Written and directed by Judd Apatow

With Seth Rogen, Katherine Heigl, Paul Rudd, Leslie Mann, Jay Baruchel, Jonah Hill, Jason Segel, and Martin Starr

Judd Apatow is a man who plays well with others: he started out writing for Ben Stiller and Garry Shandling, went on to produce the two funniest Will Ferrell vehicles (Anchorman and Tallageda Nights), and is currently working on projects with Ferrell, Adam Sandler, Owen Wilson, writer-director Jake Kasdan, and the gifted Texas director David Gordon Green. But Apatow’s more personal projects–the cult TV series Freaks and Geeks and Undeclared, his sleeper hit The 40-Year-Old Virgin, and now the wonderful Knocked Up–have pulled away from the boys’ club of big gags and blatant stupidity, dealing honestly with lack of understanding between the sexes. In Apatow’s comedy boys and girls tend to view relationships as the gateway to adulthood, which leads to fears and disappointments as funny as they are painful.

A recent profile in the New York Times Magazine portrays Apatow as a careful student of comedy who audiotaped his favorite stand-ups off the television. He came of age in the late 70s and early 80s, when the comic vanguard was familial sketch-show ensembles like the brilliant SCTV crew and the first cast of Saturday Night Live, and he’s carried that dynamic into his own work, assembling a troupe of eccentric performers he’s called upon since he produced Freaks and Geeks in 1999. The Times piece, by Stephen Rodrick, details the impact his parents’ divorce had on him as a teenager and uncovers the tension in Apatow’s adult life between his real family (actress Leslie Mann and their two daughters, Maude and Iris) and the masculine camaraderie he enjoys with his collaborators. The creative partnerships come off as a kind of eternal youth, perpetually bumping up against his domestic responsibilities.

The logical starting point for any discussion of Apatow’s oeuvre is Freaks and Geeks, a wonderfully funny and honest hour-long high school sitcom set in the early 80s that wowed critics but was swiftly canceled by NBC. (The show was created by Paul Feig, but Apatow was greatly influential as a story editor and wrote and directed several episodes.) Apatow had learned from Shandling’s The Larry Sanders Show that the most penetrating comedy comes from a character’s weakness, and Freaks and Geeks was merciless in recalling the terror, humiliation, and disillusionment of crushes and dating. One of the main characters, geeky freshman Sam Weir, spends numerous episodes mooning over the virginal heartbreaker Cindy Sanders and hatching misguided romantic strategies with his clueless pals. But when Cindy actually ditches her jock boyfriend and goes out with Sam, his dream come true is tarnished by the discovery that she’s terminally boring. (What cinches it for him: she doesn’t like The Jerk.)

Apatow tried again with the Fox sitcom Undeclared, which was set in a coed college dorm and added sexual initiation to the list of teenage traumas. But it was severely constrained by its half-hour format, and like Freaks and Geeks it was canceled in a matter of months. Apatow didn’t get a chance to pursue his own ideas again until the success of Anchorman: The Legend of Ron Burgundy enabled him to make his feature directing debut, The 40-Year-Old Virgin (2005). Coming down the pike, Virgin looked like another lowbrow farce in the Ferrell/Sandler tradition, but there was something poignant about its story of a decent, middle-aged electronics salesman (Steve Carell) who’d never gotten around to having sex. Apatow managed to balance raucous laughs against the character’s halting, fretful romance with an offbeat single mother (Catherine Keener), and the combination made Virgin one of the best-loved movies of the year.

The story originated in a sketch Carell used to perform onstage, but Apatow clearly connected with the idea of a grown man still mystified by the opposite sex. Andy Stitzer, the title character, seems like one of the losers from Freaks and Geeks transported magically into middle age: his condo resembles a kid’s bedroom, the shelves lined with comic book, horror, and sci-fi memorabilia. Andy’s crude young pals at the electronics store are all sexually experienced, but in a way their perception of women is as infantile as his. Once they uncover his embarrassing secret, they launch a campaign to get him laid, which allows Apatow to roll out a seemingly endless series of dating nightmares. Yet in the end Andy becomes a man not by bedding a woman but by learning, against all odds, how to be honest with her.

The friction between men and women is even more pronounced in Knocked Up, the story of Ben, an unemployed slob (the superbly sarcastic Seth Rogen, who’s been working with Apatow since Freaks and Geeks), and Alison, a beautiful E! TV host (Katherine Heigl of Grey’s Anatomy), who share a drunken one-night stand and then struggle with Alison’s resulting pregnancy. Like Andy in The 40-Year-Old Virgin, Ben is living an abnormally prolonged childhood, paying his bills out of an accident settlement, blowing bongs all day, and scheming with his four rowdy roommates (Jonah Hill, Jay Baruchel of Undeclared, and Jason Segel and Martin Starr of Freaks and Geeks) to create a lucrative Web site that tracks nude scenes in movies. He and Alison are profoundly mismatched, yet they resolve to raise the baby together, which forces Ben to grow up as Alison’s belly grows out.

In Knocked Up, as in much of Apatow’s writing, men and women see their romantic partners as escorts into adult life, but in this case the pressures of parenthood make growing up a decidedly downbeat proposition. Alison’s half of the story is dominated by her sister, Debbie, whose unhappy marriage seems like a dire preview of Ben and Alison’s future. (Apatow has underlined the autobiographical element by casting his own wife as Debbie and his own scene-stealing daughters as her kids.) Debbie’s husband, Pete (played with sardonic precision by Paul Rudd), adores his children but laments his lack of freedom; manning a bubble machine as the girls squeal and play, he sadly remarks to Ben, “I wish I liked anything as much as my kids like bubbles.” Ben and Pete bond immediately, and the movie’s doubtful view of marriage is enhanced in the latter half by how naturally the couples split along gender lines.

Apatow ends the movie on a joyful note, but to his credit he never backs off from his dark view of Ben and Alison’s future. They’re radiant at the birth of their new child, yet still seem as burdened as Pete and Debbie. The only moment of genuine hope comes during the delivery, a howlingly funny climax that surpasses any such scene in American comedy. When Debbie arrives at the hospital, she tries to eject Ben from the delivery room, insisting that she’ll take care of her sister. To her surprise, Ben tells her off good, sends her out to the waiting room to sulk, and returns to Alison’s side where he belongs–for better and for worse, as they say.

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