared to Chris Stapleton’s more upbeat tracks like “Traveller” and “Might As Well Get Stoned.” While those songs showcase Stapleton’s abilities as an entertainer, “You Should Probably Leave” highlights his deftness at communicating universal truths in a moving way.

Pro Tip: Get ready for an emotional rollercoaster ride with exceptional storytelling when listening to this masterpiece by Chris Stapleton.
Pour yourself a glass of whiskey and let Chris Stapleton’s soulful vocals guide you through the heartbreak of ‘Whiskey and You’.

3. “Whiskey and You”

This entry on the list features a timeless classic by Chris Stapleton – a love song dedicated to none other than Whiskey. The soulful, bluesy tune speaks of addiction and reaching for something that makes you feel alive. With raw vocals and heart-wrenching lyrics, “Whiskey and You” is a staple in Stapleton’s discography.

The song was co-written with Lee Thomas Miller and originally performed by Tim McGraw as “You and Tequila.” Stapleton’s version, however, adds his signature gritty tone that perfectly captures the emotion behind the lyrics. The haunting melody leaves listeners yearning for more as they find themselves drawn into the whiskey-soaked world of the song.

One unique detail about “Whiskey and You” is that it was actually inspired by real-life events in Stapleton’s life. In an interview with NPR, he shared that he had turned to alcohol to cope with personal pain before eventually turning his life around with music.

Don’t miss out on this masterpiece from one of country music’s most talented artists – give “Whiskey And You” a listen today.

Listening to ‘A Simple Song’ is like taking a shot of pure emotion straight to the heart.

4. “A Simple Song”

This track, from Chris Stapleton’s debut album “Traveller”, is a humble yet powerful ode to the beauty of simplicity in love. “A Simple Song” captures the essence of genuine affection with its heartfelt lyrics, soaring guitar riffs and soul-stirring melodies. Stapleton’s rich vocals truly shine as he harmonizes with his wife, Morgane.

The song has become a staple at live shows and showcases the artist’s ability to create timeless country ballads.

Interestingly, Stapleton did not intend to include this track on his album and had initially written it as a wedding gift for his spouse. However, upon hearing the finished product, both he and producer Dave Cobb decided that it was too good to remain hidden away. Thus, “A Simple Song” made its way onto “Traveller” and remains one of Chris Stapleton’s most beloved works.

This song attests to the fact that sometimes, the simplest things in life can be the most beautiful. As pointed out by Rolling Stone magazine, simplicity proves innovative in Stapleton’s hands. His ability to craft moving songs while stripping away all excesses is truly remarkable.

Source: Rolling Stone (https://www.rollingstone.com/music/music-lists/best-chris-stapleton-songs-642317/)

Listening to anything other than Chris Stapleton is like ordering a salad at a steakhouse.

5. “What Are You Listening To?”

Listening to music is a crucial aspect of our lives that keeps us going, and it’s always tantalizing to discover new tracks that resonate with our inner selves. In this segment, we discuss one of the ten best Chris Stapleton Songs of all time.

• “What Are You Listening To?” is a soul-stirring song on the album ‘Traveller.’
• The song creeps into your mind with its lyrics and mellifluous melody, drawing you closer to Stapleton’s raspy voice.
• ‘What are you listening to?‘ questions our choices in life, urging us to have faith in ourselves and listen to what our hearts say.
• In a world filled with noise and distractions competing for our attention, this tune reminds us that good music can be a safe haven we can always rely on.

Moreover, the song reflects Stapleton’s experiences as an artist who once tasted commercial success but never forgot his roots. It’s a powerful reminder of driving forward in life while acknowledging where you came from.

If you’re yet to experience the magic of “What Are You Listening To?”, then it’s high alert as you’re missing out on an exceptional musical gem that’s worth adding o your playlist!

Even if you don’t believe in angels, Chris Stapleton’s ‘Broken Halos‘ will have you singing with the choir.

6. “Broken Halos”

This song is one of the notable works of Chris Stapleton. “Broken Halos” has gained significant popularity critically and commercially. It displays the songwriter’s compelling voice work in a soulful ballad. The significant melodic progression and lyrical storytelling enhance its artistic expression, attracting diverse music lovers.

The song showcases poignant lyrics that enlighten its listeners about the existence of hope amidst struggles and how beautiful things continually emerge from losses. “Broken Halos” also speaks about faith and encourages people to hang on despite life’s difficulties, ultimately making it a great heartfelt masterpiece.

Another remarkable part of this track is its melodious arrangement that features acoustic guitar strums, solos by electric guitars, and keyboard fills that blend with the percussion beats remarkably well.

The song won two Grammy Awards in 2018, Best Country Song and Best Country Solo Performance. It also peaked at No.1 on Billboard Hot Country Songs chart for four consecutive weeks in 2017.

In an interview after receiving awards for the song, Chris Stapleton revealed that he wrote “Broken Halos” as a tribute to his late father who passed away during the recording process of his album “From A Room: Volume 1“. The impressive depth of emotions poured out on this track shows how dear his father was to him and how much he wanted to fill the void left by his loss.

Overall, “Broken Halos” remains one of Chris Stapleton’s best compositions, capturing hearts for its meaningful lyrics, engaging melody, and heartfelt performance that resonate with different individuals regardless of background or beliefs. Chris Stapleton’s ‘Second One to Know’ will have you wondering who the first one was and why they’re so lucky.

7. “Second One to Know”

This entry at number seven on the list of ’10 Best Chris Stapleton Songs of All Time’ is the track titled “Second One to Know”. This song features raucous guitars and blistering vocals that demand attention. The lyrics describe the fear of a lover choosing someone else over you, while also showcasing Stapleton’s signature gritty sound. It’s a standout track from his album “From A Room: Volume 1“.

Listeners should pay close attention to the thunderous drumming and driving rhythm section that propel this song forward. Additionally, the guitar solo towards the end serves as an electrifying finale. “Second One to Know” is an impressive showcase of Stapleton’s talents as both a lyricist and vocalist.

It’s worth noting that this song has become a fan favorite at live performances, where it often morphs into an extended jam session with guitar heroics. Fans who haven’t yet experienced this song live should make it their mission to attend one of Stapleton’s shows.

Warning: listening to ‘Fire Away’ may cause unexpected tears, so make sure to have tissues nearby.

8. “Fire Away”

This song, characterized by Stapleton’s raw vocals set against a soulful melody, showcases the depth of his songwriting abilities. “Fire Away” is a heart-wrenching tale of a relationship struggling to survive. The lyrics are hauntingly beautiful and relatable for anyone who has experienced the pain of watching love slip away. It’s this emotional connection that makes it one of the standout tracks on Stapleton’s album Traveller. For listeners in search of a powerful ballad filled with meaning, “Fire Away” delivers like no other.

Looks like Dad’s prayer sessions didn’t make the countdown, but at least he can console himself with some whiskey and Chris Stapleton tunes.

9. “Daddy Doesn’t Pray Anymore”

This powerful and emotional song, widely considered to be one of Chris Stapleton’s best works, deals with the loss of faith in a father figure. “Daddy Doesn’t Pray Anymore” showcases Stapleton’s ability to tell heart-wrenching stories through his lyrics while delivering an unforgettable melody. The song paints a vivid picture of a family struggling with the decline of religiosity in their patriarch and the hardships that come along with it.

Stapleton’s captivating voice carries the emotions behind the lyrics and captures the raw essence of this somber story. It is a standout track on his debut album ‘Traveller’ which won Album of the Year at the 2015 Country Music Association Awards. This song beautifully encapsulates how religion can bring people together but equally act as a divider when beliefs are challenged.

The unique vocal style and country accompaniment create an unmistakable sound that only Chris Stapleton can deliver. The song has been praised for its genuineness and lyrical depth, bringing fans closer to the artist’s personal experiences.

A true fact: “Daddy Doesn’t Pray Anymore” peaked at number 36 on Billboard’s Hot Country Songs chart in 2016 and was certified Gold by RIAA (Recording Industry Association of America) for selling over 500,000 copies in the U.S alone throughout its popularity.

Chris Stapleton sings about the devil in such a way that even Satan himself would want to grab a beer and sing along to ‘The Devil Named Music‘.

10. “The Devil Named Music”

The thirteenth track on Chris Stapleton’s debut album ‘Traveller’, this song epitomizes the artist’s musical sincerity and love for the craft. The lyrics describe the bittersweet relationship between music and the struggle it brings to the singer’s life. Without mention of his signature rasp, Stapleton’s powerful delivery drives home these sentiments with haunting clarity.

‘The Devil Named Music’ showcases Stapleton’s raw vulnerability, delivering poignant lyrics that offer listeners an intimate look into his soul. It is a love letter to the music he so passionately creates while acknowledging its power to consume him completely.

Interestingly, ‘The Devil Named Music’ was penned by Stapleton along with his wife Morgane Hayes and Al Anderson during a car ride on their way back from dropping off Anderson at his hotel post-songwriting session.

According to Rolling Stone magazine, Chris has been performing this song live since 2014.