It stars Dylan alongside a star-heavy cast, including John Goodman, Jeff Bridges, Penélope Cruz, Val Kilmer, Mickey Rourke, Jessica Lange, Luke Wilson, Angela Bassett, Bruce Dern, Cheech Marin, Ed Harris, Chris Penn, Steven Bauer, Giovanni Ribisi, Michael Paul Chan, Christian Slater, and Fred Ward.

An iconic rock legend, Jack Fate (Bob Dylan), is bailed out of prison to perform a one-man benefit concert for a decaying future North American society.

The film touches on many subjects, from the futility of politics to the confusion of loosely strung government conspiracies, to the chaos created by both anarchy and Nineteen Eighty-Four-styled totalitarianism.

In the late 1990s, Dylan was allegedly inspired by the films of Jerry Lewis and decided he wanted to write and star in a slapstick television show for the HBO network.

[1] Larry Charles, who had written and produced for Seinfeld and Mad About You, was brought in to meet with the musician regarding the project at Dylan's boxing gym in Santa Monica.

[1] Charles decided to stay on as co-writer and director, with the concept of the project eventually evolving from a slapstick television show into the dramatic film Masked and Anonymous.

[3] Many of the film's actors worked for "scale" (union wages) for a chance to appear alongside Dylan, including Jeff Bridges, John Goodman (reunited after their work together in the 1998 Coen Brothers film The Big Lebowski, which also featured the 1970 Dylan song "The Man in Me"), Bruce Dern, Jessica Lange, Penélope Cruz, Luke Wilson, Cheech Marin, Ed Harris, Chris Penn, Giovanni Ribisi, Christian Slater, Mickey Rourke, and Angela Bassett.

[5] Chicago Sun-Times critic Roger Ebert gave the film a 1/2 star (out of a possible four) rating, and deemed it "a vanity production beyond all reason".

[6] A number of reviewers commented on Dylan's acting, writing that he appeared "near-catatonic" and that he stared "in mute incomprehension", "never speaking more than one line at a time" and only making remarks that "evoke the language and philosophy of Chinese fortune cookies".

[4] Amongst the positive reviewers was The Washington Post, stating that the film is a "fascinating, vexing, indulgent, visionary, pretentious, mesmerizing pop culture curio".

[13] Dylan was nominated for a Grammy Award for Best Male Rock Vocal Performance for his new rendition of "Down in the Flood" on the film's soundtrack.

"Knockin' on Heaven's Door" (a song Dylan first recorded for Pat Garrett and Billy The Kid ) was also filmed, but only a brief portion appears in the DVD's supplemental material.

Larry Charles mentions "All Along the Watchtower" (a song from John Wesley Harding) during his interview on the DVD – saying Dylan intended to play it until the last moment, then decided not to.