There’s something vaguely mournful, if not altogether sentimental, about Mark Cousins’s new documentary The Eyes of Orson Welles, a two-hour love letter to the legendary director. It starts with the plaintive notes of an organ playing the baroque Adagio in G Minor coupled with a spectacular aerial shot of Lower Manhattan. The camera glides contemplatively across the skyline from above, while Cousins delivers his slow, lilting voice-over commentary—first made famous in his sprawling documentary, The Story of Film: An Odyssey (2011), a 15-hour tour of motion pictures by an uncompromising cinephile. Here he speaks directly to Welles in the second person, explaining to him that something is missing from this landscape. That something is the Twin Towers. “All things come to an end, don’t they?” he asks. “People, buildings, cities. That was one of the big themes in your movies.”

Cousins first encountered Welles’s work as a young boy, watching Touch of Evil (1958) on television in his native Northern Ireland. “I didn’t understand it, but I swooned,” he confesses, some 40 years later. “You threw a rope to me, when I watched it, Orson.” To this day, whenever he’s anxious, Cousins hums the tune played on the pianola in that film (“a sultry lullaby of sorts”) to calm his nerves. Although upon first viewing Cousins didn’t quite recognize the racial and sexual politics of the film, not to mention the apocalyptic and oddly prophetic nature of its story, he loved the film’s “seedy atmosphere, its rooms and twisted choreography.” Welles’s work may ultimately be perceived as “jagged and fractured,” in Cousins’s estimation, but that doesn’t make it any less beguiling.

Divided into five parts, The Eyes of Orson Welles begins with a documentarian’s conceit of sorts: the discovery of a box of drawings and sketches by Welles, who began painting as a nine-year-old. His daughter Beatrice had kept the box in a storage unit. As Cousins goes through it, he looks at Welles’s life and career, refracted through his art—dozens of charcoal drawings, portraits he drew feverishly on an ocean liner to Ireland as a teenager (“Looking at Irish people was training you to look, to draw”), abstract sketches from a subsequent trip to Morocco. Cousins repeatedly returns to an arresting photograph, more candid than posed, of Welles in his twenties. It captures the director, wide-eyed and handsome, looking straight at the camera while leaning on one arm in repose, dressed fashionably all in black. He is full of curiosity and ambition. The image becomes a leitmotif for the film, filling out the frame with haunting frequency. This is not the later Welles, the portly fellow who famously made Paul Masson wine commercials and who by then was something of a former king forced to abdicate the throne, not quite a sell-out but also no longer a wunderkind. No, this is Orson Welles the artist, orator, and magician, whose outsize imagination and intellect proved irresistible.

While still in his teens, Welles was encouraged by his guardian, a physician named Maurice “Dada” Bernstein, to study drawing at the Art Institute of Chicago, where he purportedly finished thousands of sketches in his drawing studio on Rush Street. Cousins shows how Welles’s experience in that city, amid the skyscrapers, taught him to look up. This perhaps offered an aesthetic model for his later film work: craning upward in Citizen Kane (1941) or shooting from an extreme low-tilt in Mr. Arkadin (1955) and The Trial (1962). Cousins also brings the camera inside the Art Institute to show affinities between the main gallery’s translucent ceilings, which allow light to seep in from above, and the ceilings designed for The Trial, shot in the abandoned Gare d’Orsay in Paris, as well as those in Kane. Similarly, the miniature rooms on display at the Institute bear a striking resemblance to the interior sets used on Kane and The Magnificent Ambersons (1942).

Much of the film serves as an exercise in formal analysis, an occasion to trace lines to exemplary moments in the personal, aesthetic, and political life of the filmmaker. Cousins is particularly keen on returning to places of joy, of preindustrial purity and innocence. We are thus treated to an old postcard of the Sheffield Hotel in Grand Detour, Illinois, which Welles’s father had owned, and which later burned in a fire. Grand Detour was a place that Welles once held dear, perhaps even regarded as a “first love,” calling it “one of those lost worlds, one of those Edens that you get thrown out of.” Cousins is quick to compare it to the “snowy Eden” of young Charlie Kane, shouting with glee outside Mrs. Kane’s Boarding House, bundled up in his muffler and pulling his Rosebud sled behind him. Then, too, there’s the Christmas card scene in The Magnificent Ambersons, another moment of giddy, romantic frolicking in the snow. But “paradises don’t last,” insists Cousins, as he shows us the squalor that’s taken root on the same street corner where the RKO studio, home of that sound stage on which the winter wonderland was created, once stood.