(1994) "What are we going to do now?" asks valedictorian Lelaina Pierce (Winona Ryder), who can't define "irony" and struggles with simply arithmetic, during the commencement address at her college in Houston.
Soon after, her closest friend, Troy Dyer (Ethan Hawke), "master of the art of time suckage," gets fired from his twelfth job (working at a newsstand where he copped a Snickers bar) and needs a place to crash for a few weeks. "Welcome to the Maxi Pad," says Lelaina's housemate, Vickie Miner (Janeane Garfalo), who works at the Gap and gets promoted to manager.
Keeping an account book of all the guys with whom she's gone to bed, Vick visits a clinic to be tested for HIV when one of her friends says he has AIDS. A fourth pal, Sammy Gray (Steve Zahn), rehearses with Lelaina how to break the news to his parents that he's gay.
Employed as an intern doing research and composing questions about the guests appearing on Good Morning, Grant!, a TV show, whose host, Grant Gubler (John Mahoney), dislikes her, Lelaina has been recording a documentary of her three friends and herself on videotape.
If I'd married right out of college and had kids, I might have been one of the parents of these Gen-Xers. Troy's folks split up when he was five; his dad has prostate cancer. Lelaina's parents both remarried after their divorce when she was fourteen; her dad (Joe Don Baker) gives her an old BMW with a gas card for graduation, even though she rejected BMWs in her speech. Suspecting she was conceived on an acid trip, Vickie says her mom and dad have been together for 26 years and act like brother and sister, which is why she doesn't intend ever to wed.
This cruel-world comedy, with numerous television references and musical selections (good soundtrack), was Ben Stiller's directorial debut in which he also plays the part of Michael Grates, a VP of programming for In Your Face TV, who accidentally makes Lelaina's acquaintance following an automobile collision.
On their first date he says he's non-materialistic and a "non-practicing Jew," to which Lelaina replies: "I'm a non-practicing virgin." They both share a love for astronomy, but in college the math got in the way of just looking up at the stars. No one needs college to gaze at the sky.
"You and me," says Troy, the philosopher/singer in a band who requires a high-IQ prerequisite for familiarity (which Michael fails), to Lelaina: five bucks, conversation, and smokes. They smoke too many cigarettes. Troy asks her why she acts like a jealous girlfriend; she accuses him of fondling the TV remote control ("sex is the quickest way to ruin a friendship," Vicky reminds her).
After she loses her job, Lelaina's father informs her that her generation lacks a work ethic, so she shows him. Why can't things return to normal like at the end of The Brady Bunch, Lelaina wants to know. (Because, Troy reminds her, Mr Brady died of AIDS.)
These kids were coming of age and struggling with the advantages of education and relative wealth during the Clinton administration when the US was experiencing its most prosperous period in recent memory. Lelaina's second question in her valedictorian address now applies to her generation as parents as well: "How can we repair all the damage we've inherited?"
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