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The Life of the Pity Party

Jennifer Aniston’s strange run as America’s favorite spinster next door.

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Illustration by Kelsey Dake  

When Jennifer Aniston separated from Brad Pitt in 2005, US Weekly rushed out a mass-market paperback about the couple’s divorce titled Brad & Jen: The Rise and Fall of Hollywood’s Golden Couple. (Sample chapter title: “The Split Heard ’Round the World.”) It set the tone for the tabloid coverage of the only role she would play for the next seven years, a seemingly ceaseless stream of stories with headlines like OBSESSED WITH ANGIE!, I CAN’T STOP LOVING BRAD!, and JEN’S HEARTBREAK: DUMPED! Aniston appeared in more than a dozen movies during this period and added to the fortune she made on Friends, making an estimated $24.5 million in 2010 alone, according to Vanity Fair. She dated several handsome, notably tall actors and musicians—Vince Vaughn, John Mayer, Bradley Cooper—and, it seems safe to assume, had all sorts of expensive fun with them. But right until the news broke last week of her engagement to Justin Theroux, the celebrity-watching public knew her mostly as Sad Jen.

Cynics have suggested that Aniston played up her victimization, but aside from one ill-advised Vanity Fair interview (“Am I lonely? Yes. Am I upset? Yes. Am I confused? Yes…”), there’s little to substantiate the charge. If anything, what Aniston was a victim of was bad timing. She had the misfortune to have Pitt leaving her for Angelina Jolie just as celebrity journalism was metastasizing. With stars’ every movement fair game for the paparazzi, every image could in turn feed the master narrative: She wasn’t looking glum in that photo of her leaving a yoga class because she’d just been photographed against her wishes while makeup-less and sweaty; it was because she was realizing she was unlovable. It matters, too, that the post-Brad interregnum began as blogs were discovering that online, snark sells. Web archives can be spotty, but I swear I recall one blogger calling her “Eeyore,” the girl-next-door cover girl reduced to dysthymic donkey.

Then there was Aniston’s age at the time of the breakup. By dumping her at 35, Pitt had, through the tabloid lens, robbed her of the thing she surely wanted, the thing every All-American woman wants: children. She was an earlier iteration of the woman who can’t, it turns out, have it all, missing out on her prime mothering years while building a home with a man who then abandoned her for an exotic seductress who had once worn a vial of her former beau’s blood around her neck—an irresistible horror story. As the Brangelina brood grew to Brady Bunch proportions, Sad Jen was relegated to the realm of mopey spinsterdom.

At it happens, the demise of Sad Jen (or, at least, the evolution into Jen Who Has a Fiancé Now But Is Probably Still Empty Inside Because She Doesn’t Have Babies, Poor Thing) is timed nicely to coincide with the next generation’s celebrity cuckold: Robert Pattinson, whose high-profile split from vamp-harlot Kristen Stewart seems primed to create a new sad tabloid icon. Running with the part, he drowned his sorrows in a pint of ice cream served up by Jon Stewart. The only question is whether Sad Rob will sell as well as Sad Jen did.

Have good intel? Send tips to intel@nymag.com.


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