Matthew Porterfield's Putty Hill

The Chicago Underground Film Festival, which takes place Wednesday, June 6, through Sunday, June 10, celebrates its 25th anniversary this year. We take a look back at some notable features that screened in previous editions of the festival, movies demonstrating that “underground” is a happily elastic term.

A dog-eared valentine to indie rock slackerdom, this 1994 black-and-white feature centers on a disaffected young woman in Louisville who impulsively makes off with her brother’s van full of musical equipment and, along with some similarly aimless pals, embarks on a guerrilla concert tour of the southeast. They can’t play a lick, but they’re perfectly capable of sleeping on floors and scraping together change for convenience-store food, which gives them all the cred they need. First-time filmmakers Suki Hawley and Michael Galinsky were veterans of the New York rock scene, yet their movie manages to be wryly satirical without compromising its low-grain verisimilitude; they later graduated to political documentary with the excellent Horns and Halos. Hawley directed; with music by Freakwater, Sleepyhead, and the Grifters. 82 min. —J.R. Jones

The Delicate Art of the Rifle
D.W. Harper directed this 1996 feature about the infamous Charles Whitman, who climbed a Texas tower in the mid-60s and shot people at random. Screenwriter Stephen Grant (who also plays the crazed killer) updates the story to the present and tries to milk it for absurdist humor, telling it from the bemused viewpoint of the killer’s nerdish roommate. Ambitious and inventive, but unevenly acted and overextended, this will certainly hold one’s interest, despite its hit-or-miss qualities. 93 min. —Jonathan Rosenbaum

It’s obvious that Ben Berkowitz and Benjamin Redgrave were thinking of John Cassavetes’s Shadows (1960) when they made this impressive Chicago-based feature (1999). Both features grew out of acting classes, and both have titles that relate allegorically to their themes, with sexual orientation playing a role in Straightman similar to that of race in Shadows. Berkowitz (who also directed) plays the heterosexual manager of a comedy club, and Redgrave plays his best friend, a construction worker; the two become flatmates after losing their girlfriends, and only later does Redgrave admit that he’s gay. The two Bens dominate the proceedings, making this more a two-man show than a genuine ensemble piece. None of the other able actors is given enough time or leeway to establish herself or himself as completely as we might like, and the plot doesn’t seem fully shaped and concludes rather awkwardly and arbitrarily. But both these cavils are minor next to the sizable achievements of this feature. 101 min. —Jonathan Rosenbaum

The Target Shoots First
Christopher Wilcha’s fascinating feature-length video (2000) reminds us how seldom we’re allowed to see certain businesses operating from the inside. Wilcha, a 22-year-old college graduate and alternative-rock enthusiast, was hired by the Columbia Record and Tape Club—apparently as a fluke—to help launch a whole new niche-marketing division, which brought him face-to-face with the contradictory meanings of the term alternative once it’s been embraced by the mass market. He brought his video camera to work every day, and what emerges are selective glimpses of—and thoughtful reflections on—his extended stint with the company. He notes the mythological and practical differences between various floors of the company’s Manhattan headquarters and shows what happens at the national headquarters elsewhere; he describes how the club’s guide is written and edited, how changes in staff affect his own peace of mind, and how certain people behave at parties and staff meetings. This is a good deal better than your typical 60 Minutes segment, registering as autobiography as well as investigative reporting, and Wilcha’s wry intelligence kept me glued to the screen. 70 min. —Jonathan Rosenbaum

Migrating Forms
Chicagoan James Fotopoulos directed this stark 1999 drama in which a man and woman meet repeatedly in a mostly bare room for nearly wordless and apparently passionless sex, filmed in low-contrast black and white. Usually when they commence, an electronic screeching begins and Fotopoulos cuts to the man’s cat, which appears to be watching the action with greater affect than either human displays. The woman has a grotesque growth on her back, and soon the man is infected by it. A few mundane incidents, such as an exterminator wanting to spray the apartment for roaches, take on wider significance later, as when the man finds a roach and myriad dead flies. Flickering white and shots of water open and close the film, enclosing the action like a prison cell; Fotopoulos seems to suggest that life itself is a form of disease—hopeless, meaningless, and ugly. 80 min. —Fred Camper

Benjamin Smoke
Jem Cohen and Peter Sillen’s 1999 documentary pays tribute to Robert Dickerson—better known as vocalist Benjamin Smoke of the offbeat Atlanta band Smoke—who died of AIDS shortly after the film was shot. It captures his unaffected honesty and charm and his poetic way with words, but what’s really fine is the filmmakers’ sensitivity in blending all kinds of disparate material. Patti Smith, Dickerson’s first inspiration, let Smoke open for her in Atlanta, which provides the film with a satisfying climax, yet the talking/singing/playing/goofing-off heads that precede this apotheosis are just as watchable (and listenable). 72 min. —Jonathan Rosenbaum

Nice Bombs Chicago filmmaker Usama Alshaibi grew up in Iraq and the U.S., and although he recently became an American citizen, his personal video documentary (2006) has plenty to say about the day-to-day existence of his Baghdad relatives, whom he visited in 2004. Distance tends to simplify our view of anything, and this video humanizes the situation on the ground mostly by complicating it: in a voice-over Alshaibi says he’s often asked what “the Iraqis” think, but by the end this question has become as meaningless as asking what “the Americans” think. Much of his previous work has been experimental, but this becomes formally adventurous only near the end, as he converses by phone with a cousin who tells him how much worse the situation has been growing. 76 min. —Jonathan Rosenbaum

Putty Hill
With Hamilton (2006) and now this second feature (2010), Baltimore filmmaker Matthew Porterfield has proved himself adept at the sort of richly observant regionalism that defined David Gordon Green (George Washington) before he chucked it all to go Hollywood (Your Highness). The story takes place one summer in a working-class, semirural Baltimore suburb, and Porterfield introduces his young, directionless characters with documentary-style Q&As that are disarming in their candor and authenticity. The kids are preparing to attend the funeral of 26-year-old Corey, who’s died of a heroin overdose, and the movie’s beauty and melancholy spring from the fact that while many of these kids are sweet and sensitive, their lives also seem destined to dead-end in one way or another (if they haven’t already). 85 min. —J.R. Jones

The Color Wheel
Shot on 16-millimeter, this cheapo black-and-white road movie (2011) by Alex Ross Perry is the most compelling New York indie I’ve seen since Ronald Bronstein’s Frownland (2007). An angry young looker (Carlen Altman) and her tall, dorky brother (Perry) set off on a car trip to reclaim her stuff from the broadcasting professor who’s just terminated their teacher-student romance. Most of the movie consists of the two siblings mercilessly needling one another about their gaping emotional flaws, and the nasty banter is so cruel, knowing, and funny that only in the end does one realize it’s sheer compulsion. Altman and Perry wrote the movie together, and despite the relentless verbal combat, they’re smart enough to let a devastating scene at the end play out in near silence. 83 min. —J.R. Jones

Two Years at Sea
The first feature-length effort (2011) by noted experimental filmmaker Ben Rivers demonstrates such mastery of the image that it’s worth seeing for the textures alone. Shooting on black-and-white celluloid, he creates a hazy, granulated look that suggests an old daguerreotype come to life, which feels appropriate considering his subject is a human anachronism. Former sailor Jake Williams (whom Rivers first documented in the 2006 short This Is My Land) lives a solitary life in the Scottish wilderness, scavenging for food and constructing items from industrial refuse. This is filled with gorgeous natural imagery, but it isn’t an environmentalist statement or even a straight documentary: in one of the more audacious sequences, Williams gazes in wonder as his trailer floats to the top of a tree. 90 min. —Ben Sachs