Simon Pegg, the British actor who wrote and starred in the fiendishly clever “Shaun of the Dead” and “Hot Fuzz,” should not have been cast as the lead in “How to Lose Friends & Alienate People.” The character, a journalist named Sidney Young who comes to America to break into the magazine business, does abrasive and offensive things with an attitude of narcissistic obliviousness: I don’t know or care whether this will upset anyone, because I’m the only person who matters anyway. That doesn’t jibe with Pegg’s persona as a hapless, unassuming striver who wants to do the right thing but occasionally messes up. You always want to root for Simon Pegg, but Sidney Young deserves whatever he gets.
Sidney is the slightly fictionalized version of Toby Young, who wrote the memoir on which the film is based. In real life, he worked for Vanity Fair under Graydon Carter, whose work with the satirical Spy magazine Young had greatly admired years earlier. I haven’t read the memoir, but comparisons to “The Devil Wears Prada” don’t seem entirely unwarranted. Where that book and movie were about women and fashion, “How to Lose Friends” is about men and celebrities. And in the movie version, the names have been changed to protect the guilty.
In the beginning, Sidney is writing for a rabble-rousing, celebrity-skewering mag in London that runs cover stories such as “Posh Spice? Like F*** She Is!” and is always one step away from a libel suit. Sidney prides himself on sneaking into — and subsequently being thrown out of — fancy parties where celebrities are in attendance. His greatest pride is a photograph of himself being administered a headlock by Clint Eastwood.
The Graydon Carter/Vanity Fair character, now named Clayton Harding and editing something called Sharps magazine in New York City, sees some of his own youthful recklessness in Sidney and hires him to write for Sharps’ “I Spy” section. (“You photograph famous people when they’re drunk” is Sidney’s succinct and astute description of the feature.) Clayton, played by a long-haired Jeff Bridges, is too wealthy and powerful to be as iconoclastic as he once was, but he sees a chance to relive those glory days through Sidney.
Sidney is immediately bothered by the dirty behind-the-scenes machinations involved in producing a celebrities-and-culture magazine. A high-powered publicist named Eleanor Johnson (Gillian Anderson) wants Sidney to do a feature on up-and-coming starlet Sophie Maes (Megan Fox), but she wants complete editorial control over the piece, lest Sidney say anything remotely unflattering in it. Real journalists don’t let their subjects kibitz.
Meanwhile, Sidney is disgusted by the shmooziness of fellow writer Lawrence Maddox (Danny Huston). And since all main characters need a love interest, Sidney has Alison (Kirsten Dunst), a fellow “I Spy” reporter and a dreamy-eyed would-be novelist whose boyfriend doesn’t believe in her talents.
The film begins strongly enough, with Pegg’s quiet, deadpan sarcasm carrying the day, and the opening scenes of Sidney’s foolish attempts to break into star parties are encouraging. But as soon as he gets to New York the character becomes inconsistent and erratic. He’s proud of his paparazzi-level shenanigans (like the Eastwood headlock), but suddenly he’s judgmental about “photograph[ing] famous people when they’re drunk”? Suddenly he’s a real journalist with ethics when it comes to writing a fluffy celebrity profile? He’s oblivious one minute, aggressively pushy the next; shrewd and conniving here, full of integrity there. He can be cocky and arrogant in one scene, self-effacing in another.
Some of what Sidney does feels so outrageously out of line — like wearing a T-shirt with an unquestionably vulgar slogan on his first day of work — that you’d think he must be doing it on purpose. Yet he seems genuinely surprised when people are bothered. A Simon Pegg character would normally be too self-aware (and too self-doubting) for that to happen. This guy, this Sidney Young, I don’t know what his deal is.
“Curb Your Enthusiasm” director Robert Weide, working from a screenplay adaptation by Peter Straughan, finds his best moments in the periphery. Max Minghella has a terrific couple scenes as a pretentious young filmmaker (“I am my own role model”) desperately in need of humbling. (This would be more satisfying if the man to do it, Sidney, didn’t need to be taken down a couple pegs himself.) Gillian Anderson sinks her teeth into the no-nonsense publicist role, and Jeff Bridges brings some of his leftover burnt-out-hippie Lebowski vibe to Clayton Harding.
I continue to admire Pegg’s comic abilities, and he seems to have given it his earnest best here. He’s just not right for the part — and the story fizzles out halfway through anyway, when it becomes too focused on the Sidney/Alison relationship, which is never going to be plausible no matter how much time is spent on it. Like Sidney Young (and the memoirist behind him), Pegg has had trouble finding his niche in America. I just hope he doesn’t lose any more friends or alienate many more people before he does it.
C+ (1 hr., 50 min.; )