Sturgill Simpson recorded this bluegrass album during the COVID-19 pandemic in 2020 at the Butcher Shoppe studio in Nashville. The album reinterprets songs from his previous catalog, including tracks from High Top Mountain, Metamodern Sounds in Country Music, and A Sailor's Guide to Earth.
Simpson assembled top session musicians, including Stuart Duncan, Sierra Hull, and Tim O'Brien, to create a traditional bluegrass sound with his signature style. The album was released on October 16, 2020, under the Thirty Tigers label.
The title references Simpson's nickname 'Cuttin' Grass' and the studio where it was recorded. The project was a critical and commercial success, reaching number one on the Billboard Bluegrass Albums chart.