The Graduate (1967)

A generational emblem more than a movie, the Mike Nichols classic The Graduate captures the essence of alienation and social incompleteness as only films made in the late 1960s and early 1970s can. Dustin Hoffman became a star in the unlikeliest of circumstances: as an aimless college grad who cannot get a fix on what he wants out of life. He is seduced by a family friend (Anne Bancroft), and is then pressured into dating her daughter (Katharine Ross); as life gets more complicated, he searches madly for any reason at all to choose one destiny over another. Credit is due to 1967 audiences, who saw themselves in this ambivalent portrait, and who dared to ask big questions of themselves and their movies. Picture, if you can, the new millennium’s freshly graduated degree-holders facing the same choice.

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Heathers (1989)

A massively clever, thick-as-a-brick screenplay by Daniel Waters gave this teen satire plenty of ground to tear up—it mockingly endorses, among other things, in-school murder, terrorism, and teen suicide, while dishing homosexuality, teachers, parents, football, and bulimia—all in fun, of course. Winona Ryder’s wary clique-follower hangs with the cool, big-haired girls of 1980s Westerberg High (named after Paul, famed lead singer of the Replacements), and has her homicidal fantasies realized by new kid Christian Slater (doing a killer Jack Nicholson). Conceptually Heathers is outlandish, right up to the climactic bomb, but it’s also endlessly inventive, line for slangy line, and the feeling of teen social crisis is there.

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Office Space (1999)

Office Space (Photo credit: Wikipedia)

A brilliantly unassuming comedy by Beavis and Butt-head creator Mike Judge. A stressed-out software drone (Ron Livingston) takes a hypnotic suggestion at its word and ceases to care about his job—doing it or keeping it or even showing up—a disorienting mode of behavior that’s mistaken for self-directed confidence by the consultants who’ve been hired to determine who gets the ax. Although ignored upon its release, Office Space has become the definitive white-collar movie of techno-era America. Gary Cole’s smarmy manager, in particular, will leave a heel print on your brain. With Jennifer Aniston.

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How to Get Ahead in Advertising (1989)

Many jobs call for ethical compromise, and in How to Get Ahead in Advertising, a devilishly uncomfortable comedy, an adman’s anxious doubts about his job manifest as a giant pimple on his shoulder. Soon enough, the zit sprouts eyes and a mouth, and begins persuading him toward new heights of capitalistic venality. As both perpetrator and victim, Richard E. Grant is a whirlwind of neurotic craziness.

How to Get Ahead in Advertising (Photo credit: Wikipedia)

Welcome to the Dollhouse (1995)

Welcome to the Dollhouse (Photo credit: Wikipedia)

If you don’t remember the killing fields of the seventh grade, Welcome to the Dollhouse is a reminder. Todd Solondz‘ movie opens in the Theater of Cruelty of the junior high school cafeteria, where finding somewhere to sit, and people who will let you sit with them, has all the shivery dread of being lost in a police state without ID. The camera slowly circles around eleven-year-old Dawn Weiner (Heather Matarazzo), standing there holding her tray and surveying the combat zone, her bespectacled face a knot of huddled horror. You’ve been there.

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Little Miss Sunshine (2006)

Jonathan Dayton and Valerie Faris’s indie hit (pulling in nearly a 1,000 percent return on investment in a year in which Mission: Impossible III couldn’t even break even) has a familiar outline: a contentious, eccentric extended family hits the

Little Miss Sunshine (Photo credit: Wikipedia)

road in a puttering VW bus—in this case, to participate in that most revolting of American rituals, the preadolescent beauty pageant—but it’s executed with consummate wit and Swiss timing. The charm of Little Miss Sunshine might boil down to the cast: give pros like Alan Arkin, Steve Carell, Toni Collette, and Greg Kinnear some open road, and they will race like the devil.

Real Life (1979)

In 1973, PBS ran a documentary series called An American Family, about a real upper-middle-class nuclear unit, shot in the family’s home. But how could that have been “reality,” asks comic Albert Brooks in his first film, which duplicates the scenario to wicked, double-edged-sword effect. As usual, Brooks is the ogre-ish primary target, but the era’s relationship to TV and fame are also bludgeoned into pulp.

Smile (1975)

Middle America was cool in the 1970s—or at least cool enough to be satirized up and down for its cheesy, oblivious silliness in films like this Michael Ritchie interrogation, which tears apart a second-rate California beauty pageant, from recruitment to training to the final face-off. Everyone—contestants, parents, organizers, judges, choreographers, peeping toms, ad infinitum—gets a vicious lashing, but Ritchie never strains or caricatures. This is how it was, and probably in many ways still is, and it’s hilarious and dismaying because you believe every frame.

Being John Malkovich (1999)

Perhaps the closest a Hollywood movie has ever gotten—and probably will ever get—to the free-associative shotgun spray of Salvador Dali’s and Luis Buñuel’s Un Chien Andalou, this first film by the team of director Spike Jonze and screenwriter Charlie Kaufman is an ingenious, incredibly entertaining, Rorschach blot of a metacomedy that says a truckload about celebrity, movies, sexual identity, control, and much, much more. The primary metaphoric vehicle is a mysterious, slimy tunnel that leads directly from a small door in an obsolete office building into the consciousness of actor John Malkovich. After fifteen minutes spent in Malkovich’s head, however, tunnel travelers are interdimensionally chucked out onto the shoulder of the New Jersey Turnpike, but the orgasmic thrill of living inside Malkovich’s skull (and what we see of that experience is, not incidentally, less than thrilling) spurs the characters (including office clerk and formerly unemployed puppeteer John Cusack, his frumpy—yes, frumpy—wife, Cameron Diaz, and sultry business chick Catherine Keener) to repeat the experience and steer Malkovich’s actions into fulfilling their sexual fantasies. Plenty of sequences suggest a consciousness on a chemical ride: a pet chimpanzee flashes back to his own orphanhood in the jungle; Charlie Sheen shows up (as himself), blabbering on about “hot lesbian witches!”; and then there’s the climactic homicidal chase through Malkovich’s tortured subconscious.

Pieces of April (2003)

Black sheep April (Katie Holmes, in her pre-Tom Cruise paparazzi days) tries to put together a Thanksgiving dinner for her suburban family in her teeny, rundown NYC apartment but her broken oven sends her on a desperate journey through the apartment building to find a neighbor willing to cook it for her. Meanwhile, her family sets out for the big city, along the way revealing their dysfunction with each other and with April. Sounds like a black comedy but Patricia Clarkson touches the perfect notes of pathos as April’s cancer-ridden mother. At this point in her career, Katie Holmes still showed so much promise. If you either have a black sheep in your family or are the black sheep, this movie may remind you of your own Thanksgiving past.

The Ref (1994)

Another great anti-Christmas Christmas comedy, wherein a burglar (Denis Leary) who busts into an upper-class, Noel-ed-up home and ties up its squabbling inhabitants (Kevin Spacey and Judy Davis) is the most sympathetic person in sight. He even gets to lay out the Man: “Great. I just beat up Santa Claus.” Not a movie for kids, nor is it for kid-swaddled, holiday-impassioned parents, but the rest of you can have a ball.