Onscreen, Bob Ross was a one-man symphony of warmth. The artist, known for his instructional PBS series The Joy of Painting, was an emblem of gentle energy, beloved for his ASMR-soft voice, his tranquil energy, and his everyone-can-do-it spirit about painting. But in the documentary Bob Ross: Happy Accidents, Betrayal & Greed, it’s revealed that Ross’s legacy has been embroiled in legal battles—with Ross’s son, Steve Ross, being cut out of Bob Ross Inc., the company that owns and licenses his father’s likeness. It’s a sobering exploration of art and exploitation, and that awful place where commerce and financial greed can spoil an artist’s intentions posthumously. For more films that corner this tough conversation, look no further than these five recommendations, which explore this tetchy territory in both light and dark ways.
Amy
The 2015 Oscar-winning documentary traces the turbulent life of Amy Winehouse, the beloved, beehived chanteuse. Directed by Asif Kapadia, the doc aims to strip away some of the tabloid-driven narratives about Winehouse’s drug and alcohol abuse, as well as the assumption that she was solely responsible for her life careening out of control. It’s a raw look at the star singer, her downward spiral, and the people around her in the last years of her life.
Beltracchi: The Art of Forgery
This 2014 documentary follows titular artist Wolfgang Beltracchi, a man who forged hundreds of paintings by masters like Vermeer and Rembrandt, racking up millions of dollars in the process. His forgeries were masterful, ending up in museums and in the collections of wealthy buyers. The doc, directed by Arne Birkenstock, explores Beltracchi’s arrival to his fraudulent calling, as well as his ambivalence toward swindling the art world, raising questions about the artifice of the industry and the value inherent in mimicked art. (Recommended film chaser: Certified Copy by Abbas Kiarostami.)
Portrait of Jason
On the surface, this essential documentary by Shirley Clarke is designed as a series of off-the-cuff stories, told by the film’s sole, enchanting star: Jason Holliday. He’s a hustler, looking right into the camera and regaling the viewer with stories about his hard-won life, in ways both charming and heartbreaking. But as the documentary goes on, Clarke, Holliday, and Holliday’s partner Carl Lee clash, raising questions about the intent of the documentary and whether Clarke is empowering or exploiting Holliday.
Framing Britney Spears
Among the most used phrases this year is “Free Britney,” a rallying cry to support pop star Britney Spears as she attempts to legally wrest herself from a deeply troubling conservatorship. In this 2021 FX on Hulu docuseries, director Samantha Stark examines how Spears got to this point, following her arc from teen idol to pop supernova whose fame upended her life and mental health. Stark also interviews legal experts and Spears superfans to get a deeper understanding of Spears’s conservatorship, during which the singer has still been expected to do shows and rake in money. It’s a grim exploration of the dark side of stardom—Spears has called the conservatorship “abusive”—made even more complicated by the fact that Spears distanced herself from the doc.
National Gallery
Let’s switch to something lighter. In 2014, documentarian Frederick Wiseman trained his ingenious eye toward the titular London museum as part of his ongoing examination of institutions. In the three-hour film (sprawling, weighty, as all his films are), Wiseman shadows the everyday patrons of the gallery, as well as the curators, restorers, and framers who work there. As the film unfolds, Wiseman deftly raises thought-provoking questions about the nature of art presented in galleries, how guests interact with work and the space, and, more broadly, conversations that the art inspires in both funny and philosophical ways.
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