Before “The Underground Railroad.” Before “If Beale Street Could Talk.” Before his Best Picture-winning “Moonlight,” there was “Medicine for Melancholy.” The debut feature from writer/director Barry Jenkins, “Medicine for Melancholy” is a mumblecore journey through the streets of San Francisco shared by Micah (Wyatt Cenac) and Jo (Tracey Heggins), two brief lovers who share a day together after a one-night stand. 
Released in 2008, the low-budget film captures a specific moment in San Francisco before it gentrified from a vibrant denizen for young artists into a moneyed landscape composed of tech giants. Amid this violent transition, Micah and Jo are strange travelers traversing a world where they are outsiders to the forces coming through the city and each other. They spend time in Micah’s cramped apartment, where the defining feature is his fish tank; they view art at the Museum of the African Diaspora, they take in a local meeting of residents decrying the shifting face of the city, and eventually, wind into a club where they share an intimately profound slow dance. In the process, wounds concerning the monolithic perception of identity rips open: Is Jo less Black for dating a white man? From what tortured well does Micah’s racial essentialism spring from? 
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Textured in James Laxton’s arresting desaturated cinematography, reflective of the angst felt by Micah, “Medicine for Melancholy” is an engrossing trading of suppositions and a tender march through a doomed infatuation. By virtue of solemn performances from Cenac and Heggins, editor Nat Sanders’ eloquent visual rhythms, and Jenkins’ probing script, it’s a post-soul fantasy that can only end with the reality of its setting’s fate.
Now, the film is entering the Criterion Collection: Its release features a new HD master, an audio commentary by Jenkins, another audio commentary from 2008 featuring Jenkins, producers Justin Barber and Cherie Saulter, and editor Nat Sanders, a new featurette about the making of the film, an essay by critic Danielle Amir Jackson. 
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Jenkins spoke with The Playlist via Zoom about his memories of San Francisco, the picture’s aching dance scene, and how John Waters inspired him to say “yes” to The Criterion Collection.     
You were working at Banana Republic before making “Medicine for Melancholy.” Could you talk about what that time in your life was like?I was very much working at Banana Republic on Grant Avenue at the time. I was even still working there while making the film. But I had been Darnell Martin’s assistant on the film she made, “Their Eyes Were Watching God,” with Ms. Winfrey and Halle Berry down here in Los Angeles. That was like the first two years out of undergrad. And then, after that, I kind of just bummed around the country on trains for a year and wound up in San Francisco because I fell in love there. And so I wasn’t really working on anything film related. I was writing a lot, but I had no job in the film industry. I went from being a phone banker on local political campaigns in San Francisco. And then, I got a job working at Banana Republic, which I did pretty much through the making of “Medicine for Melancholy,” and then even for a little while after.
You just mentioned spending time bumming around the country. How did that inform who you became as a person?It did inform who I became, I think to some degree. I hadn’t really traveled much up until this point. And working at Harpo on this film and being Darnell’s assistant, I then worked in development at Harpo Films for a year. Ms. Winfrey’s really good to her employees. So I had this 401k, which I’d never heard of in my life, and I cashed it in when I decided to quit that job. I took the big tax hit on it, but it gave me, I think it was maybe like $7,000—and I always had been fascinated by this idea of a gap year. For kids of certain backgrounds, you graduated high school, and you go to Europe, or you graduate college, and you go to Europe before you join the workforce.
And so I thought: Oh, what’s the poor kid’s version of a gap year? It was me cashing in a 401k and taking Amtrak trains around the country for a year. It was really cool, man. I got to see places like Chicago, DC, and New York, and I went to Telluride, Colorado, for the third time at the end of this trip for the Telluride Film Festival.
I was just really tired and very lonely. And I didn’t know what to do with myself. It felt like moving was a really good way to figure out what to do with myself. The thing I remember most about that trip is actually being on the train and just looking out the window, listening to really sad music as the country passed by, and understanding that there wasn’t a path for my life, you know? I hadn’t gone to some Ivy League school and then got a job at a firm or went to grad school or anything like that. That just wasn’t possible for me. I had to somehow make a way for myself and I didn’t know how to do it. I didn’t end that trip with any plans, but it really crystallized whatever the malaise was I was feeling in LA.
I was telling my partner a couple days ago that my one regret was when I was leaving undergrad, my guidance counselor told me about taking advantage of this freedom to take two months and sample the world and sample the country. And I was basically like, “Nah, I gotta get a job and pay off these student loans.”Exactly. Exactly. And, you know, that’s one thing that I was always really adamant about. Maybe it was irresponsible. Cause I had student loans as well, and I could have cashed in that 401k and applied it towards my student loans, but I was like: No. To hell with this [laughs] I need to experience some life. I’ll figure out the student loans thing at some other point. I still made my monthly payments. But at that time, I needed to see the world a little bit. In this case, the world of the United States of America.
Up to this point in your career, “Medicine for Melancholy” is your lone original screenplay. Could you talk about the challenges of doing an original as opposed to an adapted, particularly for your first feature.Yeah, I mean, it isn’t an original screenplay, as it’s very directly influenced by Richard Linklater’s “Before Sunrise” series and Claire Denis’ “Friday Night,” especially the latter. We even feature a piece score from Ms. Denis’ film right in the center of our movie. So it was, you know, it’s not an adaptation, but it was still heavily influenced by preexisting work I admired.
I think for me; there was just something going on in my life in San Francisco at the time that I needed to talk about. I just had to make something. Necessity is also the mother of invention, and there was just no way I could have adapted anything for $13,000, which was the budget of this film. So I think, by necessity, it had to just originate from the ground up. But yeah, you’re right. It is an outlier to a certain degree. Maybe I need to get back to these original screenplays once I’m done with the current cycle of my career.
The way you integrate the geography of San Francisco is so wonderful. But I want to zoom in by asking about Micah’s apartment and the location scouting for that.There actually wasn’t any location scouting. Because this movie really came out of a breakup. On that trip, taking these trains around the country, I spent about two months in San Francisco and kind of stumbled into a relationship with this young woman, a friend now. I didn’t know anybody in San Francisco except James Laxton, our cinematographer. So I was meeting his friends and became a little bit of a part of his friend group. Then I had this job being a phone banker in these local political campaigns. The guy, he was my boss, he was a young guy, he introduced me to his girlfriend’s best friend. We just hit it off and became this really intense friend group. 
The apartment when I wrote the film, everybody knew it came out of the heartbreak of this breakup with this young woman, and they all wanted to help me find my way through it. Even though they were all still friends with her, we were trying to remain friends. This is a long way of saying that I didn’t scout that apartment. That apartment was given to me by my ex’s best friend. It was her apartment. I just folded all the elements of it into the character, including, and especially, the fish tank.
The coincidental thing, as well, is my partner had not seen “Medicine for Melancholy,” maybe it was a couple years ago when we first started dating, and I recommended it to her. She got halfway through the film, and she was like, wait, I think I used to live in this building.I’m sure everybody in different age groups have these moments when they feel like it was an iconic time in San Francisco. At that time, you could really be young kids not making a ton of money. That little stretch of San Francisco, it’s not necessarily the Tenderloin, was just full of young people, especially young art students and some young kids who worked in tech before it was like a really booming industry. It doesn’t surprise me that your partner lived in that building. I’ve had other people see the last shot in the film and realize: Holy shit; I know exactly where that is. I lived up the block from there. That area was the center of our life when I lived in San Francisco when I was in this intense relationship.
Much more from this interview on the next page.