Rawlings attended the Berklee College of Music and studied with Lauren Passarelli. He produced albums by Gillian Welch, Willie Watson and Old Crow Medicine Show. He leads the Dave Rawlings Machine with Gillian Welch, Willie Watson, Paul Kowert, and Brittany Haas. John Paul Jones of Led Zeppelin has been known to play mandolin with the band occasionally. He 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". He vocal style has often been compared to that of Bob Dylan.
The Dave Rawlings Machine album A Friend of a Friend was released on November 17, 2009. Rawlings recorded the album in Nashville, and produced it himself. 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. The album features a medley of a Neil Young and Bright Eyes songs, as well as songs Rawlings co-wrote with Ryan Adams and Old Crow Medicine Show.
In 2015 Dave Rawlings Machine released a second album, Nashville Obsolete. The album was named to Rolling Stone's list of the top 40 country albums of 2016. 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.
Poor David's Almanack, released on August 11, 2017 via Acony Records, is the eighth collaborative LP for Rawlings and Welch and the first under the name David Rawlings. In addition to Welch and Watson, the backup band includes Ketch Secor of Old Crow Medicine Show, and Taylor and Griffin Goldsmith of Dawes. The album was recorded with Ken Scott and Matt Andrews at the Rawlings/Welch duo's Woodland Sound Studios in Nashville. The album features an original woodcut piece by Gillian Welch on the cover and was notably the first vinyl release on Welch and Rawlings' Acony record label.
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.— Brittney McKenna, Rolling Stone
Rawlings achieves his signature guitar sound flatpicking a small archtop guitar. The 1935 Epiphone Olympic that has been his primary instrument was a mid-priced guitar for its time, with a carved arched solid sprucewood top, carved arched solid mahogany back and mahogany sides. It sold for about $35 in 1935. The guitar's lower bout measures 13 5/8 inches wide, and it has three piece f-holes.
Rawlings "scavenged" the guitar from a friend's attic and is now hardly seen playing anything else. As he states, "I just picked it up. It was filthy, and it didn't have strings. You could just see the shape of it under the sawdust." Rawlings tuned it and brought it to a recording session for the Welch's first record. "As soon as I heard it through the microphone and through the speakers I was like, 'I love this guitar.'" he says.
With Ryan Adams
With Bright Eyes