On June 16, 2017, Earle & the Dukes released his seventeenth studio album, So You Wannabe An Outlaw. GUY, Earle's tribute album to his songwriting hero Guy Clark was released on March 29, 2019.
Earle is outspoken with his political views, and often addresses them in his lyrics and in interviews. Politically he identifies as a socialist, but tends to vote for Democratic candidates, despite not agreeing entirely with their politics. During the 2016 election, he expressed support for Senator Bernie Sanders, whom he considered to have pushed Hillary Clinton to the left on important issues. In a 2017 interview Earle stated about President Donald Trump: "We’ve never had an orangutan in the White House before. There’s a lot of “What does this button do?” going on. It’s scary. He really is a fascist. Whether he intended to be or not, he’s a real live fascist." However, Earle has called for the American left to engage with the concerns of working class Trump voters, saying in 2017: "…maybe that’s one of the things we need to examine from my side because we’re responsible. The left has lost touch with American people, and it’s time to discuss that". In 2020, he stated: "I thought that, given the way things are now, it was maybe my responsibility to make a record that spoke to and for people who didn’t vote the way that I did. One of the dangers that we’re in is if people like me keep thinking that everyone who voted for Trump is a racist or an asshole, then we’re fucked, because it’s simply not true."