Sturgill Simpson

The budding singer/songwriter relocated to Music City in the early aughts, but he couldn't figure out how to break into the scene there. Instead, he retreated to a full-time job working for Union Pacific Railroad and playing music on the side.

But music was never meant to be Simpson's hobby. In 2012, he tried Nashville once again, this time raising money to record his debut album, 2013's High Top Mountain. It was produced by Dave Cobb and showed off Simpson's low country twang and traditional approach to the genre.

He worked with Cobb once again on 2014's Metamodern Sounds in Country Music, an album that quickly began garnering critical attention for the way it took traditional country and updated the stories it told. Simpson earned a Grammy nomination for Best Americana Album.

Yet, it would take one more release for Simpson to win a Grammy. His third album, 2016's A Sailor's Guide to Earth, won the award for Best Country Album and was nominated for Album of the Year. The album, written to Simpson's young son, is a guide of sorts about the best way to live and was recorded live with Simpson taking over producing duties from Cobb.

With three critically successfully country albums under his belt, Simpson began switching it up. 2018's Sound & Fury drew more on rock 'n' roll, while 2020's double album Cuttin' Grass, Vol. 1 and Vol. 2 explored the bluegrass genre. In 2021, Simpson released the narrative-heavy album The Ballad of Dood and Juanita.

Beyond playing music, Simpson has a growing film career. Besides contributing the title song to Jim Jarmusch's indie zombie film The Dead Don't Die, Simpson also appears in the film. He also played a police officer in Queen & Slim, and is set to appear in Martin Scorsese's film Killers of the Flower Moon.