“Don’t Think Twice, It’s Alright” was written by Bob Dylan and released on his second album, The Freewheelin’ Bob Dylan, in May 1963. The song is widely understood to be rooted in Dylan’s early-1960s relationship with Suze Rotolo — her extended absence in Italy is the gap the song works through. The melody borrows from Paul Clayton’s arrangement of an older traditional piece (“Who’s Gonna Buy Your Chickens When I’m Gone” / “Who’s Gonna Buy You Ribbons”), a debt Dylan has acknowledged at various times.
The song became one of the central pieces of the early-1960s folk revival almost immediately. Peter, Paul and Mary’s 1963 cover charted at No. 9 on the Billboard Hot 100 and gave the song a much wider audience than Dylan’s own recording reached at the time. Its conversational fingerstyle guitar pattern in the Travis-picking family became a teaching staple for an entire generation of acoustic guitarists.
The bluegrass life of the piece begins seriously with Lester Flatt and Earl Scruggs’s 1968 Columbia album Changin’ Times, which controversially set the Foggy Mountain Boys to working through Dylan and other contemporary songwriters. The choice contributed to the duo’s split a year later but it also planted Dylan firmly in the bluegrass repertoire; the song remains a comfortable singer’s piece and a frequent jam call. Lyrically it is a dignified, exit-without-bitterness farewell that has worn unusually well across covers.