11. Bob Dylan: The Thirtieth Anniversary Tribute (1993)
Also known as Bobfest, this tribute concert was filmed at Madison Square Garden on October 16, 1992, featuring many Last Waltz alums like Eric Clapton and Neil Young, and starring additional new faces: Willie Nelson, Eddie Vedder, Stevie Wonder, Lou Reed, Johnny and June Carter Cash, etcetera. The climax? When Sinead O'Connor gets booed off the stage for publicly ripping apart a picture of the Pope two weeks earlier. Remember that one? Released on VHS in 1993, the film was out of print for over a decade until NTSC finally released the DVD edition in March 2009. But beware, this new DVD edition is a horribly truncated import of dubious quality, and with the songs out of order to boot.
This film is Dylan's tragicomic take on endtimes. In his cinematic masterwork directed by Larry Charles, co-writer Dylan plays rock icon Jack Fate, who prophetically examines the futuristic far west—a ruined wasteland of decadence and cold totalitarianism. In a roster that makes The Thin Red Line cast look like the lineup for a one-act play, the film stars a score of A-list actors, like John Goodman, Jeff Bridges, Penelope Cruz, Ed Harris, Bruce Dern, etc. (everyone wanted in on Dylan's film, naturally). Despite its mixed reception, this film will stand forever as an underground classic, the testament of a savage eye bent on challenging the consumer culture to question itself, its motives, and its mores.
13. Dylan's Victoria's Secret Ad (2004)
Here's another one of those Dylan controversies that's just as talked-about today as it was after its 2004 airing. Dylan not only gave Victoria's Secret permission to use one of his songs for a skimpy lingerie ad, but he also starred in it. In this noirish 30-second sketch backed by Time Out of Mind's “Lovesick,” Dylan is presented as the aging, goateed, Stetson-wearing man in a long black coat who steels his lusty desires for the vestal charms of a lingerie-clad angel seductress with sky-gray eyes. After watching this artfully classy clip, it's hard to find any toehold for criticism, and you're forced to ask yourself, "Well, wouldn't you?"
Martin Scorcese once said, "Cinema is a matter of what's in the frame and what's out." What's in the frame in this masterful four-hour documentary is the chronological life of Bob Dylan from childhood until his 1966 creative peak. Seeing that sales cliche "the definitive," alongside Bob Dylan's name is almost laughable. But No Direction Home is indeed the definitive Bob Dylan documentary. Captivating archaic footage tossed up with candid Dylan interviews create an intimate, three-dimensional portrait of this larger-than-life songwriter and American cultural icon. A must-see film for Dylan fans of any stripe.
Murray Lerner's documentary chronicles all three of Dylan's Newport performances, including the controversial 1965 malaise when the pioneering folk legend shifted gears into electric. This brilliant time capsule documentary captures Americana unfolding as '60s experimentalism eclipses the staid sentiments of the fading '50s.
Based on his book The People's History of the United States, this impassioned television special ended up becoming the swan song of famed and controversial historian Howard Zinn. On stage, actors Viggo Mortensen, Marisa Tomei, Matt Damon, Morgan Freeman and others read historical documents and poetry in what Zinn described as a clarion call for activism. The music segment features Eddie Vedder performing Bob Dylan's “Masters of War,” while Dylan does a rough hewn but exceptionally crisp rendition of Woody Guthrie's “Do Re Mi.”