The last time writer and director Leslye Headland premiered a film at Sundance, it was 2012’s “Bachelorette,” a raunchy twist on the “girls just wanna have fun” subgenre of comedy, and one that might have arrived just a touch too soon after the box office juggernaut that was “Bridesmaids” (in a strange twist, Paul Feig’s feel-good comedy hit was nominated for two Oscars the morning after “Bachelorette” premiered at the festival). Headland adapted that feature from her own dark comedic play of the same name, and the results were decidedly mixed. A pitch black comedy with a winning cast of stars who were all saddled with despicable characters that repulsed each other (and their audience) at every possible turn. Fortunately, Headland doesn’t seem compelled to return to that kind of material, as the filmmaker has now made a refreshingly funny and romantic feature that is more than worth falling in love with (again and again).
Headland’s latest outing, the very amusing and genuinely sweet “Sleeping With Other People,” turns down the raunch levels just enough to allow actual affection to enter the equation. Still, this is a Headland feature, so mixed in with big romantic gestures are a bevy of bad behaviors, from drug-fueled children's birthday parties, to brunch-set brawls, and even a masturbation lesson that involves violating an empty bottle of green tea. Headland herself has described the film as “ ‘When Harry Met Sally’ for assholes.” The assholes in question here – Alison Brie as Lainey, and Jason Sudeikis as Jake – are so relentlessly appealing and well matched that their bad decisions and bad attitudes almost don’t matter, and by the time they do, the pair have actually come to terms with their wild ways.
Lainey and Jake first meet as somewhat innocent college students – Brie and Sudeikis play their younger versions in winking fashion – when Lainey sets about breaking down the door of a TA she is head-over-heels in love with (he will be the specter that looms over this entire feature) and who refuses to take her virginity. Manic and maddening, Jake comes to her rescue, and the pair eventually fesses up to their shared v-card-carrying status and lose it to each other. Twelve years later, neither of them have been able to forge a positive romantic relationship with another person (Lainey is still obsessed with Matthew, that damn TA, played by a creepily mustachioed Adam Scott, the lone one-dimensional character in the film, while Jake is just a womanizer), so when they run into each other at a sex addict meeting, it seems like fate.
It’s not. Headland doesn’t entirely subvert the romantic comedy genre here, but she certainly has fun twisting up some of its most obvious tropes for a little added pizzazz and some major laughs. Early in the film, Jake runs after a fleeing damsel in the rain, yet it’s not because he’s desperate to profess his undying love. He’s simply desperate to get her back into bed. By apologizing. For sleeping with her best friend. Later in the feature, Lainey herself hoofs it, chasing after Matthew when she unexpectedly runs into him while he’s out jogging. As he literally flees from her – though he is unaware of her presence – she struggles to catch him until she collapses into a heavy-breathing panic attack that has as much to do with her runaway emotions as it does her inability to run in street clothes. Headland doesn’t play these tricks up too often, however, and it’s a relief that no one ever feels the need to stop someone from getting on an airplane in some last ditch effort to prove their love (sorry, “Love, Actually,” but come on). Similarly, Headland doesn’t take her leads in the obvious direction once they’re reunited outside a church filled with sex-crazed perverts. Instead, the pair decide to try out friendship, and while the ultimate result is expected, the execution of Headland’s story is surprisingly rendered, both funny and sweet, sad and heartbreaking. Consider this one a rom-dramedy (and one for the ages at that).
The key here is Brie and Sudeikis, who exhibit the kind of cinematic chemistry that the recently ailing rom-com genre has been lacking for entire years. They’re not just good together, they’re believable, sexy, funny and sweet, and more than a little sad. It’s impossible to not want to watch these two people fall in love on screen – and they do, though Headland takes her offbeat romance in some suitably unexpected directions, while wisely playing up both Sudeikis’ cocky persona and Brie’s ability to look sweet even when she’s doing something horrible.
The film is Headland’s most commercially appealing directorial outing to date – emphasis on the “appealing” – and although there are a handful of missteps (it suffers from “too many endings” disease, and a subplot involving Jake seducing his own boss plays a bit too uncomfortably with power dynamics), “Sleeping With Other People” is ultimately a satisfying charmer with a big payoff. Hollywood is desperately in need of fresh, funny romantic comedies, and if Headland wants to be the filmmaker to fill that gap, we’ll follow her wherever she goes (though, perhaps not through an airport. That’s been done before). [B+]