Considering Judd Apatow’s humor is largely a product of his (and his friends’) own experiences facing life milestones (a motif apparent even in his films’ titles), it’s a germane moment to re-examine Apatow’s own career trajectory of the past decade. This is especially pertinent in light of the imminent release of This Is 40, whose protagonists (Pete and Debbie, played by Paul Rudd and Leslie Mann) were first featured in Knocked Up. It’s been five years since Apatow’s odd-couple stoner pregnancy comedy made critical waves, but in its wake the world of comedy (both film and television) has changed fairly significantly, particularly in the realm of gender representation. Female comediennes including Tina Fey, Amy Poehler, Kristen Wiig and Lena Dunham have started to break through the gendered glass ceiling of film/television comedy, particularly in writing, producing and directing credits. The bromance isn’t exactly dead, but in a post-“Girls” world — where female characters harbor most of the empathy and laughs and where male characters can still be written with depth, even by a girl — films like The Wedding Crashers and Knocked Up can seem downright outdated only half a decade later.

In 2007, however, Apatow was only starting to pave his path as a comedy brand, and Knocked Up was considered a sophisticated rom-com about an unlikely scenario: middle-class pregnancy (with barely a mention of the word abortion). The film’s praise was tempered, however, by a backlash of accusations of sexism by critics, compounded further upon Katherine Heigl’s own public admissions of the sexist portrayal of her character. Certainly, the film plays up the affable teddy bear qualities of male lead Ben Stone (Seth Rogen) to the umpteenth degree — Rogen has rarely been as charming — while the female lead Alison Scott (a bewildered and mostly silent Heigl) is depicted as either boringly tolerant, snooty, hormonally hysterical, or unimpressed by Ben. The film is about the difficulty of an unexpected pregnancy in today’s day and age, when most adults choose to hold off child-rearing until their 30s (or later), when they’ve settled down and reached a certain degree of financial security. In the case of Ben, the major obstacle to being a good father is the basic building blocks of adulthood, i.e. moving on from frat-boy collegiate life and keeping a steady job. In the case of Alison, her burgeoning career as an entertainment reporter doesn’t bode well for simultaneous mamahood. Certainly, the film has tapped into the twenty-first-century version of the modern work-life imbalance that didn’t really exist only a few decades ago–the idea that a woman can easily choose to prioritize her career over motherhood, and that men aren’t always bread-winning heroes.

But the film proposes instead gender dynamics that are not really that subversive at all, and in fact quite stereotypical: stunted emotional growth in adulthood is strictly a male phenomenon, women are inherently expert planners and quite OCD about the nitty gritty details of pregnancy; also, men will escape their family life through any means possible — be it fantasy baseball leagues — while women only get to whine and nag about wanting to get away from it all. Apatow decried Heigl’s use of the archaic word ‘shrew’ in reference to her character, but shrew — a word that’s used much more frequently to describe Leslie Mann’s Debbie by more critics than Apatow is aware of — is the perfect description of Apatow’s typical female character. It’s the stereotypical nagging wife that never lets the stereotypical goofy husband have fun that we’ve come to know all too well in sitcoms like “Everybody Loves Raymond” and “King of Queens.” Knocked Up would have been less problematic if the film had given Alison less screen time, and focused solely on the trials and tribulations of Ben, but its inclusion of Alison’s career as a burden to her pregnancy gives the impression that the film is supposed to be a gender-even comedy, depicting slackers and Type-A personalities at their most and least lovable. Ben is given plenty of moments for redemption despite his inability to get through his pile of pregnancy books, in addition to his moments of humor in the frat-pack scenes, whereas Alison mostly nods or looks like a deer caught in headlights when she’s being told what to do at work (lose weight in preparation for her new gig) or being offended by Ben’s lack of ambition. It’s unsurprising Heigl had a hard time playing a character who only really comes to life when there is abundant estrogen surging through her system; in order to be even remotely relatable, Alison must be hormonally hysterical.

While Apatovian gender politics are typically questionable in his own works, one thing his films usually get right is being resolutely funny (if not consistently, then at least intermittently) and most are considered critical and commercial successes (the exception, ironically, being the incredibly underrated Funny People). His films also share a trademark quality of unevenness, containing as many cracks and fissures as moments of genius, with none ever reaching the critical zenith of the cult classic “Freaks and Geeks.” This was apparent even in Apatow’s breakout hit The 40-Year-Old Virgin, though it was mostly saved by Steve Carell’s earnest performance. Where Virgin treated the man-child narrative as an endearing, if pitiable lifestyle borne from Carell’s adolescent fear of rejection, the man children of Knocked Up — Apatow’s next-gen frat pack that includes Rogen, Jason Segel, Jay Baruchel, Martin Starr and Jonah Hill — function mostly as vaudeville entertainers brightening up the audience during nonexistent intermissions. It’s difficult to determine if the purpose of Ben’s friends in the film is to depict real characters or simply explain his origins as a loser, though the former seems increasingly unlikely as the film progresses. These pothead slackers are masters of their own domain, perpetually lost souls nevertheless comfortable in their slackerdom, setting boxer mitts on fire and break-dancing in the early hours of the morn. Their scenes are admittedly hilarious on their own because the boys are given the spotlight to improvise jokes about genitals, weed and Starr’s bet beard–but it’s at the expense of a structurally-sound film. When it comes to basic film form, Knocked Up operates like two completely separate movies sewn together–a stoner bromance comedy that plays up the improvisatory skill-set of its riffing raff, and a rom-com about unexpected pregnancy that is more serious than funny. The ever-restless tonal shifts in the film are more unexpected than the pregnancy at the heart of the narrative–on the one hand, it’s easy to see why Apatow loves his new-gen comedy group and wants to highlight their chemistry onscreen; on the other hand, it simply doesn’t mesh with Alison and Debbie’s neurotic outbursts.

Apatow appears to be a huge believer in the adage “write what you know,” but he also has a predilection for collaboration, given his extensive filmography as a co-writer and co-producer. He also has a preternatural acumen in finding other talented creatives and helping them realize their own projects — some of whom, like Dunham, have had completely different life experiences. The film could have perhaps avoided its problematic gender representation and unevenness if Apatow had dragged in another story collaborator–most suitably, a strong female writer. It’s easy to say this in 2012. Five years after its release, Knocked Up now seems like a hopelessly outdated, lopsided affair; a representation of best/worst combos: its characters Ben and Alison, male and female gender stereotypes, and a weird, malapropos mishmash of the rom-com and bromance.

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