"What a rapscallion," Robert Weide's film version of journalist Toby Young's memoir begs us to exclaim, as we follow Young's "fictionalized" self from London to New York, where he seeks to establish himself King Rake of the high-end pop journalism world. Vanity Fair served as the real Young's sounding board. There his insouciant musings and acid takedowns earned him a reputation, which in turn bought him access to the same elite restaurants and parties he'd been crashing since his no-name London days. After being booted from both magazine and industry after one stunt too many, Young wove his exploits into bestseller gold. The book begot a play, which begot this intermittently enjoyable but watery movie from Weide, director of a couple dozen Curb Your Enthusiams.
The movie settles into mediocrity straightaway, as a narrating Sidney Young tells of his early infatuation with celebrity over images of him as a child staring wide-eyed into the television's glow. Yes, staring wide-eyed into the television's glow. It's the most obvious move possible, right out of any Lorne Michaels production (missing only a descending crane shot from sun-dappled treetops). What follows is a series of misadventures and one-off gags highlighting Young's attempts to "mix things up" in the land of stodgy journos. Simon Pegg does all he can as this lightly glamorized Young; he's best in the quieter scenes, like those with his intellectual father and his misguided, sweet co-worker Alison (Kirsten Dunst).
It's the stunts that fizzle. Young errantly kills a starlet's dog, sends an inter-office tranny strippergram on bring-your-daughter day, and wears a Young, Dumb, and Full of Come t-shirt. It's fairly standard-issue impishness, but we're asked to view it as admirable defiance. When he champions Con Air to a group of snobbish gasbags at a party, it's a victory for high/low blindness to arbitrary notions of prestige and status. But then How to Lose is ever speedy to point out that Young is no mere trash culture muckabout. He empathizes with the obscure actress at the party, citing her best performances, to her blushing gratitude. When it's revealed that he holds a masters in philosophy, the news is supposed to be bracing. You mean, this clown?! When Young noshes a greasy burger in the elevator at Sharp's (the fake Vanity Fair), is he a slob out of water, or a reverse snob pseudo-slob in his natural environment? These are potentially thorny complexities made confusing by Weide's uninterested treatment. And as in Shattered Glass (the movie version of con journalist Stephen Glass's The Fabulist), you can't help but wonder which wild "mishaps" are self-conscious grabs for memoir material.
When How to Lose runs out of ideas, Weide cuts to shots of the rising star character played by Megan Fox, whose hyper-hotness is milked for all it's worth. Fox's tone deaf delivery is beside the point, but Jeff Bridges compensates as Sharp's editor-in-chief, a Graydon Carter lookalike with a flowing gray mane who constantly flips a matchbook and cigarette in his hand.
In the tradition of Bright Lights, Big City and The Devil Wears Prada, our hero rises in the ranks but inevitably loses his illusions. It's never clear how we're supposed to react as Young shelves his us-versus-them moral code and kisses ass in the quest for bylines, and the happy ending reunion between Young and Alison feels tacked-on and desperate. The movie seems to let down its source. Like Man on the Moon, it's an example of the failed tack of giving a subversive subject the middle-of-the-road treatment.