Top 10 Jason Isbell Songs

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Our top 10 Jason Isbell songs list presents ten of the best songs released by an American Grammy Award-winning singer-songwriter famed for his country sound. Born in 1979, Jason Isbell was inspired to play various musical instruments by his uncle and grandfather who lived close to his school. By age six, Jason Isbell already knew how to play the mandolin. He would later learn to play the horn and trumpet while attending high school. As a young man, Jason Isbell was exposed to bluegrass and gospel music.

Jason Isbell started engaging with several young bands in his mid-teenage years, including a country cover band. He was privileged to see David Hood (father to Drive-By Truckers co-founder Patterson Hood) perform in local restaurants. Jason Isbell gained the courage to meet David Hood and other artists, informing them that he was a young musician. Luckily, David Hood and his fellow musicians became more than just his friends but mentors.

Several years later, Jason Isbell joined the Drive-By Truckers on tour in support of their third studio album Southern Rock Opera (2001). He would later grab the golden chance to replace Rob Malone following his departure. Jason Isbell spent six years with Drive-By Truckers penning lyrics to some of the band’s songs. His then-wife Shonna Tucker joined the band too, playing the bass guitars. However, the two separated, with Jason Isbell later marrying The Highwomen founder Amanda Shires.

Jason Isbell embarked on a solo career, releasing his debut solo album Sirens of the Ditch in 2007. He later released two albums with The 400 Unit before releasing one of his most acclaimed albums Southeastern (2013). Southeastern (2013) had its unique sound as a blend of Americana and alternative country. The album rose to number twenty-three on the Billboard 200.

Southeastern (2013) is also home to “Cover Me Up,” one of the best Jason Isbell songs of all time. The album led Jason Isbell to win the Album of the Year, Artist of the Year, and Song of the Year awards in the 2014 Americana Music Honors & Awards ceremony. John Prine and Bruce Springsteen were among the reputable artists who lauded Jason Isbell for such an incredible album.

Jason Isbell got back to the studio to record and release his fifth studio album, Something More Than Free (2015). The album is home to several of the best Jason Isbell songs, including “Children of Children” and “24 Frames.” Something More Than Free (2015) won Jason Isbell his first Grammy Award for the Best Americana Album in 2016. He beat competition from albums by Emmylou Harris and Rodney Crowell, Brandi Carlile, The Mavericks, and Punch Brothers.

His song “24 Frames” won him a second Grammy Award in 2016 under the Best American Roots Song category. Jason Isbell has released three more albums, all of which he has featured The 400 Unit. One of the best albums of the three is The Nashville Sound (2017). The album topped the Billboard Folk Albums, Billboard Top Country Albums, Billboard Independent Albums, and Billboard Top Rock Albums. It also managed to rise to number four on the Billboard 200.

The Nashville Sound (2017) won the 2018 Grammy Award for the Best Americana Album. “If We Were Vampires” is one of Jason Isbell’s most popular hits from the album. The song won Jason Isbell his fourth Grammy Award under the Best American Roots Song category. Jason Isbell also bagged the UK Americana Awards accolade for the International Album of the Year, credit to The Nashville Sound (2017). Earlier in 2016, Jason Isbell had won the International Artist of the Year accolade on the UK Americana Awards.

#10 – Alabama Pines

Ushering us into the top 10 Jason Isbell songs is the hit “Alabama Pines.” The song is featured on Here We Rest (2011). “Alabama Pines” alludes to the cry of a guy holding on to the last of what is entitled to him. This soul-drifting track was named the Song of the Year at the 2012 Americana Music Honors & Awards ceremony. Jamey Johnson released a song under the same title (but with different lyrics) in 2015.

#9 – Relatively Easy

“Relatively Easy” is one of Jason Isbell’s musical gems from his album Southeastern (2013). The song finds the singer trying to remind its listeners that they should quit whining since there is always someone who has seen worse days. Nevertheless, he shows how much depression can be damaging to someone. Hence, the song serves as a warning to avoid drowning in depression by turning bitter days into days of perseverance and hope.

#8- Dreamsicle

Number eight on our top 10 Jason Isbell songs is “Dreamsicle.” The song is featured on Jason Isbell’s album Reunions (2020). “Dreamsicle” alludes to a sad narrative about a child almost getting caught up in the drama of a disintegrating family. Jason Isbell’s childhood inspires this melodic country ballad.

#7 – Children of Children

Once more, Jason Isbell hit the studio inspired by familial feelings to release his hit “Children of Children.” The song finds him singing about he and his wife broke what he felt to be like a cycle of getting kids at a young age in his family. Jason Isbell was born when his mother and father were just teenagers (seventeen and nineteen years old, respectively). In some way, starting a family at a young age might have fuelled the breakup between his parents.

#6 – Something More Than Free

Number six on our top 10 Jason Isbell songs is the hit “Something More Than Free.” The song is the album title track to Jason Isbell’s fifth studio album, released in 2015. “Something More Than Free” finds the singer telling of a narrative of a blue-collar worker. The worker tries to safeguard a better life for his family.

#5 – Hope the High Road

Jason Isbell released “Hope the High Road” as the lead single to his award-winning album The Nashville Sound (2017). The song finds Jason Isbell repudiating to be tormented into hopelessness. In this political song, the singer laments the divisive social climate and the dissatisfaction of many citizens of the US since the election of Trump as president.

#4- If We Were Vampires

Yet another great ballad from Jason Isbell’s album The Nashville Sound (2017) is “If We Were Vampires.” The song finds the singer telling of a bitter fact that death is a destination every soul must get to at the end. “If We Were Vampires” serves as a reminder to the human race that love might be forever, yet life is finite. His wife, Amanda Shires, provides backing harmony vocals to this sad yet realistic ode. The song won a Grammy Awards in 2018 in the Best American Roots Song category.

#3 – Elephant

One of the most popular heart-breaking masterpieces by Jason Isbell is the hit “Elephant.” The song is featured on his album Southeastern (2013). Its lyrics allude to a heart-rending narrative of a friend who is dying of cancer. The friend in the subject was a girl he was once dating. Patterson Hood of Drive-By Truckers lauded “Elephant” as his Song of the Year 2013.

#2 – 24 Frames

“24 Flames” is the best Jason Isbell song from his album Something More Than Free (2015). The song has been lauded as a tribute to Athens, Georgia. Athens was home to the Drive-By Truckers. “24 Frames” won a Grammy Award for the Best American Roots Song in 2016. It also won the Song of the Year award at the 2016 Americana Music Honors & Awards ceremony.

#1 – Cover Me Up

Number one on our top 10 Jason Isbell songs list is the hit “Cover Me Up.” The song is featured on Jason Isbell’s album Southeastern (2013). Surprisingly, his album Southeastern (2013) was just two days old after recording when the singer wed Amanda Shires. “Cover Me Up” is the opening track to the album. The song finds Jason Isbell asking Amanda to shield him with love. “Cover Me Up” won the Song of the Year award at the 2014 Americana Music Honors & Awards ceremony.