Chris Wilcha’s new documentary, “Flipside,” is easy to summarize, but it defies summary nonetheless, because it advances by a lurching, associative method that leaves fault lines on the surface of its unity. Feeling stuck in a rut, Wilcha, a successful director of TV commercials, starts shooting a documentary about a record store in suburban New Jersey, Flipside Records, where he worked as a teen-ager, in the nineteen-eighties. From this slender premise, he develops a breezy but prodigious memory piece, encompassing his family background, his artistic obsessions, and his adventures in the movie business.

“Flipside” is stuffed with footage from Wilcha’s voluminous video archives, a trove that he explores to reveal its deeply personal implications. The work is built of fragments, and Wilcha introduces them in a wryly deceptive way. At the start, the movie seems to be a documentary about Herman Leonard, a photographer best known for his images of jazz musicians. His 1948 picture of Dexter Gordon musing amid a cloud of cigarette smoke is now a widely acknowledged highlight of jazz iconography, yet his jazz photographs had their first exhibition only in 1988, when he was in his sixties. When Wilcha filmed Leonard, in 2010, the photographer was eighty-seven and his work occupied pride of place in a big exhibit of jazz photography in Los Angeles. Leonard was also dying of cancer, and Wilcha rushed to shoot as much footage of him as possible.

Now Wilcha pulls the rug out from under the viewer. In a voice-over, he admits that the film about Leonard is one of many that he hasn’t finished, and he tells a chipper, copious story of the various failures that have led him to this confession. In his early twenties, Wilcha was an aspiring documentarian who had taken a corporate marketing job to make ends meet. He carried a small video camera wherever he went—including to the office, where he interviewed his colleagues about their work. The resulting documentary, “The Target Shoots First,” which premièred in 2000, was received well, but making a living as a filmmaker proved hard. (Even a commissioned making-of feature of Judd Apatow’s “Funny People,” from 2009, hardly raised his profile.) He married, had children, and eventually carved out a decent career directing TV commercials. All the while, he kept working on his own documentaries, but kept leaving them unfinished, until one day he grabbed a camera and made up his mind to revisit his past.

All of this autobiographical drama spills off the screen in just a few minutes. Wilcha’s fast-paced voice-over is accompanied by a hectic montage of old footage: New York street scenes, former colleagues at their desks, Wilcha at work on commercials. There are home-movie clips showing his wife and children, and even a riff regarding the great documentarian Errol Morris’s side gigs in advertising. As a filmmaker, Wilcha is a middle-aged man in a hurry. His film dashes from event to event, from character to character, while his spoken riffs and reminiscences convey a sense of urgency—the menace of mortality—spurring him to action.

The crucial irony of “Flipside” is planted in the movie almost as soon as the cherished record store, obsessively organized yet college-casual dishevelled, is introduced. Wilcha says, “The place remains exactly as I remember it.” This amber-like stasis suggests trouble amid the paradise of musical passion. The store was very busy and very profitable in its heyday; now it’s neither, and Wilcha, discovering its parlous state, decides to put his marketing skill to virtuous use and make a film about Flipside to help it stay alive.

Wilcha’s connection with the record store provides a dramatic vehicle for the film to tell a story of art, commerce, and impractical passion, refracted through a few remarkable personalities. There is the owner, Dan Dondiego, Jr.; Wilcha’s high-school friend Tracy Wilson, who succeeded him as Dondiego’s assistant; and, most prominently, Floyd Vivino, a.k.a. Uncle Floyd, a loopily inspired TV creator of the nineteen-seventies and eighties, whose children’s-show parodies started on cable and had one late-night run on network television. Wilcha used to watch him, and so did David Bowie; Wilcha notes that Bowie’s 2002 song “Slip Away” name-checks Uncle Floyd as a forgotten celebrity of yesteryear. Now the once famous but still outrageous Vivino is a regular at Flipside, where Wilcha films him singing comic songs at the keyboard and reflecting on his lonely artistic path.

True to his method of amiable indirection, Wilcha leaps from the store into a rabbit hole of memory (complete with its own Proustian culinary trigger, involving smoked meat). Wilcha’s deepest dive is into his own huge collection of stuff—thirty years’ worth, he says, which fills the closets in his childhood bedroom, in the house where his parents, Pat and John Wilcha, still live. The cache is wildly eclectic, including dozens, maybe hundreds, of matchbooks from hotels and restaurants; obsolete electronics; a scrapbook; boxes full of magazines; concert programs; T-shirts, shoes, jackets; his teen-age driver’s license; a poster for a Nirvana show that he’d attended; tennis racquets and balls; an old baseball mitt; a decades-old airline “barf bag.”

In a sense, “Flipside” is a hoarder’s tale, in which objects, by summoning the past, generate intense emotions in the present. A powerful sense of incompletion looms over the movie, as Wilcha evokes the emotional and experiential surfeit of a lifetime, in all its tragicomic glory. As he unpacks the closet and displays his throwaway treasures, he explains, in a line of arrogant sublimity, why he has accumulated so much: “As far back as I can remember, I always had this feeling that the world was going to forget—and that I was somehow in charge of remembering. And that meant saving everything.”

With this stuff occupying space in the house where his parents live, “Flipside” morphs into a hilarious yet resonant family story. Though John and Pat want Chris to clean out his closet, John is just as much of an idiosyncratic pack rat as his son. He collects stamps and coins, magazines and autographed baseballs, long-obsolete AOL-installation disks. “His most enduring and obsessive collection is of hotel shampoos and soaps,” Chris adds, reflecting—with hilarious redundancy—that perhaps he has inherited his own hoarding tendencies from his father. These stories of stuff are the most wondrous parts of “Flipside,” yet also the ones that fall shortest of their ambition: Wilcha, in his rush to get his story out, never stops to expand on the significance of any one of these objects, never runs out a chain of associations that any of them inspire.

For that matter, Wilcha hits a similar wall of silence regarding music. The essence of memory is built into the very objects of which Flipside is made: records and tapes. Quite possibly more hours of music fill the store and its teeming basement annex than a person with a permanently spinning turntable could listen to in a lifetime. All these physical media preserve past performance for eternal recall. They make Billie Holiday and Janis Joplin live forever—and live forever alongside Belle Barth and Herman’s Hermits. They both safeguard historic artistry and magnify ephemera via nostalgia. Although there’s plenty of music in the film, neither Wilcha nor Dondiego—nor anyone else, for that matter—has very much to say about music itself. More time is spent on the rarity or the value of individual items, the peculiarities of album covers.

Apatow, too, is a recurring character, as filmed by Wilcha in 2009 and interviewed by him again now—and the bourgeois-blues aura of Apatow’s movies looms over “Flipside.” The problem of having too much of the sort of consumer goods and memorabilia that the Wilchas keep is, of course, a class-specific problem; one is unlikely to collect hotel soaps without staying in hotels, and Chris (whose father was a food-industry executive) helped to amass his own teen record collection by sometimes taking his Flipside earnings in records instead of cash. The movie adds, in Wilcha’s voice and in the accounts and laments of other participants, a sharper and odder class assumption regarding family life as a luxury to be bought either with financial success in one’s art (which Wilcha fails to achieve) or with what Wilcha explicitly calls selling out (as with commercials or a corporate job).

In a way, Wilcha’s view of the conflict between family happiness and artistic triumph replays the argument of Cyril Connolly’s 1938 book “Enemies of Promise,” with its famous aphorism that “there is no more sombre enemy of good art than the pram in the hall.” Wilcha’s candid avowal that his personal happiness coexists alongside his artistic regrets gives “Flipside” a bittersweet tinge, albeit one that is ultimately dispelled by the project’s overarching optimism. Wilcha’s hoard of video fragments is, above all, mined for his celebration of the people in his life, past and present. Only survive, the film suggests, and your time will come—provided you have loved and been loved well. It’s a movie of love, and Wilcha’s cinematic embrace enfolds his wife, Elaine Didyk, and their children; the reflective Apatow; Dondiego, whose store endures. Wilson, the shop-assistant successor whose time at Flipside launched a career in the music business, speaks of the store’s uncertain prospects with philosophical candor. Other Flipside patrons drift in and out: friends—and even a competitor—of Dondiego’s, and a neighboring shopkeeper who lifts the veil on a longtime mystery.

The movie’s intertwined themes of memory and art, fame and love, surge poignantly to the fore by way of Wilcha’s ongoing connection with the television writer David Milch (Apatow had introduced them), who now has Alzheimer’s. It was Milch who commissioned Wilcha to film Herman Leonard near the end of the photographer’s life. Leonard, whose work and life (and long-delayed recognition) stand as exemplary lessons in dedication—not least to the photographic negatives that sat under his bed for forty years—gets the moral equivalent of the last word, telling a musician, “That’s what we got: we got the memories.” ♦