Chris Stapleton's 10 Best Songs: Critic's Picks

Andy Barron
Chris Stapleton

In the past two years, the music of Chris Stapleton has taken over the country music landscape. The Kentucky-born singer is proof that sometimes, the cream does rise to the top. He is as unlikely of a "star" as anyone in the genre, and that is further proof of why he’s so good -- he’s simply real.

In taking a look at Stapleton’s two albums, and analyzing his best work so far, it’s worth noting that his most memorable work all includes thought-provoking lyrics -- some that include a lot of self-realization about the mistakes that one has made in their life. In other words, Chris Stapleton makes us think -- and that’s a sure-fire example of an "artist" rather than just a singer. Here are ten Chris Stapleton songs that easily fit that description!

Best Songs: Alabama | Alan Jackson | Blake Shelton | Brad Paisley | Carrie Underwood | Dierks Bentley | Dolly PartonEric Church | George Jones | George Strait | Jason Aldean | Johnny Cash | John Denver | Keith Urban | Kenny Chesney | Kenny Rogers | Lady Antebellum | Miranda Lambert | Rascal Flatts | Reba McEntire | Shania Twain | Tim McGraw | Toby Keith | Willie Nelson | Zac Brown Band

10. Chris Stapleton - "Parachute" 

A prime example of how Stapleton operates as a songwriter -- taking an age-old sentiment (this time of how he aims to be a rock for his lover, a shelter in a storm), and turning it into something new and uniquely different. One of the many gems off of Traveller.

9. Chris Stapleton - "Broken Halos" 

Old friendships never die. This song is proof of that. Stapleton co-wrote this moving track off of From A Room, Volume 1 with Mike Henderson, whom he worked so well with during his days in The SteelDrivers. Making this song even more glorious are the spellbinding harmonies of wife Morgane, who should have a deal of her own -- and likely will soon.

8. Chris Stapleton - "Either Way" 

A Chris Stapleton song that has been around for a while. Lee Ann Womack cut it in 2008 for her excellent disc Call Me Crazy, and Stapleton recorded the song on his 2017 release, From A Room, Volume One. The lyrics are a sobering look at a couple who know that the time has come to end the relationship, but they keep putting off the inevitable.

7. Chris Stapleton - "Tennessee Whiskey"

The breakout hit from his first album featured the singer breathing a bluesy element into a 1980s hit from George Jones. The song sounded a lot different in Stapleton’s hands, and made waves in Nashville throughout the summer of 2015, following the release of Traveller. Of course, that was nothing compared to the night of the CMA Awards that year, where the performance of this song with Justin Timberlake -- and a huge night awards-wise -- effectively put Stapleton on the map!

6. Chris Stapleton - "Nobody To Blame" 

The song that became his first top ten single on the Country Airplay charts, this Stapleton performance featured the singer lamenting the end of a relationship, knowing that it was his fault -- and his alone.

5. Chris Stapleton - "Fire Away" 

Typically, a Chris Stapleton song doesn’t need a video. However, the clip for this sobering composition was one that shone a light on mental illness with a woman’s repeated attempts to commit suicide. The song could have survived on its' own merits, but the video for this one was one of the singers’ finest moments.

4. Chris Stapleton - "Might As Well Get Stoned" 

Perhaps a moment off of his first album that is more of a straight-ahead blues number than a country one, hearing the singer perform this at the Ryman on his Traveller tour -- or any other theater similar in scope or acoustic -- was a musical tour de force where Stapleton showed why he is the current Gold standard.

3. Chris Stapleton - "Sometimes I Cry" 

You might wonder sometimes if Stapleton’s wins or critical acclaim in the industry is a product of record industry hype. But, when you hear this four-minute performance, you don’t have to wonder anymore. With a vocal as heartfelt and as distinctive as anyone else in Nashville today, it’s pretty much a safe statement to say -- he really is that good.

2. Chris Stapleton - "Traveller" 

The title cut from his breakthrough album, this song served notice that Stapleton was like nobody else on the market today. A mid-tempo number that shone the light on his unique vocal approach, this was a welcome addition to the airwaves in the spring of 2015.

1. Chris Stapleton - "The Devil Named Music"

In our opinion, this underrated jewel off of Traveller is perhaps the finest example of just what Stapleton represents as a songwriter. The telling lyrics about a man who lives for that stage experience on the road -- but wonders if the gain is worth the cost -- raises a question that we all have asked about ourselves about our own lives in one way or another over the years. As genius of a song as Stapleton has ever written -- for himself or anyone else.