Charley Crockett stopped by The Daily Show to promote his new album, The Man From Waco Redux, on Tuesday. The Texas troubadour sat down for a candid interview with guest host Jordan Klepper and performed his song “Name on a Billboard”.

Crockett and his interviewer covered a lot of ground in their conversation, including his journey from busking in the New York City subway to opening for Willie Nelson just a stones throw from “the first bridge [he] played under” after hitchhiking to the city and finding a couch to crash on. He also talked about his collaboration with Bob Dylan on the song “Tom Turkey”, which will appear on the new album, and discussed their shared fascination with Billy the Kid, on whom the song is based.

The discussion deepens as Klepper, who says he’s “been a big fan for quite some time,” asks Crockett about his success and whether he sees it has a journey or a destination he’s already reached. Crockett responds by saying his former managers seem to think he had it all planned out from the start, but he doesn’t feel that way: “They all said [I] had this grand scheme, but I never did. This was a career of last resort. Hard luck and circumstance put me on street corners. I wouldn’t be in this business if I’d had an easy way.”

Watch the full interview and check out Charley Crockett’s performance of “Name on a Billboard” below.

The Man From Waco Redux is due out May 26th and will feature revamped version of five songs from the original The Man From Waco album.

Charley Crockett The Daily Show Interview

Charley Crockett – “Name On A Billboard” Live On The Daily Show