Leonard's efforts landed him in a boys' home ("Oh, dude, I could tell you stories") and eventually got him kicked out of school. By some miracle of persuasion, he persuaded his parents that if he earned his GED, they would allow him to go to Mexico to do volunteer work. "I liked the idea of doing social work, but the Peace Corps wouldn't take me," he says. "So I found an organization that would take me at 16, and I just went down with them. Ironically, I taught elementary school for the first six months and then worked for this anthropological institute, doing volunteer work in Chiapas, which, you know, I pulled for the movie."
Leonard drew on more than biographical details for the role of Andrew. The character's wanderlust and inchoate yearning weren't too far off the organizing principle of his own youth, which he explains this way: "I gotta get the fuck out of the suburbs," he laughs. "There was nothing scarier to me than becoming an ordinary meathead. There was nothing more frightening than becoming average, which, ironically, I think, is part of the great serenity of getting older — learning how not unique you actually are."
After Mexico, Leonard knocked around between Seattle and London, developing an interest in photography and getting a little work with his camera, before landing in New York at 19. It was the mid-'90s, and independent films were having their heyday at Sundance. "I stared seeing Hal Hartley films and Allison Anders films and Nick Gomez films, and I'd never really seen art films before. I didn't grow up on Godard and Kieslowski," he says. "When I saw some of those scrappier, more independent, more character-driven films coming out, it felt accessible to me, and that's when I really started the journey of trying to find a place for myself in the film community."
Leonard eventually got a job working at Mystic Fire Video, which distributed the works of "old-school freaks" like Kenneth Anger and Derek Jarman. He was also earnestly delving into the kind of bohemian lifestyle Humpday's Andrew envisions for himself. He did an anti–death-penalty performance piece with Judith Malina from the Living Theater, worked with avant-garde filmmaking legend Jonas Mekas, and smoked a joint with Allen Ginsberg. Then he got strung out on heroin. By the time he was cast for The Blair Witch Project, "it was just another thing that happened in the confluence of events of being young and really high in New York and trying to figure to what I wanted to do and what my voice was."
When Blair Witch arrived at Sundance in 1999, Leonard had hit the skids and was in rehab. He was three months sober and living in a halfway house in Los Angeles when he appeared on The Tonight Show to promote the film. When he emerged from the halfway house, he found himself in that vast hinterland of Hollywood — a working actor doing intermittent TV roles and appearing in films of small consequence for years on end.
In the year prior to being cast in Humpday, Leonard had reached the end of his rope. A collaboration on a labor-of-love documentary project about the so-called "Beautiful Losers" art movement had turned sour, he had his heart broken "in a dysfunctional relationship," and financing for a film he was set to produce and direct fell through just before shooting was scheduled to begin. "There was never a riper time to dig in and figure out how to at least try to never put myself in that position again, and a lot of that had to do with self-examination and figuring out where I was complicit in my own downfalls," he explains.
All of which made Leonard uniquely suited to chart Andrew's internal landscape: "I got to do a project like this because of the emotional place that my own life was in, and I think doing a project like this helps to reinforce any personal work I'm doing on myself." A lot of that work, he says, is about "the ongoing journey of trying to figure out who the fuck you are and what your purpose on the planet is, what our generation's version is of what it means to be a man."
It's in this way that Humpday's potentially ludicrous setup is actually a bait-and-switch, allowing for a refreshingly sweet examination of gender, sexual identity, and friendship. The lead characters are never more vulnerable with each other than when they've finally alpha-dogged themselves into a corner. I suggest the ultimate message could be that friendship is gay, even for two hopeless heteros. "In a great way. Friendship is gay. That should have been the tagline, dude," Leonard laughs. "I'm sure a lot of the guys I grew up with would punch me in the face for saying this, but I feel really lucky to have grown up in a generation where the archetypes about what it means to be a man have started breaking down and expanding."
I tell Leonard that as the film closes on an image of Andrew, alone with his thoughts about what the future may hold — an image that evokes Dustin Hoffman in the last scene of The Graduate — I was left with a profound sense of dread about where he goes from there.
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