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The Most Iconic Bob Dylan Moments in Film

Bob Dylan is back in the news. The 79-year-old music legend recently sold his entire catalog of work to Universal in a record-breaking deal that reportedly cost over $300 million and included over 600 songs.

Even that much might even feel a bit low when considering the unparalleled impact Dylan has had on pop culture over the past 60 years; the Minnesota native rose in the midst of a changing nation in the 1960s and became the unexpected face of a movement.

Dylan’s work has informed, inspired and become part of the culture throughout his career to the point that he’s almost taken for granted as an American institution.

Dylan’s scheduled 2020 tour may have been canceled by COVID-19, but he’s not showing any signs of slowing down. This year, he released his latest album, Rough and Rowdy Ways (his newest since 2008), and it was announced that Timothee Chalamet would portray him in an upcoming biopic directed by James Mangold (director of Walk the Line, Ford v. Ferrari and Logan).

Dylan’s work has also been a vital part of film culture since his beginning; he composed the soundtrack for films like Pat Garret & Billy the Kid, starred in films like Masked and Anonymous and was portrayed by the likes of Cate Blanchett, Christian Bale and Heath Ledger in I’m Not There. Those are the obvious picks, but here are some of our other favorite Dylan moments in film.

“Hurricane” in Dazed and Confused
“Hurricane” is widely considered to be one of Dylan’s masterpieces, a protest song that encapsulated the history of Rubin Carter’s wrongful imprisonment. That context may be lost on the viewers who first took note of the song when it was used to score Matthew McConaughey’s entrance into The Emporium in the high school comedy classic Dazed and Confused.

The Freewheelin’ Bob Dylan album cover in Vanilla Sky
The eclectic soundtrack to Vanilla Sky includes Dylan’s “4th Time Around,” but it’s the iconic cover image of Dylan’s classic studio album The Freewheelin’ Bob Dylan that plays a major plot point in the film. David Aames (Tom Cruise) finds that in his lucid dream state, he recreated the iconic image of Dylan in the snow without realizing it.

Don’t Look Back (1967)
One of the definitive music documentaries, Don’t Look Back explores the ins and outs of Dylan’s tour in England, showing his interactions with the press, preconcert rituals and the image of Dylan tossing aside cue cards with lyrics to “Subterranean Homesick Blues.” A must-watch for music buffs and cinephiles alike.

“The Times Are a-Changin’” in Watchmen
The 2009 adaptation of Watchmen may not have lived up to some fans’ expectations, as director Zack Snyder lacked the maturity needed to explore the themes of Alan Moore’s graphic novel. However, the film did include one iconic sequence in which Dylan’s “The Times Are a-Changin’” narrates the secret history of superheroes in American history from the end of World War II to the Red Scare.

The Last Waltz (1978) and Once Were Brothers: Robbie Robertson and the Band (2020)
Dylan’s original backup group, The Band, grew to become one of the most influential groups in history, returning for noted collaborations with Dylan himself. Dylan performs with The Band in Martin Scorsese’s concert film The Last Waltz, and Dylan returned to speak about his experience with the group in this year’s documentary Once Were Brothers: Robbie Robertson and the Band.

“The Man in Me” in The Big Lebowski
Thanks to the Coen Brothers, we all hum “The Man in Me” when we’re bowling. Dylan, like The Dude, abides.

No Direction Home: Bob Dylan
Ever had a single question about Dylan, ever? It’s probably answered in No Direction Home, Martin Scorsese’s 3.5-hour documentary that serves as the most comprehensive look at Dylan’s complete history.

“Wigwam” in The Royal Tenenbaums
Wes Anderson is certainly known for his idiosyncratic film soundtracks, and the usage of “Wigwam” when Royal (Gene Hackman) first meets his grandchildren in The Royal Tenenbaums, is one of his most perfect.

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Rolling Thunder Revue: A Bob Dylan Story by Martin Scorsese (2019)
This documentary about Dylan’s 1975 road tour included some stories too good to be true, and that’s because they weren’t. Dylan and Scorsese incorporate a mix of fact and fiction in this unusual experimental film, leaving it to only the true Dylan aficionados to determine the difference.

Steve Jobs (2015) and Steve Jobs: The Man in the Machine (2015)
Steve Jobs was widely known to be one of the biggest Dylan fans out there, having famously used Dylan’s poetry when first introducing the Macintosh in 1984. You can hear Jobs talk about his Dylan obsession in the intimate documentary Steve Jobs: The Man in the Machine, and several Dylan songs show up in Danny Boyle’s excellent biopic Steve Jobs.

Several soundtrack cues and references in High Fidelity
High Fidelity is one of the quintessential films about loving music, telling the story of a list-making music buff (John Cusack) who recounts the songs that influenced some of his toughest breakups. Cusack’s record store coworker, played by Jack Black, chastises a novice record collector for not owning Dylan’s Blonde on Blonde, and several Dylan songs like “Most of the Time” and “Tonight I’ll Be Staying Here With You” play during key emotional moments.

Dylan finally wins an Oscar for Wonder Boys
Dylan has been lauded by awards groups for his entire career, but it took until 2001 for him to become an Academy Award winner. Dylan took home the trophy for the song “Things Have Changed” from Wonder Boys, a highly underrated film about an aging writer (Michael Douglas) looking back at his life’s work. Perhaps Dylan related to this soulful bit of reflection?

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