Its plot could be called thin on a superficial level; an iconic rock legend, Jack Fate, is bailed out of prison to perform a one-man for a decaying future North American society. Yet this is only a starting point for the deeper philosophical questions raised beneath the film's strange, meandering story. The film touches on many subjects from the futility of politics, the confusion of loosely strung government conspiracies, and the chaos created by both and -styled .
It further reflects on , (with some scenes being reminiscent of the film " "), and 's place in a seemingly increasingly chaotic world.
In some ways, the film is political: it describes how Fate sees the political landscape (people fighting for no reason, a nation without hope, governments that can not be trusted) but at the same time Fate makes it clear that he "was always a singer and maybe no more than that". He produces no solutions to any of the problems the film presents.
Rather, he makes it clear that he "stopped trying to figure everything out a long time ago."
The film was shot in only twenty days and was funded by the . It was distributed by , a well-known distributor of independent productions.
The soundtrack is composed almost entirely of covers of Bob Dylan songs ranging from his very early 1960s-era material to work as recent as songs from his -award winning album " ". Artists who perform the songs include , , and .
Many of the film's actors worked for "scale" (union wages) for a chance to appear alongside Dylan, including , (reunited after their work together in the film , which also featured the Dylan song " "), , (who has had a long time relationship with playwright who co-wrote the composition " " with Dylan, from the album " "), , , , , , , , , and .
In addition to several other actors of note, the band of the lead character is played by Dylan's actual touring band of the time. Other stars in the include and .
Music from Dylan's entire career is presented in the movie, though his recent album Time Out Of Mind receives considerable play, with "Dirt Road Blues" and "Not Dark Yet" both used as background in scenes; Dylan also plays a new arrangement of "Cold Irons Bound" in the film's climax.
Furthermore, a live performance of "Standing in the Doorway" was cut from the final edit, but included as a bonus on the DVD.
From 1999 to 2002, Dylan's touring band was joined by veteran guitarist Charlie Sexton. Already an accomplished unit, the band's new configuration was arguably Dylan's best touring group since 1974, when Dylan played a brief two-month American tour with .
Highlighted by the interplay of Sexton and guitarist Larry Campbell, the group also featured Dylan's longtime bassist , as well as two drummers: David Kemper (who left the band in late 2001) and George Receli (who was Kemper's replacement). Dylan began filming Masked Anonymous soon after Receli's arrival.
Masked Anonymous marked the first (and to date, only) release of "live" material from this unit.
According to director Larry Charles, who recorded an interview for the film's DVD release, 20 or more songs were recorded for the film, with Charles telling Dylan he could play anything he wanted.
For the most part, the songs were recorded at Stage 6, Ray-Art Studios, , on July 18, 2002. Though all were presumably filmed, only a handful were used.
The following songs were featured in the film, with unedited versions included in the soundtrack release: "Down In The Flood" (a song from ), "Dixie" (traditional), "Diamond Joe" (traditional), and "Cold Irons Bound" (a song from Time Out Of Mind).
The following songs were used for the film, but were never issued on CD: "Drifter's Escape" (a song from ), "I'll Remember You" (a song from ), "Blowin' in the Wind" (from ), "Watching The River Flow" (a song dating from 1971, when it was released as a single), "Dirt Road Blues" (from Time Out Of Mind) and " " (traditional). Of these songs, only "I'll Remember You" was featured unedited and uninterrupted in the film.
As mentioned, "Standing In The Doorway" (another song from Time Out Of Mind) was featured as an alternate scene on the DVD. Unfortunately, it's interrupted by a few cut-aways to other characters in the film.
"Knockin' on Heaven's Door" (a song Dylan first recorded for ) was also filmed, but only a brief portion appears in the DVD's supplemental material.
A new 'fiddle' arrangement of "If You See Her, Say Hello" (from ) was also filmed, but it only appears as background music during the DVD's supplemental material.
Larry Charles mentions "All Along the Watchtower" (a song from John Wesley Harding) during his interview on the DVD, but no portion has ever been released.
As mentioned, a new recording of "Blowin' in the Wind" was used for the film.
This is heard over the film's final shots and end credits. Unlike the other performances used in the film, this was a concert performance recorded at Santa Cruz Civic Auditorium, , on March 16, 2000 (when David Kemper was still with the band). This performance was previously found on the limited edition bonus CD single given away with The Best Of Bob Dylan Vol.
2 in the United Kingdom, and it was also featured on a promo CD single Live Rare 2. Approximately 45 seconds of the harmonica solo was cut for the film while the previous CD releases feature the performance unedited.
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