With seven albums and a lengthy list of accolades to his name, Sturgill Simpson has proven himself as one of modern country music's most talented songwriters and performers. The Kentucky native kicked off his career by forming the band Sunday Valley in 2004, but the project eventually fizzled out. After moving to Nashville, Simpson spent years trying to make a name for himself as an artist while doing odd jobs and local gigs to pay the bills.

In 2013, he released he debut solo album High Top Mountain, which was produced by Dave Cobb and featured an impressive list of accompanying musicians, including accomplished session player Hargus "Pig" Robbins and pedal steel virtuoso Robby Turner, who previously performed with Waylon Jennings, Loretta Lynn, Bob Dylan and many more. The self-funded project didn't become an immediate hit, the critical buzz earned from the release helped build momentum toward the album that broke his career.

The 2014 release of his second Cobb-prodcued record, Metamodern Sounds in Country Music, skyrocketed Simpson from a relative unknown to a headlining act. He shared the stage with legends like Willie Nelson and Merle Haggard, and became the face of a new generation of country music traditionalists offering up an alternative to mainstream country's heavily pop and R&B-influenced sound.

Simpson's follow up record, A Sailor's Guide to Earth, 2019's rock-influenced album and accompanying anime film Sound & Fury, 2020's back-to-back bluegrass records Cuttin' Grass Vol. 1 and Vol. 2, and his 2021 traditional country concert album The Ballad of Dood and Juanita have proven Simpson's versatility and fearless attitude toward musical experimentation.

It should be no surprise that an artist as multi-talented as Simpson has forged lasting friendships and creative ties with some of music's biggest names. Let's take a look at 5 incredible Sturgill Simpson collaborations that every country fan should hear:

  • "Juanita"

    with Willie Nelson

    You won't hear Willie Nelson's voice on "Juanita," but his signature guitar solo is at the heart of this engaging story-song. The track is a cut from Simpson's celebrated 2021 concept album The Ballad of Dood and Juanita, which uses traditional country and bluegrass musicality to help tell the story of the fictional characters as they roam Simpson's home state of Kentucky.

  • "Resentment"

    with Kesha, Brian Wilson & Wrabel

    Released as the third single from pop singer-songwriter Kesha's 2020 record High Road, "Resentment" is a powerful country-leaning ballad that tackles the deep, complicated emotions that spawn out of a relationship overflowing with toxicity. Kesha recruited Simpson, The Beach Boys' Brian Wilson and fellow singer-songwriter Wrabel to create the tune, which showed off a new and evolved sound for the star.

  • "Ain't Livin' Long Like This"

    with Margo Price

    Fellow country talent and longtime friend Margo Price welcomed Sturgill Simpson as a surprise guest during her 2018 headlining show at Nashville's Ryman Auditorium. The pair shared a few songs together, including this rollicking cover of "Ain't Livin' Long Like This," which was written by Rodney Crowell and brought to No. 1 on country radio by Waylon Jennings in 1979. The collaboration was recorded and released as a track on Price's 2020 live album Perfectly Imperfect at The Ryman.

  • "Summer's End"

    with John Prine and Brandi Carlile

    The late, great John Prine invited Simpson and Brandi Carlile to share the stage for a 2018 appearance on The Late Show with Stephen Colbert. The performance of "Summer's End," the poignant track from Prine's eighteenth and final album The Tree of Forgiveness, supplies a simple but stunning television moment that won't soon be forgotten.

  • "Midnight Train to Memphis"

    with Chris Stapleton

    Written by Stapleton and his former SteelDrivers bandmate Mike Henderson, "Midnight Train to Memphis" is a longtime staple of the country star's live show and a cut from his acclaimed 2017 record, From a Room: Volume 2. When it came time for Stapleton to make his Saturday Night Live debut in 2018, he recruited Simpson to play guitar alongside him. The result is an electric, engaging performance that shows off both artists' inarguable star power.