In recent years, Academy Award-winning filmmaker Barry Jenkins has become one of the industry’s most critically beloved storytellers. His most known work may be Best Picture winner “Moonlight,” but his dazzling adaptations of James Baldwin’s “If Beale Street Could Talk” and Colson Whitehead’s “The Underground Railroad” display a talent that continues to mature. Time and again, he’s proven to be the premiere director for delighting and entrancing audiences with stories about the intersection between identity and romance. Specifically, he is one of the most visually arresting purveyors of Black love on the big screen. 

But “Medicine for Melancholy,” his 2008 debut feature, harkens back to an era where films like Jenkins’ later work were in even shorter supply. The film is a navel-gazing indie romance starring former “Daily Show” contributor Wyatt Cenac and Tracey Heggins as two strangers who spend 24 hours together after having hooked up at a house party. Marketed like Richard Linklater’s “Before Sunrise,” but for active Tumblr users who unironically called themselves “blipsters,” “Melancholy” was a special proposition. At the time of release, the microgenre this film tangentially related to — “mumblecore” — was a low-budget filmmaking trend mostly employed by white hipsters telling slice-of-life stories. To see that kind of film done with a Black cast from a Black filmmaker felt revolutionary for a specific subset of young Black folk.

I remember this film as a sweet little Black-led indie, big on charm, showing Jenkins’ vast potential. Hollywood still has a ways to go in the present day to provide a more diverse array of films from a wider variety of voices and perspectives, but back in 2008? There wasn’t much out at the multiplex for Black people who wanted to see themselves on screen that wasn’t presented by Tyler Perry. For arthouse moviegoers, the pickings were even slimmer. If you consider yourself in any way left of the mainstream center, being Black in artsy spaces could be an alienating experience. Revisiting the film here in 2023, I wasn’t prepared to face the fact that its many conversations about gentrification, interracial dating, and other salient topics were just window dressing for a story about a specific brand of isolation that has (thankfully) began to die off in popular culture.

The film is a navel-gazing indie romance starring former “Daily Show” contributor Wyatt Cenac and Tracey Heggins as two strangers who spend 24 hours together after having hooked up at a house party.

“Melancholy” is a curious time capsule. The two leads are ostensibly star-crossed lovers. Still, in execution, they feel like warring sides of a debate Jenkins is having with himself. Micah (Cenac) is a bearded, bike-riding music nerd who seems incapable of having a conversation that is not some kind of discourse on race and its impact on society. By contrast, Jo (Heggins) comes off less like a character and more like a summary of ideas Micah struggles with. When they first wake up together after their drunken dalliance, Micah is eager to get to know Jo more, but she gives him a fake name and ghosts him. She accidentally leaves her wallet behind like a glass slipper, leading him to cyberstalk her on MySpace and discover that she has a boyfriend. A white boyfriend.

Micah ignores the moral implications ofj their chance encounter because this is like a fairy tale for him, and he’s finally found his princess. After returning her wallet, he convinces her to spend the day with him. She is constantly bombarded by him quizzing her musical opinions, reframing every conversation through the lens of race, and being generally confrontational. He tells her he’s Black before he’s a man and chides her for wanting to visit the Museum of Modern Art instead of the Museum of African Diaspora. (“MoAD, mama, not MoMa.”) Jo is presented as someone gleefully detached from her own racial identity, while Micah is obsessive about it in a way that doesn’t quite ring true. At least, it doesn’t at first.  

Though “Melancholy” was created by the same team of craftspeople that Jenkins has stuck with through his later work, the film lacks the sumptuous visuals cinematographer James Laxton would go on to create. This is partly because this movie was shot for $15,000 three years before digital video cameras started to get really good. Jenkins also made “Melancholy” before he got into Wong Kar-Wai, an influence that informed the more lyrical elements of his later work. (Kar-Wai was a filmmaker known for his bold use of color and his unique atmospheres.) But the rest is really on Jenkins and Laxton’s main motif of choice. The film has this perpetually washed-out, desaturated look with the color purposely dialed back, the brown of the leads’ skin vampirically sapped out for artistic effect. But the saturation returns thematically in moments where Micah and Jo are not so entrenched in a philosophical debate about race.

Initially this comes off as a strange stylistic choice, as if the only time these two can be at peace and look like their true selves is when they’re disconnected from their identities entirely. It feels harmful and limiting until the film reveals that Micah’s obsession with talking about race isn’t borne of a love of his own Blackness but a pronounced jealousy towards whiteness. This comes into sharp focus when the duo visits a dance party at a club that perfectly exemplifies the indie sleaze era, only to be the only two Black people there. This leads to a drunk Micah ranting at Jo about her having a white boyfriend and how unfair it is.

There are some truly touching and memorable moments in “Melancholy” that just showcase two beautiful young Black folks connecting and finding solace in one another. Those fleeting scenes feel like a trailer for what’s to come from Jenkins in his later years. But everything that surrounds them shows how conflicted he must have been at the time and how he had to exorcize his own demons about his place in the world before being able to depict a love between others. 

While it remains weird to watch a Barry Jenkins film that opens with “New Year’s Kiss” by Casiotone For The Painfully Alone, it’s fascinating to be reminded how displaced young Black artists used to be in film and music. We have been able to watch Jenkins naturally evolve from an outsider scratching at the periphery of the Indie Hipster Industrial Complex to an artist paving his own lane — one who tells Black stories that transcend fighting with the same ideas about racism rather than feeling the need to avoid them entirely.

“Medicine for Melancholy” is streaming on AMC+ and DirecTV and is available to rent and purchase on Amazon Prime, Apple, Google Play, et al.