15 Best Jason Isbell Songs You Should Hear At Least Once

Jason Isbell songs are known not only for their versatile character but also for their storytelling and poetic lyricism. The Grammy-award winning alt-country singer-songwriter who started his career with the Southern rock outfit Drive-By Truckers in 2001 is now one of the biggest and most successful country music singers of his generation. 

So, we compiled the 15 best Jason Isbell songs – from his early Drive-By Truckers days to his evolution as a solo artist and his collaborations with his now band 400 Unit and wife Amanda Shires. Hop in and listen to these country music gems. 

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1. “Outfit” (2002)

Though the song may be kind of outdated, it’s still a reminder of love shown in good intentions. Outfit was a song born out of a father’s advice – earnest, sly, with a bit of regret. Isbell wrote the song as the guitarist of Drive-By Truckers and is one of the best father-son songs ever.

2. “Decoration Day” (2003)

Decoration Day was written by Isbell shortly after joining Drive-By Truckers as the title track of the album of the same name, which was also his first feature in songwriting. The song, which was fitted with elements of Southern folklore, remains one of his most interesting songs and a staple in his solo repertoire.  

3. “Goddamn Lonely Love” (2004)

The title speaks so loudly for all the feelings you’ll feel listening to this song. Goddamn Lonely Love from the Drive-By Truckers’ Dirty South album is one hell of a heart-wrenching song that painfully tackles the loneliness that comes with love.

4. “Down in a Hole” (2007)

From his impressive solo debut album Sirens of the Ditch, Down in a Hole is a swamp rock saga featuring a rich and ambitious protagonist corroding a small Southern town. The song emphasized lyrical wariness couching it in a character’s advice tuned with a sultry-blues vibe.

5. “Alabama Pines” (2011)

The single that began his resurrection, Alabama Pines is a rebellious tune that describes a drifting soul in moments of rootless desperation and vague yearning of home. The song won him Song of the Year at the 2012 Americana Awards and remained one of the finest songs in his catalogue. 

6. “Go It Alone” (2011)

No one can probably write loneliness better than Isbell, and Go It Alone is definitely one of the concept’s masterpieces. This song is rugged and front loaded with rock n’ roll exhaustion, very much like the touring musician eyeing a weary life alone once the tour ends. The song is credited to him and his band 400 Unit. 

7. “Cover Me Up” (2013)

Honest and vulnerable, Cover Me Up is probably the truest love song he could ever write. He bared himself on this one, talking about his personal feelings and addressing his long-time substance abuse issues. This song has won him the 2014 Song of the Year award at the Americana Music Association Award.

8. “Elephant” (2013)

Elephant is honest, defiant, intimate, painful, humorous, sultry, and sexy all in one. And it was these different flavors of feelings that broke through his listeners. From his critically acclaimed album Southeastern, this song told the heartbreaking story of a man witnessing someone die from cancer, realizing that no one ever really dies with dignity. 

9. “Relatively Easy” (2013)

The last track off his Southeastern album, Relatively Easy, delivers the best punchline to the album. Though the theme of the song is tragic, circling around drug addiction, suicide, loneliness, it offers consolation that on a grander scale of things, our lives are still ‘relatively easy.’ 

10. “Stockholm” (2013)

Isbell’s Southeastern album is undeniably one of his best albums, and unsurprisingly another best song of his is from this album. Stockholm is an elegant and powerful song, a baroque country-rocker, that showed how true worthwhile love could free us from the prison we put ourselves in.

11. “Traveling Alone” (2013)

Another cheer from the Southeastern album, Traveling Alone, is a conversation about healing and recovery. From the depths of rock bottom due to substance abuse, Isbell is talking to his lover Amanda Shires, who had helped him get into rehab. 

12. “24 Frames” (2015)

24 Frames is a gripping truth of existential fear that everyone could relate to, no matter where they are in life. It offers no platitude; only the truth served with empathy. This song won the Best American Roots Song at the 2016 Grammy Awards and is a tribute to the home of his former band, Drive-By Trucker. 

13. “If We Were Vampires” (2017)

From his 2017 album The Nashville Sound, If We Were Vampires is a healthy dose of bittersweet reality, tackling the fact that love can be forever, yet time is finite. This is one of his most critically acclaimed tracks and one that has become so special to many over time. 

14. White Man’s World, 2017

White Man’s World is quite a controversial song where Isbell raised questions about gender and racial injustice while confronting and acknowledging his own privilege as a white male man. The song was inspired by the 2016 Presidential Elections where Trump won and was absolutely one of the songs that showed Isbell’s character as a country singer. 

15. Maybe It’s Time, 2018

Maybe It’s Time is a country ballad that talks about salvation and redemption, this song was penned by Isbell for the 2018 film A Star Is Born, starring Lady Gaga and Bradley Cooper. And this was probably one of the songs in his catalogue that he could confidently say that most people have heard. 

More Jason Isbell songs to check out:

We can never get enough of Jason Isbell’s tunes, so here are 10 more to indulge in. 

Make sure to check everything out! Jason Isbell songs are very much worth the listen, and we promise that you’ll never regret it.