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The 25 Best Jason Isbell Songs, from Cover Me Up to If We Were Vampires

Jason Isbell is one of the finest songwriters in American music, an Alabama storyteller whose songs about love, loss, sobriety and the South have won six Grammys. Here are his 25 best songs, album by album, from his Drive-By Truckers classics to Southeastern, Something More Than Free, The Nashville Sound and Weathervanes, with the stories behind Cover Me Up and If We Were Vampires.

What is Jason Isbell's most famous song?

"Cover Me Up" is Jason Isbell's most famous song, a 2013 love song from Southeastern that won Americana Song of the Year and has been covered by Morgan Wallen and many others. "If We Were Vampires", "24 Frames" and "Cast Iron Skillet" each won the Grammy for Best American Roots Song, and "Elephant" and "Alabama Pines" are fan favorites.

Jason Isbell's essential songs

  1. "Cover Me Up", 2013: a raw, devoted love song written about getting sober and falling in love.
  2. "If We Were Vampires", 2017: a Grammy-winning love song about making the most of the time you have.
  3. "Elephant", 2013: a devastating song about a friend facing cancer.
  4. "24 Frames", 2015: a Grammy-winning song from Something More Than Free.
  5. "Alabama Pines", 2011: a homesick song that won Americana Song of the Year.
  6. "Cast Iron Skillet", 2023: a Grammy-winning story song from Weathervanes.
  7. "Something More Than Free", 2015: the title track, about working hard for the people you love.
  8. "Dreamsicle", 2020: a nostalgic song about childhood, from Reunions.
  9. "King of Oklahoma", 2023: a Grammy-nominated story song from Weathervanes.
  10. "Decoration Day", 2003: his Drive-By Truckers song about a real family feud.

Drive-By Truckers songs

  1. "Outfit", 2003: a father's advice to his son, one of his most loved songs.
  2. "Never Gonna Change", 2004: a defiant Southern rocker from The Dirty South.
  3. "Danko/Manuel", 2004: a tribute to members of The Band.

Songs from Southeastern (2013)

Southeastern, his first album after getting sober, is widely considered his masterpiece and one of the best Americana albums ever made.

  1. "Traveling Alone", 2013: a song about the loneliness of life on the road.
  2. "Stockholm", 2013: a gentle song about missing someone far away.
  3. "Songs That She Sang in the Shower", 2013: a quiet song about regret.
  4. "Live Oak", 2013: a haunting story song.

Songs from The Nashville Sound (2017) and Reunions (2020)

  1. "Last of My Kind", 2017: the album's opening song about feeling left behind.
  2. "White Man's World", 2017: a thoughtful song about privilege.
  3. "Hope the High Road", 2017: a hopeful rocker.
  4. "Anxiety", 2017: a sprawling song about living with anxiety.
  5. "What've I Done to Help", 2020: the opener of Reunions.
  6. "Only Children", 2020: a tender song about a friend from childhood.

More songs

  1. "Maybe It's Time", 2018: written by Isbell and sung by Bradley Cooper in A Star Is Born.
  2. "Foxes in the Snow", 2025: the Grammy-nominated title song of his 2025 solo album.

Who is Jason Isbell?

Jason Isbell was born on February 1, 1979, in Green Hill, Alabama, near Muscle Shoals, and grew up playing music with his family. He joined the Drive-By Truckers in 2001 and wrote some of their best songs, including "Outfit" and "Decoration Day", before leaving in 2007 to go solo. His records with his band, the 400 Unit, and on his own have made him one of the most respected songwriters in country and Americana music, and he has won six Grammys.

Sobriety and Southeastern

In 2012, after years of heavy drinking, Isbell entered a rehab program in Nashville after an intervention by Amanda Shires, his manager and his friend Ryan Adams. Southeastern, released the following year, was the first album he made sober. Its songs, from "Cover Me Up" to "Elephant", are clear-eyed and unflinching, and they made him a star. He and Shires married in 2013 and had a daughter before divorcing in 2025.

The story behind Cover Me Up

"Cover Me Up" is a love song about the moment someone helps you climb out of the hardest time in your life, written as Isbell was getting sober. Its quiet guitar and huge, aching vocal made it his best-known song, and it won Americana Song of the Year in 2014. Morgan Wallen's 2021 cover introduced it to millions of new listeners, and it has become a favorite for weddings and anniversaries.

The story behind If We Were Vampires

"If We Were Vampires", from The Nashville Sound, is a love song about how the shortness of life makes every ordinary day together more precious. It won the Grammy for Best American Roots Song in 2018, and it is often chosen for weddings and anniversary dedications.

Grammy wins

Isbell won Best American Roots Song and Best Americana Album together three times: for "24 Frames" and Something More Than Free in 2016, "If We Were Vampires" and The Nashville Sound in 2018, and "Cast Iron Skillet" and Weathervanes in 2024. He also appeared as an actor in Martin Scorsese's Killers of the Flower Moon in 2023.

The 400 Unit and the Ryman

Isbell's band, the 400 Unit, takes its name from the psychiatric ward of a hospital in Florence, Alabama, near where he grew up. The group, including bassist Jimbo Hart, drummer Chad Gamble, keyboardist Derry deBorja and guitarist Sadler Vaden, has played on most of his records since 2009. Each year Isbell plays a multi-night residency at Nashville's Ryman Auditorium, and the live albums Live from the Ryman (2018) and Live from the Ryman Vol. 2 (2024) capture how his songs grow on stage.

Foxes in the Snow

In March 2025 Isbell released Foxes in the Snow, a quiet, solo acoustic album made with just his voice and guitar. Its songs are some of the most personal he has written, and the album and its title song earned him Grammy nominations, including Best Folk Album. For fans of his early, stripped-down songs, it is a perfect place to start.

Jason Isbell albums to start with

  • Southeastern (2013): his masterpiece, with "Cover Me Up" and "Elephant".
  • Something More Than Free (2015): Grammy-winning, with "24 Frames".
  • The Nashville Sound (2017): with "If We Were Vampires".
  • Reunions (2020): with "Dreamsicle".
  • Weathervanes (2023): with "Cast Iron Skillet" and "King of Oklahoma".

Jason Isbell songs for a wedding or an anniversary

"Cover Me Up" and "If We Were Vampires" are the favorites for a first dance or an anniversary dedication, and "Stockholm" is a gentle alternative. "Something More Than Free" makes a meaningful dedication to a hardworking spouse on a milestone anniversary. For more, see our country wedding songs and anniversary songs.

Jason Isbell songs for a hard time or a memorial

"Elephant" speaks to anyone watching a friend face a serious illness, and "Outfit" and "Alabama Pines" are moving at a memorial for someone from the South who never forgot where they came from. If someone you love is struggling with drinking, see our songs about addiction, which lists where to find help.

More great songwriters

If you love Jason Isbell, try our Noah Kahan songs, Whiskey Myers songs and Kris Kristofferson songs.

A song as personal as Cover Me Up

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Everything you want to know

What is Jason Isbell's most famous song?

"Cover Me Up" is Jason Isbell's most famous song. "If We Were Vampires", "Elephant", "24 Frames" and "Alabama Pines" are his other best-known songs.

How many Grammys has Jason Isbell won?

Jason Isbell has won six Grammys: Best American Roots Song for "24 Frames", "If We Were Vampires" and "Cast Iron Skillet", and Best Americana Album for Something More Than Free, The Nashville Sound and Weathervanes.

Was Jason Isbell in the Drive-By Truckers?

Yes. Jason Isbell was a member of the Drive-By Truckers from 2001 to 2007 and wrote songs like "Outfit" and "Decoration Day" before starting his solo career.

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