Jason Isbell's 10 Greatest Songs

by Julian Spivey
I’ll be seeing Jason Isbell and the 400 Unit at Robinson Music Center in Little Rock on Sunday (Jan. 21) and it’s a show I’ve been looking forward to seeing ever since it was announced months ago. Isbell is my favorite singer-songwriter of his generation and with each album he releases his legacy within the Americana genre grows and grows. That makes creating a list of his 10 greatest songs an almost impossible task (this is the second one I’ve done over the years – he’s released two albums since the last). His music means so much to me that I honestly have a hard time ranking his best work. I’m 100 percent certain of the top two on this list, but No. 3-10 may as well have been put in a hat and chosen at random. That’s how good he is.

10. Hope the High Road
“Hope the High Road” was the first song I heard off Jason Isbell & the 400 Unit’s fantastic The Nashville Sound album and coming off the incredibly tough 2016 it was the most hopeful thing I could’ve heard. I’m not sure any other chorus spoke to me as much in 2017 as: “I know you’re tired/And you ain’t sleeping well/Uninspired/And likely mad as hell/But wherever you are/I hope the high road leads you home again/To a world you want to live in.” 

---

9. ​Stockholm
Jason Isbell doesn’t do too many love songs, but “Stockholm” from his 2013 album Southeastern is a darn good one. “Stockholm” is probably based on the love of his now wife (and fellow musician) Amanda Shires getting him through the alcoholism he faced. She helped him replace his old love of booze (which he was shackled too) and made him see what true love really could be. 

8. Dress Blues
“Dress Blues,” from Jason Isbell’s debut solo album Sirens of the Ditch in 2007, is the heartbreaking story of an American hero who doesn’t return home from a war that he likely should’ve never been sent to fight in the first place. The song was based on the real-life death of Corporal Matthew Conley, from Isbell’s hometown, who died in the Iraq War. 

7. ​Something More Than Free
Jason Isbell’s follow up to his 2013 stunner Southeastern turned out to be noticeably more upbeat and optimistic than the somber release that appeared on many “best of” list two years ago, but everybody seemed to love it just as much. The title track “Something More Than Free” showed the world that this Americana darling could write something more country and true-to-life than any of those hacks currently releasing records in Nashville. “Something More Than Free” is a true working man’s anthem and something we should all try to strive for. 

6. Cover Me Up
“Cover Me Up,” the 2014 Americana Honors & Awards winner for Song of the Year off Southeastern, is like “Stockholm” in that it was likely born out of Amanda Shires’ love and guidance through a rough time during which Jason Isbell was sobering up from alcohol addiction. The beautiful song, both lyrically and through Isbell’s devastating vocals, details a relationship in which the protagonist needs nothing more than his love. 

5. ​Decoration Day
“Decoration Day,” which appeared on Jason Isbell’s very first album with the Southern Rock group the Drive-By Truckers, is one of those perfect short stories set to music. The Drive-By Truckers must have liked it quite a lot as they named their 2003 album after it. The song tells of a sort of modern day Hatfields & McCoys feud between two families by the name of the Hills and Lawsons and the history of that feud. It’s brilliant work by Isbell as a songwriter and performer. 

4. Songs That She Sang in the Shower
“Songs That She Sang in the Shower,” from 2013’s Southeastern, is an absolutely devastating song about a failed relationship. Southeastern is filled with devastating tunes for various reasons and this one ranks very high on that album. The narrator of the song recalls losing a love to his own stupidity and excesses and how the one thing he absolutely can’t stand since she’s gone is to hear or remember all the songs she used to sing in the shower. 

3. ​Yvette
“Yvette,” one of the real highlights from 2013’s Southeastern, is another dreadfully depressing song from that record, but one that’s beautifully written and performed. The song takes on the important topic of sexual abuse of a minor with the narrator’s classmate Yvette being abused by her father and him setting out to see that he’s done his horrible deed for the very last time. 

2. Outfit
“Outfit,” a favorite of Jason Isbell’s fans, is one of his tracks that came out of his days with the popular Southern Rock act the Drive-By Truckers. The song about a father’s advice to his son leaving home appeared on the Truckers’ 2003 album Decoration Day, his first of three albums with that group before setting out on his own (or rather being fired when his alcoholism at the time caused problems). “Outfit” is proof that Isbell’s been one of this country’s very best singer-songwriters going back as far as a dozen years. 

1. Alabama Pines
Jason Isbell’s “Alabama Pines” from his 2011 album Here We Rest is quite possibly the best song written of any genre in the last half decade – even though many have likely never heard it due to Isbell’s Americana genre not getting any airplay whatsoever on mainstream radio. “Alabama Pines” is loneliness and desolation defined in its exquisitely crafted verses that truly speak to the hearts and minds of those who’ve experienced similar things to what the song’s narrator is going through. The perfect vocals from Isbell, whose voice is truly a revelation, will knock you off your feet.