His father, Steve Earle, named him in honor of his own mentor, singer and songwriter Townes Van Zandt.

[3] Earle dropped out of school, occasionally touring with and working for his father, eventually moving to eastern Tennessee with other songwriters.

[6] From 2014 to 2017, Earle released a "family trilogy" of albums, comprising Single Mothers (2014), Absent Fathers (2015), and Kids in the Street (2017).

[8][9] In 2009, Earle co-billed The Big Surprise Tour with Gillian Welch and David Rawlings, Old Crow Medicine Show, and The Felice Brothers.

[12] In 2011, Earle received the Americana Music Award in the Song of the Year category for "Harlem River Blues".

[13] His album of the same name has been described as having a "gently flowing, urban Americana sound, with horns, organ and tangy electric guitar".

Performers included Steve Earle & The Dukes and special guests: Shooter Jennings, Bonnie Whitmore, Amanda Shires, Willy and Cody Braun, Buddy Miller, Ben Nichols (Lucero), Dustin Welch, Elizabeth Cook, Emmylou Harris, Jason Isbell, Jessica Lea Mayfield, Joe Pug, Jon Langford, Lilly Hiatt, Scotty Melton, Stacey Earle and Mark Stuart.