[1] His career began as a guitarist for Emmylou Harris' Nash Ramblers with whom he won his first Grammy for their Live at the Ryman album in 1992.

As a songwriter, Randall has had many notable cuts including "Whiskey Lullaby" recorded by Brad Paisley and Alison Krauss which won the 2005 CMA Song of the Year Award,[3] and “Tin Man” by Miranda Lambert which won the 2018 ACM Song of the Year Award.

[4] He has also had cuts with Reba McEntire, Emmylou Harris, Maren Morris, Dierks Bentley, Kenny Chesney, Kip Moore, Brad Paisley, Scotty McCreery, Guy Clark, Little Big Town, Gary Allan and Travis Denning.

[7][8][9][10] Randall's production on The Mountain's "Burning Man ft. Brothers Osborne" also earned him the 2019 ACM Award for Music Event of the Year.

[10] Other artists he has produced records for include: Dwight Yoakam, Jack Ingram, Pat Green, Nitty Gritty Dirt Band, Jessi Alexander, and Parker McCollum.

[2][15] Between 1995 and 2005 Randall released four solo albums, What You Don't Know, Cold Coffee Morning, Willin' and Walking Among the Living.

The singles "Cold Coffee Morning" and "This Heart" both made appearances on the Billboard Hot Country Songs Charts.

[20] Randall is also a member of 18 South, a culmination of acclaimed songwriters and Nashville's best session musicians consisting of Jessi Alexander, Jimmy Wallace, Mike Bub, Larry Atamanuik and Guthrie Trapp.

[22] Randall co-wrote the song "Whiskey Lullaby" with Bill Anderson, which was released by Brad Paisley as a duet with Alison Krauss in 2004.

[7][8] Their production on The Mountain's "Burning Man ft. Brothers Osborne" also earned them the 2019 ACM Award for Music Event of the Year.

[34][35] In 2020, Randall produced Parker McCollum’s EP Hollywood Gold, with the lead single "Pretty Heart" achieving platinum certification.

He has produced for artists including Dierks Bentley, Dwight Yoakam, Pat Green, Nitty Gritty Dirt Band, Jessi Alexander, and Parker McCollum.

His extensive list of cuts also includes Miranda Lambert, Reba McEntire, Emmylou Harris, Maren Morris, Dierks Bentley, Kenny Chesney, Kip Moore, Brad Paisley, Scotty McCreery, Guy Clark, Little Big Town, Gary Allan and Travis Denning.