Back in 2000, Christopher Wilcha was riding high, his "The Target Shoots First" about his ethical conundrum working as a marketer for Columbia House's record club having won Best Documentary at both the Slamdance film festival and SXSW.  But over the ensuing decades, the aspiring documentarian found himself shelving one project after another, his income mostly derived from shooting scores of television commercials.  A moment of reckoning arrives spurred on by Chris’s most recent attempt to shoot a documentary about the New Jersey record store he worked in as a teen, “Flipside.”

Laura's Review: A-

Cowriter (with Joe Beshenkovsky, Adam Samuel Goldman)/director Christopher Wilcha’s second documentary both is and isn’t about Flipside, instead a rumination on whether not attaining the early goals he set for himself means he has failed.  Chris will come to an uplifting conclusion, the filmmaker nothing but happy about the life and family he has built over the years, and while he’s arriving at that, he also ties up all those loose ends stored on hard drives in a closet.  “Flipside” is like a more organic Errol Morris anthology documentary threaded together with life lessons.

Wilcha opens his film with one of his abandoned subjects, Herman Leonard, an 87 year-old photographer of jazz legends and Leonard’s regrets and realizations eerily parallel Wilcha’s own.  As he critiques his own work, assembled for a gallery show, he both sees the things he could have done better and, when guests are assembled at its opening, finds joy in his career being celebrated.  When Wilcha visits the man who commissioned the unfinished documentary, ‘NYPD Blue’ and ‘Deadwood’ writer/producer David Milche, now suffering from Alzheimer’s, in addition to his mini bio on Milche, he will make a moving discovery.

One thing segues into another naturally in this well edited doc, Milche having been introduced to the filmmaker by Judd Apatow, who hired the fledgling documentarian for a ‘making of’ on his movie “Funny People,” a work that was completed only to be shown publicly once before being relegated to a DVD extra.  Then a commercial for a NY bank Wilcha is less than enthused to market (that integrity thing again), allows an opportunity to visit youthful haunts, leading Chris to Flipside, a cramped temple to vinyl whose divider tabs still bear the handwriting of Chris’s old colleague Tracey, and Dan, the man who hired him all those years ago.  Overwhelmed with nostalgia and distraught that a new store also owned by a man named Dan in the same town has drawn most of Flipside’s business away, Chris inspires hope in his old boss by deciding to make a documentary about the place.  Ten years pass.  Chris gets involved with Ira Glass, directing the television version of ‘This American Life,’ a creative rejuvenation, then is asked to make a documentary of Glass’s live show, something the radio personality decides to scrap.

Those unfinished documentaries are only part of the things Chris has saved, all things stashed in a closet at mom and dad’s house, a closet they’ve been begging him to empty.  Ironically, we’ll learn Chris’s hoarding habit was inherited from his father, who also worked in marketing and, astonishingly, once used Uncle Floyd in one of his own promotions.  Uncle Floyd, whose long running cult comedy variety show was a precursor to the likes of PeeWee’s Playhouse, is a regular Flipside customer who creates a jingle for the store in front of Chris’s camera (and was immortalized in David Bowie’s ‘Slip Away’).  Chris tries to rejuvenate interest in Flipside with a social media campaign, but it goes nowhere.  Tracey, his past coworker and girlfriend, advises him to ‘let it go,’ the old store now as decrepit as its owner, now perhaps more of a hoarder than businessman.  When Chris decides to sell his old vinyl, he takes it to Dan’s competitor where he is convinced it will find new life.

All those old things, Wilcha tells us, help preserve the past, but can also be suffocating.  And although he surmises many things his generation holds dear won’t matter to the next, he seems mighty pleased when his teenaged son enthusiastically inherits some of his vintage rock tees.  With “Flipside,” Wilcha both honors the past and embraces the future and the results are both entertaining and moving.

Robin's Review: C+

Oscilloscope Labs opens "Flipside" in select theaters on 6/14/24, expanding in subsequent weeks.  Click here for theaters and play dates.