Timothée Chalamet has been gaining widespread acclaim for his performance as Bob Dylan in A Complete Unknown, which will surely lead to many people discovering the enigmatic folk singer for the very first time. While Dylan has always been an inscrutable enigma wrapped up in a mystery, plenty of feature films, documentaries, and unusual releases give insight into his life as an artist and pop culture icon. Some Dylan films lay the groundwork to understand his status as the voice of his generation during the 1960s, while others will provide context for the challenges of his later career.

As a filmmaker in his own right, Dylan has been involved in many films that play with or recontextualize his legacy as an elder statesman of rock ‘n’ roll. Dylan has been the subject of movie legends like Martin Scorsese or Todd Haynes, there’s a fascinating world to explore when it comes to Dylan and cinema.

10 No Direction Home (2005)

Directed by Martin Scorsese

For viewers who are excited to see Timothée Chalamet in A Complete Unknown but don’t feel like they have the cultural context for Bob Dylan during the 1960s, then the best place to start would be with Martin Scorsese’s No Direction Home documentary. As a chronicle of Dylan’s career through the 1960s and up to his reported motorcycle accident in 1966, No Direction Home puts Dylan’s unmatched place in 20th-century American popular music into perspective in a way that’s digestible to a newcomer. This documentary covers the same period as A Complete Unknown and addresses all the essential historical details.

Much like A Complete Unknown, the title No Direction Home comes from the lyrics of Bob Dylan’s “Like A Rolling Stone,” where he sings: “How does it feel? To be on your own, with no direction home, a complete unknown, like a rolling stone.”

No Direction Home aired as part of the American Masters series on PBS and continues Scorsese’s longstanding association with Dylan, which can be traced to his concert film The Last Waltz featuring Dylan and his former backup group, The Band. Scorsese clearly has a great love for Dylan’s work and legacy, and No Direction Home painted a vivid portrait of the artist while still maintaining his mysterious appeal. If audiences want to know why Dylan was perceived to be the voice of his generation, No Direction Home answers this question.

9 Eat The Document (1972)

Directed by Bob Dylan

Bob Dylan always exerted extreme control over his image and how he’s been presented in the media. This was certainly the case for the unreleased documentary Eat the Document, which was shot under Dylan's direction by the Don’t Look Back filmmaker D. A. Pennebaker and which cataloged his 1966 European tour with the Hawks. The release of Eat the Document was delayed after Dylan’s motorcycle accident, and although the singer later edited the movie himself, ABC rejected it (via The New York Times) and said it was incomprehensible for a mainstream audience.

However, unauthorized bootlegged copies of Eat the Document are in circulation, and it gives a fascinating insight into Dylan’s hectic life in 1966, which was characterized by consistent touring, non-stop songwriting, and heavy drug and alcohol use. Eat the Document includes a fascinating encounter between an inebriated Dylan and John Lennon in the back of a limousine where the Beatles singer encourages him to “pull yourself together.” With Dylan clearly on the verge of a major burnout, Eat the Document showcases the dark reality of Dylan’s rapid rise to fame that’s depicted in A Complete Unknown.

8 Pat Garrett And Billy The Kid (1973)

Directed by Sam Peckinpah

Bob Dylan represents something essential about the nature of Americana, so it made sense that he’d make his dramatic acting debut in Sam Peckinpah’s Western Pat Garrett and Billy the Kid. With two musical icons in the mix, Kris Kristofferson as Billy the Kid and Dylan as the mysterious Alias, these two performers stole much of the limelight from James Coburn as Pat Garrett. Pat Garrett and Billy the Kid was a glimpse into the lawlessness of the Wild West, which Dylan had already explored in music, like his fictionalized take on the real-life outlaw John Wesley Hardin.

Pat Garrett and Billy the Kid featured one of Dylan’s best acting performances, but it was also notable for his soundtrack album, which included “Knockin' on Heaven's Door,” one of his most covered songs. This cult classic Western movie featured an older Dylan than the one Timothée Chalamet portrays in A Complete Unknown. However, as such an enigmatic figure whose life story could carry several feature films, if James Mangold wished to make a sequel, then Dylan’s first attempt at becoming a Hollywood star would be an interesting premise.

7 Rolling Thunder Revue: A Bob Dylan Story By Martin Scorsese (2019)

Directed by Martin Scorsese

Martin Scorsese already made one of the best documentaries about Bob Dylan in the 1960s with No Direction Home, so fans were excited when he released his take on Dylan’s 1975 tour in 2019. However, much like Dylan himself, nothing about the Rolling Thunder Revue was straightforward, as this documentary blended fact and fiction to tell a story where nothing was certain. With much of the visuals compiled of outtakes from Dylan's 1978 film Renaldo and Clara, Rolling Thunder Revue featured new interviews with Dylan and others associated with the tour.

While all this sounds straightforward enough, the lines between fact and fiction began to blur as Rolling Thunder Revue introduced characters like the fictional filmmaker Stefan Van Dorp or Sharon Stone, falsely claiming she ed the tour at the age of 19 despite never crossing paths with Dylan during the 1970s. Rolling Thunder Revue was a truly strange mockumentary that showcases Dylan has not lost any of his unique sense of humor in the decades since the events of A Complete Unknown took place.

6 Renaldo And Clara (1978)

Directed by Bob Dylan

Bob Dylan spent the fall of 1975 on his outrageous stage tour, the Rolling Thunder Revue, which featured a traveling assortment of musicians, including Joan Baez, Ramblin' Jack Elliott, Patti Smith, Joni Mitchell, and many more. During this time, Dylan also opted to direct his own feature film, which he co-wrote with the acclaimed playwright Sam Shepard. The result of this endeavor was the sprawling avant-garde work Renaldo and Clara, an inscrutable mix of concert footage, documentary interviews, and dramatic fictional vignettes that clocked in at a whopping 232 minutes.

Renaldo and Clara was intended to reflect Dylan’s life and lyrics and was as incomprehensible as some of his most surreal songs. The film was released in its original four hour cut in 1978 to an overwhelmingly negative response from audiences and critics. While the full version of Renaldo and Clara is hard to track down today and has mostly been withdrawn from circulation, those who wish to seek it out will see a fascinating document of Dylan in the midst of a highly creative period, as well as the breakdown of his marriage to his then-wife Sara Lownds.

5 Hearts Of Fire (1987)

Directed by Richard Marquand

The late 1970s and early 1980s saw Bob Dylan alienate many of his fans as he released a string of Jesus-loving Christian albums in a period often described as his gospel era. Dylan’s born-again period signaled the beginning of a downturn in his career as his usually distinctive style was bogged down in 1980s production, and by 1987, he felt like a relic from the past. All these downward turns influenced Dylan’s decision to star in Hearts of Fire, a music drama where he played a washed-up rock star whose teenage lover leaves him for synth-pop sensation.

While Hearts of Fire may sound like an intriguing retooled version of A Star is Born featuring Dylan, it perfectly encapsulates everything wrong with the once-celebrated voice of his generation. While A Complete Unknown showcased Dylan’s meteoric rise to the top, Hearts of Fire featured him at the lowest point in his career. However, this much-maligned film was worth checking out just to hear Dylan utter the ironic line: “I guess I was never one of those rock and roll singers who was going to win any Nobel Prize.”

4 Masked And Anonymous (2003)

Directed by Larry Charles

By the time Masked and Anonymous was released, the dark days of the 1980s were long over, and Bob Dylan had earned his place as an elderly statesman of rock. Following the success of Oh Mercy, Time Out of Mind, and Love and Theft, Dylan cemented his reputation as one of the few living icons of the 1960s who remained creatively relevant into the 21st century. This was why it was so exciting when he returned to feature films with a starring role in Masked and Anonymous, which he co-wrote with Seinfeld and future Borat director Larry Charles.

Dylan played Jack Fate in Masked and Anonymous, a film whose strange and cryptic style felt like it was straight out of a Bob Dylan song. With a star-studded cast including Jeff Bridges, John Goodman, Penélope Cruz, and Jessica Lange, there was no shortage of major names who wanted to appear alongside Dylan in a film. While Masked and Anonymous was badly received upon release, like many of the singer’s projects, its reputation has only grown with time, and looking back, it’s a fascinating insight into how Dylan views his own legacy in the modern age.

3 Shadow Kingdom (2021)

Directed by Alma Har'el

Throughout the 21st century, Bob Dylan has pulled away from the public eye and instead focused primarily on touring, only doing around one major interview for each new album he releases. With a strict ban on video recording at most live shows, it’s difficult to even catch a glimpse of Dylan in recent years, which made the release of the concert film Shadow Kingdom so interesting. This unusual live showcase was shot on a soundstage during the Covid-19 pandemic and featured Dylan singing renditions of his early career songs in an intimate club-like setting.

For viewers who are only learning about Dylan’s importance from the press tour of A Complete Unknown, watching Shadow Kingdom is a great way to get insight into his modern style and sound. While Dylan sang many of his best-known songs in Shadow Kingdom, his renditions are totally different from the studio recordings and represent an older artist reimagining his songs continually. Dylan’s late-career live output can be quite alienating because he has changed so much since the 1960s, and Shadow Kingdom helps bridge the gap between his early and late career.

2 I’m Not There (2007)

Directed by Todd Haynes

The life of Bob Dylan has so many different facets that the only way to make a movie about him would be to focus on one era, like in A Complete Unknown, or to completely reimagine the structure of a typical music biopic. This was exactly what Todd Haynes opted to do with his extraordinary film I’m Not There, which cast six actors depicting different facets of Dylan's public personas. This included the extraordinary decision to have Cate Blanchett play the 1960s, strung-out, sunglass-wearing version of Dylan as he’s accused of selling out for going electric.

I’m Not There featured several major stars, with Christian Bale playing the born-again Bob of the 1960s and Richard Gere portraying the Western version of him from Pat Garrett and Billy the Kid. All these reimaginings of Dylan had different names and were meant to reflect the essence of the singer’s life and legacy rather than a true historical . For those looking for a more experimental take on Dylan’s story than what’s seen in A Complete Unknown, I’m Not There is the perfect alternative.

1 Don’t Look Back (1967)

Directed by D. A. Pennebaker

For viewers wishing to gain insight into the era of Bob Dylan’s life depicted in A Complete Unknown, then Don’t Look Back is essential. This documentary of Dylan's 1965 tour in England is a time capsule into an extraordinary moment of the 1960s, as this folk singer's fame was exploding and the world witnessed the dawning of one of the most essential figures rock ‘n’ roll music has ever seen. As an of Dylan on the precipice of going electric, Don’t Look Back showcases how he plays with the media and carves out his calculated persona.

Don’t Look Back was as much an acting role for Dylan as any feature film he appeared in and was an impressive document of art meeting fame as the press struggled to make sense of his enigmatic presence. From his interactions with the likes of Joan Baez and Donovan, Don’t Look Back gives viewers a glimpse into Dylan’s creative process as everyone around him was left dumbfounded by his seemingly endless talent. Don’t Look Back is the greatest record music lovers have of Dylan during the 1960s and is one of the best music documentaries ever made.

Sources: The New York Times