In 2009 Earle co-billed The Big Surprise Tour with Gillian Welch and David Rawlings, Old Crow Medicine Show, and The Felice Brothers. In 2012 he appeared in an episode of the HBO television series Treme with his father.
In September 2009, Earle received an Americana Music Award for New and Emerging Artist of the Year. In 2011 Earle received the Americana Music Award in the Song of the Year category for "Harlem River Blues". His album of the same name has been described as having a "gently flowing, urban Americana sound, with horns, organ and tangy electric guitar". That year he also contributed a cover of Maybe Baby on the 2011 tribute album Rave on Buddy Holly. and played Newport Folk Festival and the Hardly Strictly Bluegrass Festival.
Earle moved to New York City in 2009, then returned to Nashville for several years. He married Jenn Marie Maynard in 2013 and he and his wife lived on the West Coast. Their only child, a daughter named Etta, was born in June 2017.