When wickedly funny Los Angeles playwright Leslye Headland first began taking meetings with Hollywood executives, she heard the same question on repeat: "They’d ask,‘What’s the female version of an Apatow movie?’ I would always say, 'Depressing.'" Audiences love a man-child, but would they find "a woman struggling with her femininity" just as funny? Turns out they do. Bachelorette, Headland’s raucous Sundance hit, in theaters this month, is hilarious, twisted, and startlingly incisive. On the eve of a wedding, three early-thirties bridesmaids lean hard into old archetypes—the ditz (Isla Fisher), the nympho (Lizzy Caplan), and the alpha female (Kirsten Dunst)—and wrestle with their own inadequacies as the rotund runt of their high school pack (the always-game Rebel Wilson) beats them all to the altar, with a Disney- perfect prince to boot. Make no mistake: This isn’t Bridesmaids. Headland spins her premise into something grittier, a fiercely sharp send-up of the idea, she says, "that there’s a checklist by which women should live their lives, so that they’re always defining themselves by what they don’t have."
Headland wrote and directed the film based on her 2009 Off- Broadway play of the same name, the second in a series she staged around the seven deadly sins. Bachelorette was her take on gluttony—on the modern fallacy that wholeness comes from having more, more, more. The opportunity to dive into such keen comic material enticed the indie’s starry cast. "There’s a Peter Pan generation of women who haven’t had to grow up, who feel like the world owes them something," Fisher says. "They’re rich and white and spoiled, and they expect everything while doing nothing. They’re the end of civilization, these women."
Dunst’s type-A Regan takes the biggest hit from her friend’s triumph but tries to keep it together with steely determination. (One of the film’s groomsmen lays it out: "You know how there are serial killers, and then there’s Hannibal Lecter? Well, there are women, and then there’s Regan.") Despite her best efforts, the brood goes on a blow-and-booze bender that makes The Hangover (a Headland favorite) look like a coolheaded search party. Along the way, the intricacies and endurance of female relationships perfectly unravel.
"Female friendships are deep and complex, and the lengthy ones are submerged in this dark history," says Caplan. "If you’ve been friends for 10 years, you’ve done some terrible shit to each other." Dunst concurs: "It’s the part of your friends you don’t want to see. That should be the tagline." Evidently, that’s just the part film festival crowds did want to see. "I was amazed when people came up to me to say they’d been there or that they got it," says Headland. "I thought, Oh, that’s awesome. I’m not alone!"