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Representing New York naturalism and L.A. contrivance, respectively, The Squid and the Whale and The Dying Gaul are not exactly of a piece. The two films do share a theme (the end of a marriage), an on-screen profession (writing), and a composer (Steve Reich), and feature equally inscrutable titles. Yet their tones could hardly be more divergent if the first movie really were a nature documentary and the second actually a costume epic set during Caesar’s conquest of France.

The fourth and best film by second-generation Brooklyn boho Noah Baumbach, The Squid and the Whale is partially autobiographical, and it seems as uncensored and intimate as entries from someone’s diary. Indeed, this squirmily hilarious study of a dual-Ph.D. family feels so anecdotal that its careful structure is not immediately obvious. Yet the writer-director, whose previous efforts include Kicking and Screaming and Mr. Jealousy, knows exactly what he’s doing. The action begins on an interior tennis court, in or near Park Slope, where 16-year-old protagonist Walt Berkman (Jesse Eisenberg) is about to begin a doubles match with younger brother Frank (Owen Kline) and their parents, Bernard (Jeff Daniels) and Joan (Laura Linney). “Mom and me versus you and Dad,” announces Frank, and that’s exactly how the story proceeds.

An author and literature professor, Bernard has lost none of his presumption as the acclaim for his novels has waned. He knows which books, films, and tennis players are genuine and which are not, and his highest compliments are such words as “dense” and “risky.” Walt follows this example, often recycling or mangling his dad’s judgments, as when he proclaims A Tale of Two Cities “minor Dickens” or The Metamorphosis “very Kafkaesque.” Taking the quick path to authorship, he decides that he wrote Pink Floyd’s “Hey You” and plays it for his impressed family. Then his parents announce what is supposed to be a dignified, amiable divorce, with an every-other-night commitment to joint custody, and the boys choose sides just as Frank said. Before long, Walt is calling his mother “whore.”

This is a withering self-portrait, as well as a forthright account of some minor New York celebs. (Baumbach’s father is a novelist, his mother a former Village Voice film critic.) While the details are reportedly not drawn from life, the emotions seem entirely true. The easygoing but self-centered Joan proves remarkably capable of simply continuing her life, beginning a successful journalism career and an affair with an unintellectual tennis pro (Billy Baldwin). Across Prospect Park in an “elegant” new home that’s actually a wreck, Bernard seethes, bitches, and counts every penny. His life becomes even more complicated when he unwisely allows the sexiest of his students, Lili (Anna Paquin), to move into a spare room. A more capricious cutie than the similar Katie Holmes character in Wonder Boys, Lili flirts with both Bernard and Walt, leading the latter to downgrade his provisional same-age girlfriend (Halley Feiffer). Meanwhile, the largely unsupervised Frank discovers alcohol and masturbation—and can’t keep these breakthroughs to himself.

Named for a diorama at Manhattan’s American Museum of Natural History, The Squid and the Whale is not a great-looking movie. But it does boast Baumbach’s best script to date, which offers a suitably jaundiced insider’s view of ’80s New York highbrows. (After the divorce, the only household valuables the grown-ups attempt to hide from each other are their books.) That the director is well-connected is revealed by the cast, which includes the son of Kevin Kline and Phoebe Cates and the daughter of cartoonist and writer Jules Feiffer, as well an impeccable selection of “downtown” rock and minimalism, including the Feelies, Lou Reed, Dean Wareham and Britta Phillips, and Reich’s Music for 18 Musicians. Baumbach’s not showing off, though. This is just his world.

He understands that world well enough to recognize its absurdity, in a realization that presents the key to appreciating the movie: It’s OK to laugh. With all the anguish, humiliation, and seeming revelations on the screen, some viewers watch in stunned silence. But the events that inspired the screenplay transpired 20 years ago, and Baumbach has had time to fathom their silliness. Aided by Eisenberg’s earnestness, Linney’s distance, and Daniels’ vanity-free embodiment of an educated buffoon, the director locates an equal measure of humor and horror in such everyday remarks as “I’m taking the cat.” As droll as it is pitiless, The Squid and the Whale can be paid the ultimate compliments: It’s dense, risky, and very Baumbachesque.

The directorial debut of playwright and screenwriter Craig Lucas, The Dying Gaul is a slick, Hollywood-style vehicle powered by anti-establishment anger. The filmmaker’s rage at the cost of AIDS and at a U.S. government he has called “barbarian” slops onto his characters, scarring their lives like acid. All three of the principals do bad things, but the punishment Lucas metes out to them goes far beyond justice, all the way to melodrama.

It’s 1995 when abrupt, apparently superficial studio executive Jeffrey Tishop (Campbell Scott) reads a script he thinks could be the next Terms of Endearment. The proposed movie is titled The Dying Gaul, a reference to a classical sculpture of a mortally wounded warrior. Jeffrey offers writer Robert Sandrich (Peter Sarsgaard) $1 million for the screenplay, on one condition: The story, which was inspired by the AIDS death of Robert’s male lover, must be rewritten as a heterosexual romance. Jeffrey’s interest in the project is seconded by his empathetic wife, Elaine Tishop (Patricia Clarkson), a political activist and former screenwriter who finds Robert’s tale profoundly moving.

Elaine and Robert become friends, and the impoverished author, who initially rejects the $1 million, is tantalized by the Tishops’ upscale oceanfront lifestyle. He’s also seduced by Jeffrey, who is secretly bisexual. The studio boss is a walking metaphor for the hypocrisy of America and its movies; he insists that love between two men is unsalable even as he’s enticing Robert with such porn-flick lines as “I want you inside me.”

When Elaine learns that Robert slakes his despair and lust by trolling gay-sex chat rooms, she assumes a male identity and logs on. Soon she’s posing as Robert’s deceased lover, halfway convincing the bereft writer (who’s a Buddhist, for what that’s worth) that she really is the dead man. Over the course of their conversations—awkwardly recited by the actors in voice-over as they type—Elaine realizes that her husband and Robert are having an affair; the result is a very Victorian denouement. Innocents are destroyed by Jeffrey’s deceit—which must be another metaphor.

Ascending from writer to director—and transforming his original play into a film—Lucas works too hard to prove he knows how to make an image. The surfaces glisten, the camera is always moving, and oblique angles and flashy framing devices distract from the action. So does the score, which uses chunks of several Steve Reich compositions, most conspicuously Drumming and Proverb. The resulting movie is overly fussy, and all the cinematic ornamentation doesn’t prevent it from being stagey and didactic. The Dying Gaul treats the 1990s as an exotic period in American history, and even if some of the plot twists and characterizations suggest the 1890s instead, this is a parable from a place or time that’s strangely implausible.

The actors do their utmost to pretend otherwise. The star of a previous Lucas-scripted film, Alan Rudolph’s The Secret Lives of Dentists, Scott shows absolute commitment to the writer-director’s vision. Sarsgaard, who’s developed quite a portfolio of homoerotic supporting roles—just look at this week’s Jarhead—is equally fervent, and Clarkson does what she can with a character who, if not meant to be misogynistic, is certainly an outlandish example of the woman scorned. Even when taking her baroque revenge, however, Clarkson’s Elaine can’t be as hysterical as the film that contains her.CP