The generally winning, big-hearted Steve Carell vehicle The 40-Year-Old Virgin is funny and realistically romantic, but almost never at the same time. It's essentially two movies operating at cross purposes. One's a raunchy, cartoonish Anchorman-like stoner comedy about a goofy-but-kind 40-year-old virgin (Carell) and his slacker buddies' fumbling attempts to get him laid. The other is a refreshingly adult but decidedly unfunny middle-aged romance about the fumbling courtship between a naïve hero with too little experience and a frustrated single mother/entrepreneur (Catherine Keener) struggling to raise a rebellious teenage daughter in a permissive society. The level of sensitivity and tact granted to the romantic side would draw sneers from the irreverent comedy side, and only the skill and charm of Carell and his supporting players keeps the clashing films from defeating each other entirely.
Making a surprisingly graceful transition to a leading-man role, Carell stars as a middle-aged L.A. electronics-store employee whose action figure-filled apartment helps explain why he's managed to put off sex for so long. At least one of his buddies/co-workers suspects that behind his creepily nice façade lurks a serial killer, but after news of Carell's sexual inexperience slips out, his co-workers set about helping him lose his virginity. Meanwhile, Carell begins an intentionally platonic romance with Keener that sets him stumbling onto the path of emotional maturity.
Like Anchorman (which co-starred Carell, and was produced by Virgin director/co-writer Judd Apatow) The 40-Year-Old Virgin has a ramshackle, episodic, seemingly improvised, boys'-night-out quality that succeeds largely on the strength of its cast's chemistry and comic chops. Sequences like Carell's would-be one-night stand with a drunk woman, or a bit with a buddy who advises him that the key to picking up women is acting like David Caruso in Jade—jerky and inquisitive—announce themselves as such self-contained comic units that they might as well be bookended by commercials. Nevertheless, The 40-Year-Old Virgin is often outright hilarious when it's not being all heartfelt and sensitive, as it mostly is during its second hour, when the shenanigans subside and the romance takes over. Though its title suggests a one-joke premise, Carell instills a good deal of complexity and sophistication into his affectionate characterization. Apatow genuinely loves his hero, and the film's innate sweetness carries it through the rough patches of a funny comedy with a central relationship that isn't particularly funny.