In 2020, Welch and Rawlings released All the Good Times (Are Past & Gone), which won the 2021 Grammy Award for Best Folk Album.

[5] Rawlings contributed to the albums Cassadaga by Bright Eyes, Spooked by Robyn Hitchcock, and Heartbreaker by Ryan Adams, with whom he wrote two songs, "To Be Young (Is to Be Sad, Is to Be High)" and "Touch, Feel and Lose".

Gillian Welch is credited as a co-writer on five of the album's songs as well playing in the band with members of Tom Petty and the Heartbreakers, Old Crow Medicine Show, and Bright Eyes.

[5] In late 2016 Acony issued Boots No 1: The Official Revival Bootleg, a deluxe version of the 1996 Welch album considered a "modern Americana classic" and the first collaboration for the duo.

[13][14] In addition to Welch and Watson, the backup band includes Brittany Haas, Paul Kowert, Ketch Secor of Old Crow Medicine Show, and Taylor and Griffin Goldsmith of Dawes.

[16][17] Start to finish, the album is a testament both to his immeasurable talent and to his essential place in the roots and Americana music scene.

It's also a chance for a guy otherwise happy to play sideman or stand behind the boards to step out just a touch further into a well-deserved spotlight.

In July 2020, Rawlings and Welch announced All the Good Times (Are Past & Gone), an album of covers and traditional songs recorded at their home during the COVID-19 lockdowns of 2020.