Awesome Art Documentaries Everyone Should See

| © Expressions United Media
Marnie Sehayek

Next time you’re scrolling through Netflix hoping for a category like ‘Films That Will Make Me More Cultured That Will Also Not Put Me To Sleep’, refer to this list. The artists illustrated below have left indelible marks on art and culture and their documentarians – who sought to tell the artists’ respective stories, whether video artist or journalist, lover or friend – lend a sense of style to what can sometimes be a yawning genre. So read on and enjoy!

The Legend of Leigh Bowery

Award-winning video artist Charles Atlas turns his lens on Australian-born artist Leigh Bowery. Is Bowery a performance artist or an avant-garde fashion designer or a 1980s London club scene icon? In reality, he revels in the rich, liminal space of being all of the above. Bowery’s influence is varied and sprawling; he was muse and model to acclaimed portrait painter Lucien Freud as well as planting aesthetic references for photographer David LaChappelle and even Lady Gaga to pick up years after his AIDS-related death in 1994. Bowery’s gender-bending and fashionable eccentricity were prescient predecessors to our current cultural moment. Friends and family provide commentary and context in this documentary, among them Boy George and Damien Hirst, and weigh in on Bowery’s eternal style.

Guest of Cindy Sherman

Photographer Cindy Sherman is a master of disguise. That’s why the personal nature of this documentary is so appealing: it peels back the mask that is Sherman’s modus operandi. Paul Hasegawa-Overacker (a.k.a. Paul H-O) observes his relationship with Sherman, whose eventual mega-art-stardom overshadows Hasegawa-Overacker’s own meagre claims to fame, namely the 1980s public-access television show he hosted, Gallery Beat. Armed with wit and charm, Hasegawa-Overacker examines the art world of yesteryear through the demystifying, intimate lens of a sustained and up-close encounter with an art luminary.

Ai Weiwei: Never Sorry

The poster for this film shows Chinese conceptual artist Ai Weiwei giving the middle finger to his government, which, to make a long story short, is what takes place in Alison Klayman’s insightful documentary into the artist’s world. For Ai, art and activism are not mutually exclusive terms, as he goes head-to-head with the government’s repressive tactics at every turn through art and social media. Despite no small odds – Chinese authorities shutting down his blog, beating him up, bulldozing his studio, and holding him in secret detention – Ai continues to be a seminal voice for freedom of expression and human rights.

Jean-Michel Basquiat: The Radiant Child

Making the jump from the street to the gallery may seem ordinary these days, what with street artists like Shepard Fairey, Retna, and Banksy being household names in the art world. But back in the 1980s, Jean-Michel Basquiat’s transition wasn’t as much of a given. In this film, documentarian (and Basquiat’s dear friend) Tamra Davis has revealing conversations with the artist in one of the only interviews he ever gave, about his gaining traction and fame, dealing with being black in a predominantly white art world, and befriending Andy Warhol. Zooming out, Davis balances the film with interviews and archival footage of important players in New York City’s downtown scene. The film is a thoughtful window into the artist’s life and art.


Robert Crumb is widely considered to be one of the best – if not the singular best – cartoonists in American history, giving life to notable characters like Fritz the Cat, Mr. Natural, and the Keep On Truckin’ strip, to name just a few of his contributions. For this film, director Terry Zwigoff (Ghost World, Art School Confidential) followed the underground comic hero for nearly a decade, interviewing the artist in addition to his friends, family, and contemporaries. What results is a deep examination of Crumb’s psychology and how it shaped his uniquely penetrating and enduring satire of American society.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

Edit article