Alison (Kirsten Dunst) is writing a novel. She’s writing it longhand, in a notebook she carries with her to bars and parks, a notebook that serves as an emblem of her authenticity, her resistance to the glib and glitzy world of New York City celebrities. Such resistance earns Alison high moral marks of course, especially as she is surrounded, in How to Lose Friends & Alienate People, by superficial, self-absorbed, and irritating personalities.
Alison is quite aware of her predicament, thank you. Hailing from Port Huron, she made her way to the big city hoping to make her artistic mark. So far, she’s still hoping—that her gig writing blurbs and fluff pieces for a glossy magazine called Sharps is just a step along the way to a goal, that her loneliness and frustration will eventually give way to full-on romance and joy. And really, she has every reason to hope, as she’s living inside a romantic comedy, as the proper object of affection for the hero. The trouble is, she has to wait for him to come to terms with his own trajectory and save her.
That rescuer is Sidney Young (Simon Pegg), recently arrived in the Big Apple from London. Based loosely on Toby Young’s unsurprising expose about his less-than-happy stint at Vanity Fair, Sidney’s story begins with an admission, that as a child, he imagined the entertainment industry as Shangri-la. As a young boy version of Sidney watches his own mother perform in a black-and-white movie romance on TV, he embodies an exceedingly perverse nostalgia, as he turns his dead mother into an ethereal sign of a world she never exactly inhabited. If this briefly noted backstory doesn’t quite explain the boy’s journey from fan to mud-slinging scribe, it supplies a rudimentary “psychology.” His subsequent bad behavior now has a point of departure.
As Sidney grows up to resent his mother’s absence and his philosopher father’s academic prowess, he buries himself in entertainment’s most noxious netherworld, the gossip-tabloid-parasite rags. He tells himself (and you) that his adversarial posture toward the industry makes him virtuous, announcing early his disdain for the “quid pro quo” between magazines and celebrities. Instead, he says, he wants to write “real” stories, taking aim at industry excesses and calling out the posers for what they are. His efforts are rendered in familiar slapsticky ways. At film’s start, Sidney dons a fake mustache and a waiter’s jacket to crash a party after the BAFTA awards in London. Here he corrals Thandie Newton, who politely half-listens to self-promoting drivel, and even laughs when he makes a decent joke. It’s a sweet moment that suggests: 1) Pegg and Newton, playing herself, have moved on from the disaster of Fat Boy, and 2) this new movie will manage some ironic self-awareness concerning its overbearing, much-too-easily-targeted milieu.
But no. the sweetness and the irony are promptly bulldozed by a bad joke featuring a peeing pig, whereupon Sidney is shuffled off to NYC. Hired at Sharps by silver-maned Clayton Harding (Jeff Bridges, with an obvious nod to VF‘s Graydon Carter), Sidney again vows to do right, at least when he’s challenged by Alison. They meet in a bar on his first night in town, where she’s writing in that notebook and he’s trying to pick up anyone with breasts.
Sidney’s quest initiates some unfunny compromising situations, one involving a transvestite (providing still more overkilled conventional comedy when Sidney gets a gander at her penis) and a few others a vacant starlet, Sophie (Megan Fox). Fond of her Chihuahua and speaking in breathy baby coos, Sophie is a device to push Sidney toward Alison.
As such, Sophie represents, rather incessantly, the industry Sidney purports to despise. She also occasions his encounters with a couple of gatekeepers: her agent, Eleanor (Gillian Anderson), and Sidney’s assignment editor, Lawrence (Danny Huston). Like flipsides of the same corporate coin, these two offer Sidney similar options: write the fluff piece in order to gain access, which translates into cover stories, faux clout and lots of money. It’s not long before Sidney has become exactly the whore he once derided, with an uptown apartment, presents from Ralph Lauren, and a different skinny girl every night. As you and Alison wait for Sidney to come around, How to Lose Friends loses its way.