How to Lose Friends and Alienate People

In the late ’90s, a snarky British gossip rag journalist named Toby Young found himself working at Vanity Fair, mainly because its editor-in-chief, Graydon Carter, saw a lot of himself in the young man. What followed was a five-year tenure that could generously be described as disastrous, during which he wore inappropriate clothing, vomited on people, desperately tried to get any woman he could and sent a strippergram to work on Bring Your Daughter to Work Day.

Eventually Carter’s nostalgia gave way to the realization that he was paying someone who only typed 3,000 words over the course of years that managed to make it past the editors and censors, and sent Young back to England. Upon his return, Young penned the memoir sourced for the film. Indeed, many of the events of the book make it into the film, albeit toned down even for an “R” rating. The names have all been changed to protect identities, with even Toby being renamed Sidney, though you’d assume he’d have no problem with his identity being used.

He shows up at the office of Sharps editor Clayton Harding (Jeff Bridges) wearing a crude T-shirt and gets assigned to captioning photos — a necessity in a magazine, but hardly worth importing someone from England for. As the son of a baron (or lord, in the film version), Young has his credit cards printed with “Hon” for Honorable in front of his name to impress women, but can’t stop embarrassing himself long enough to ever mention it.

The more Sidney immerses himself into the celebrity scene (or tries to, at least), the more he learns the sordid truth about the shallowness of its stars and the twisted relationship between their agents and the magazines. The big publicist is Eleanor Johnson (Gillian Anderson), who ensures all her clients get positive print from Sharps. Young rebels at the notion of pampering a host of untalented celebrities and ends up annoying everyone from Harding to his immediate supervisor, Allison (Kirsten Dunst).

The problem with the transition is that Sidney loses his teeth. Played by the lovely Simon Pegg in the latest of his woeful miscasts in American films, he comes off as a charmer who nobly takes a stand against bowing to the demands of Eleanor, but makes nothing but mistakes. He often spits food on the rich and famous inadvertently, gets slapped a lot and even accidentally kills a dog.

In real life, Toby Young displayed the classic stalker mentality of desperately wanting to be in the limelight of the famous and to simultaneously tear it down. The more he discovered about the vapidity of the celebrity scene, the more he placed himself into a level of post-irony normally reserved for Andy Kaufman, self-destructing in some poorly thought out scheme of revolution.

Here, he’s simply an inept fool. The best and only glimpse we get of Young’s style in the film comes when he chats with an pretentious, overrated, Tarantino-ripoff director and cheerfully insists that “Con Air” is the greatest film of all time to get a rise out of him. The most infuriating thing about this adaptation is that moments like these are cast aside in favor of the lame insertion of a hackneyed love story.

The only friend Young has is Allison, but he longs for the beautiful, but vacant Sophie Maes (Megan Fox). I never really understood the fuss over Fox, as, depending on the camera angle in “Transformers,” she looked different and strange. If I learned nothing else from this film (and I didn’t), it’s that Michael Bay truly is a terrible director, because she actually looks like a human here. She also turns in a surprisingly solid comedic performance and holds her own against Pegg, albeit only because the film so thoroughly neuters him.

Of course, he eventually realizes who’s really stuck by him; yadda yadda yadda, you know how it will end, and it derails what was meant to be a scathing indictment of tabloid/fashion/pop culture journalism on a level “The Devil Wears Prada” does not even begin to approach. The acting is uniformly excellent, except for Dunst, who is at her usual loathsome “abilities.” Even Pegg gets laughs despite being far too charming to play Young.

However, in cutting down Toby’s exploits to ensure at least some teenagers could get in, it also removes the bile, and indeed the humor, from the story. What we’re left with is a clumsy, by-the-numbers romantic comedy with only occasional flashes of journalistic satire. Actually, it seeks to be a comedic parody of Federico Fellini's masterpiece La Dolce Vita; at one point Allison even cites it as her favorite film, and the finale takes place at a lawn screening of the classic. Yes, it's that kind of film.