The verses are illustrated using photographs of historical figures such as Adolf Hitler, Ronald Reagan, Muhammad Ali and Dylan himself, and paintings by artists such as Hieronymus Bosch, Francisco Goya, and Albrecht Dürer.

[8] In addition to Dylan, the song features Mark Knopfler and Mick Taylor on guitar, Alan Clark on the keyboard, Robbie Shakespeare on bass and Sly Dunbar on drums.

In its contemporary review of the single, Cash Box said that the reggae rhythm section provides "an infectious, bubbling bottom while [the guitarists] trade rough and sweet licks across the moving Dylan lyric" and that "at his stirring, thought provoking best on this one, Dylan summons the passion and fervor synonymous with his earlier work and delivers an inspiring vocal performance".

[17] As a guest writer for Rolling Stone, Chris Martin of Coldplay wrote a tribute to "Jokerman", writing "How can this guy [Dylan] have a song that comes from this other world, and it's still so brilliant?

[18] Rapper Wyclef Jean referred to the song in an interview as "the most incredible piece of literature I ever read" and a point of entry for him into the music of Bob Dylan.

Pure Bathing Culture's Daniel Hindman selected it, noting how "the lyrics of 'Jokerman' are these quips of mystic wisdom from a source only Bob is in touch with.

[24] Dylan's first live performance of the song, in which he was backed by guitarist J.J. Holiday and the rhythm section from the L.A.-based punk band The Plugz, took place on Late Night with David Letterman, on March 22, 1984.

[25][4] Ian Maxton, writing from the vantage point of 2020, called it "a blistering, righteous version of the song that ranks among his best-ever live performances.