Media satire shows how to lose fans and alienate audiences

How to Lose Friends & Alienate People opens with a young man equating Hollywood to Shangri-La.

By Matt Zakosek

How to Lose Friends & Alienate People opens with a young man equating Hollywood to Shangri-La. It’s hardly an original thought, but then, not much in the movie is. A toothless publishing-industry satire that wastes its competent cast, Alienate may have fared better as a two-part episode of Ugly Betty.

Simon Pegg stars as Sidney Young (Toby Young in the book and in real life), a hapless schmuck who infiltrates the corridors of a high-profile glossy called Sharps. But the media-world observations in The Devil Wears Prada were sharper, and as editor-in-chief, Meryl Streep’s Miranda Priestly (thinly based on Vogue’s Anna Wintour) was more memorable than Jeff Bridges’s Clayton Harding (thinly based on Vanity Fair’s Graydon Carter).

This is not to imply that Alienate isn’t enjoyable—just inconsequential. The problem is that so many of Young’s actions strain credulity, even for this brand of broad comedy. Showing up to your first day at a new office in a shirt that says “Young, Dumb, and Full of Cum” is too much even for the gaffer on the new John Waters flick. Pretending you’re the handler of the star of Babe 3 so you can sneak past the velvet rope is kind of funny, but come on—even ten years later, everyone knows Babe: Pig in the City flopped. Why would a studio bankroll a sequel now?

Stale references like this abound in Alienate, which does boast one pretty funny running gag—a sadly plausible biopic called Mother Teresa: The Making of a Saint, starring the shallow young starlet Sophie Maes (Transformers’ Megan Fox). It would have fit right in the slew of fake trailers that open Tropic Thunder. And though featuring deceased director Anthony Minghella’s son Max as a spoiled young auteur was a stroke of casting genius, the rest of the line-up reads like a Who’s Who of Hollywood in the ’90s. Kirsten Dunst (who arguably had her best roles in that decade), Gillian Anderson, Jeff Bridges—are these really the famous faces the producers wanted for a supposedly au courant parody? Even Minghella’s Vincent Lepak is accused of “think cinema started with Tarantino,” which almost feels old-school at this point.

To be fair, Alienate may feel a little too ’90s because the memoir on which it is based happened in the ’90s. In a recent interview, Young admits, “I think it’s probably tougher to make it now than it was 13 years ago, particularly in the print media…. I probably wouldn’t be working for Vanity Fair, I’d probably be working as Nick Denton’s slave at Gawker and being paid nothing.” But if director Robert B. Weide is going for a period piece, the tone is wildly inconsistent, with all cocaine references hearkening back at least to the ’80s. And if Babe 2 was released in ’98, well, I haven’t had this much trouble keeping track of time since Memento.

In a case of life imitating art imitating life, Toby Young was strongly advised to keep away from the set after Dunst allegedly mistook his advice as a criticism of her acting ability. To his credit, Young is gracious in his account of the matter, citing the old Hollywood maxim that “being a writer on the set of your movie is like being a husband in a maternity ward”: essentially useless. (Besides, Young admits, he didn’t even write the movie.) But if Young had criticized Dunst’s performance, it wouldn’t be completely unwarranted; her ingenue character is indistinguishable, from Wimbledon to Wag the Dog to Eternal Sunshine of the Spotless Mind. She’s always playing bland, unobjectionable young women with vaguely troubling moral crises; in Alienate, the crisis is choosing lovable loser Sidney over her cad of a boyfriend. (The film keeps his identity under wraps until the second half, though you’ll have it figured out long before then.) She’s a talented actress, but isn’t it time for her to de-glam and sink her teeth into some choice Oscar bait?

But back to the Shangri-La delusion. A pivotal plot point involves Sidney’s mother’s career as a starlet. But if Sidney’s mom was a minor celebrity—with the endless striving and ass-kissing that entails—why would her son have an idealized impression of Hollywood at all? Wouldn’t he be familiar with callbacks and failed pilots and contentious relationships with agents? It’s not as if Young was some bit player, either; the sight of her in a lusciously shot black-and-white movie triggers an epiphany as Sidney channel-surfs in a hotel room.

At the Alienate screening, I was lucky enough to introduce myself to Roger Ebert, who was very gracious about my sycophantism (perhaps because it was in the spirit of the film we just watched). He couldn’t talk at the moment, but he nodded and gestured encouragingly as I rambled on about the Sun-Times. It was inspiring to witness a celebrity sharing his passion in spite of a recent setback—and a much more effective argument against Hollywood’s equivalence with Shangri-La.