I don’t know if anything specific on the date or circumstances of this photo has ever come to light, but there’s a quote in Robert Shelton’s “No Direction Home: The Life And Music of Bob Dylan” which apparently describes this shot and seems to place it as circa 1956-1957. During the spring of 1968, when Shelton was in Hibbing interviewing Abe and Beatty Zimmerman, he was given a tour around the home and was shown albums containing family photos. Abe Zimmerman remarked, “Bobby was fifteen when he posed with a cowboy hat on and a cigarette dangling out of his mouth. I sent the picture to him a while ago with his photo from the ad for Dont Look Back. It had exactly the same expression.”