Almost ten years after New York magazine asked “What Ever Happened to Hal Hartley?”, we still don’t have a satisfactory answer. In the 1990s, Hartley established himself as an eccentric torchbearer for American independent cinema and made (more than once) a very specific type of great film. Filtering Gen-X grunge through a punctilious Bressonian formalism, and anticipating the deadpan dolor of Wes Anderson and Todd Solondz, Hartley wrote and directed irreverent date movies for and about self-fashioned intellectual misfits. No other filmmaker has gotten as much mileage out of filming people read. The quotable ennui and well-protected romantic core of these films mark them, perhaps, as embarrassingly earnest totems of youthful self-importance.

Mannered, minimalist and arch, even the director’s best movies can seem a little diffident about their power. Often accompanied by Hartley’s own tinny, melancholic synth scores, they foreground their artifice in order to cloak their optimistic sweetness. Though he favors working-class settings, Hartley strenuously avoids naturalism in favor of a choreographed simplicity. His characters move within tightly composed spaces, intoning their dialogue with a precise, expressionless diction. They are unusually sincere and declarative, often philosophically astute, but they’re rarely listening to each other. “It hurts to breathe,” complains the beaten and bloodied garbage-man poet in Henry Fool (1997). “Of course it does,” answers his friend, lost in an abstract daze.

After that uncharacteristically epic-length magnum opus, one of the most exquisite and poignant dark comedies of all time, Hartley turned his energies toward sketchier, DIY patchworks of half-formed ideas that barely qualified as feature-length. The audience got small, too. But an unexpected bounty of re-releases from Olive Films enables viewers to sample the highlights and missteps of a bold and uncompromising career, and even nurse hopes of a renaissance.

Hartley’s earliest, Long Island–set low-budget features, The Unbelievable Truth (1989) and Trust (1990) (Blu-Ray $29.95; DVD $24.95), owe much of their confidence to his starlet muse, the late Adrienne Shelly. Innocent, insouciant, ironic, beautiful but resolutely unglamorous, Shelly wasn’t just the perfect avatar for the ’90s indie film boom, but also one of the cinema’s most fully realized teenagers. Protecting an open heart with a tart tongue, she confronts everyday injustice with a stubborn sense of conviction. She seems somehow more substantial than any space she inhabits.

The Unbelievable Truth is a romantic melodrama set up as a western. We first meet Josh (Robert John Burke), a convicted murderer and aspiring mechanic who looks suspiciously like a priest, hitching a ride from prison back to his hometown. Shelly plays Audry, a teenage local who shrugs off her bright future—Harvard and a modeling career are her two viable options—in order to obsess over an impending nuclear holocaust. Only logic, common sense and public opinion stand in the way of these star-crossed lovers, but when the movie asks whether flawed human beings are deserving of faith, it answers in the affirmative.

Trust is the darker, more resonant film. In a rapid-fire exchange that accompanies its opening credits, 17-year-old Maria (Shelly) informs her parents that she’s quit school, gotten pregnant and needs $5. In response, her father drops dead. Without a place to stay, Maria crosses paths with Matthew (Martin Donovan), a moody, brilliant electronics repairman who carries a grenade in his pocket at all times. “He’s dangerous because he’s sincere,” Maria says—but more important, he’s so damaged that he won’t judge her predicament. Sketching an escape route for his weary young idealists, Hartley’s film seems to indict an entire world for cruel insensitivity, while offering forgiveness to even the most callous of individuals. His detachment rarely extends to matters of the heart, and Trust is a film bold enough to offer a convincing definition of love in the form of an equation.

Packaged together on a single disc are The Book of Life (1998) and The Girl From Monday (2005) (DVD $29.95), two diverting but uninspired experiments in digital video. The earlier movie, an apocalyptic lark set in SoHo on the eve of the millennium, is a fascinating time capsule of the ugly, blurry, decidedly uncinematic early days of DV, and a foreboding glimpse of a jittery pre-9/11 Manhattan. (The movie ends with a shot of the Twin Towers.) Monday, a blandly anti-corporate sci-fi thriller, looks a lot cleaner but seems devoid of original ideas.

It’s tempting to overstate the modest charms of Meanwhile (Blu-Ray $24.95; DVD $19.95), a lean, wise and engagingly contemporary fifty-nine-minute featurette from 2011, which Hartley made upon returning to Manhattan after a few years of Berlin exile. Funded in part by a Kickstarter campaign and never officially released in theaters, the movie is self-consciously small but by no means uncertain. D.J. Mendel, usually a background member of the Hartley cast, takes center stage as Joe Fulton, a rootless, unflappable bohemian wearing a fedora and a gray goatee. “I acted in a movie once that never got distributed,” he says. “I wrote a novel that almost got published.” He also plays drums in a band, fixes sinks, and plans to import energy-efficient windows from Germany, all while making his way from a lower Manhattan under constant construction to the uptown offices of Hartley’s own Possible Films to grab the keys to a friend’s apartment. (He is, perhaps not incidentally, impoverished.) One wouldn’t exactly call Joe an altruist, but he’s a problem-solver unwilling to let anything broken go unfixed. Same difference?

Meanwhile is a testament to the dependable middleman, the gofer who gets things done without asking for recognition. Some might read this as a flattering self-portrait, but coming from Hartley—American cinema’s most unlikely sentimental humanist—it’s probably a genuine thank-you.