- From Jackson, Kentucky; grew up in Lexington. Lives in Nashville.
- 2004, after serving in the U.S. Navy, he formed a country-rock band in Seattle, Washington called Sunday Valley.
- 2012, moved to Nashville and recorded his first album High Top Mountain (no label).
- 2014, released Metamodern Sounds of Country Music (High Top Mountain Music). Made guest appearances on Late Night with David Letterman, The Tonight Show with Jimmy Fallon, The Conan O’Brien Show and several other late night programs.
- 2015, toured with Willie Nelson and Merle Haggard.
- 2016, released A Sailor’s Guide to Earth album (Atlantic).
- 2018, he acted in the movie Orca Park. Since then, he has acted in several other films.
- 2019, released Sound and Fury album (Elektra).
- 2020, released two bluegrass albums, Cuttin’ Grass Volume 1 and Cuttin’ Grass Volume 2 (High Top Mountain).
- 2021, released a third bluegrass album, The Ballad of Dood and Juanita (High Top Mountain).