In the late '70s/early '80s, Bob Dylan was spending a good time at a house and a boat he owned in the Caribbean, soaking up some of the local culture, and it is evident on the 1983 LP Infidels. Enlisting reggae über-rhythm section Sly (Dunbar) and Robbie (Shakespeare), much of the record continues the island-spiced rhythmic and melodic flavor of Shot of Love from 1981. "Jokerman" is not quite straight reggae, but it certainly spotlights Sly and Robbie's reggae-hewn grooves. The song is structured like a Caribbean folk song.
Dylan was also undoubtedly attracted to the spiritual quality of reggae -- whose top figures Bob Marley and Peter Tosh were both highly influenced by Dylan himself -- and Rastafarianism's particular amalgam of Judaism and Christianity. The songwriter had spent a good part of his recording career in the 1970s devoting himself to exploring Christianity and with Infidels, often mistakenly cited as a return to secularism, he seemed to find a path that allowed him to embrace two religious philosophies, now citing lines from both the New and Old Testaments: "Well, the Book of Leviticus and Deuteronomy/The law of the jungle and the sea are your only teachers." The song is rich with biblical allusions and references to both Judaism and Christianity -- including the stories of Jacob, who fooled his father with a layer of goat skin ("Shedding off one more layer of skin/Keeping one step ahead of the persecutor within") and Sodom and Gomorrah -- Dylan's narrator trying to make sense of all of the lessons from both religions. Indeed, the listener is left with the impression that both the narrator and the jokerman he addresses are Dylan himself trying to reconcile his roots and his newer religious explorations ("Freedom just around the corner for you").
Much of Infidels is dedicated to various points of view and life philosophies. We are presented with an assortment of narrators, some of whom are distrustful, and we are left to our own devices to try and make sense of it all and find the truth. The subject "Jokerman" is a messiah figure, if not Christ himself, the singer seemingly trying to determine if he is or is not a false prophet: "You were born with a snake in both of your fists/While a hurricane was blowing/Freedom just around the corner for you/But with the truth so far off, what good will it do?" Further evidence points to the jokerman as Dylan, who perhaps sees himself as a false prophet: "You're a man of the mountains, you can walk on the clouds/Manipulator of crowds, you're a dream twister." The verses vacillate between biblical scripture and the 20th century, between the personal and the mythical (and personal myths), with the subject in the end left at a loss, just a jokerman indeed: "Oh, Jokerman, you know what he wants/Oh, Jokerman, you don't show any response."