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How To Lose Friends & Alienate People

Sometimes, even The A.V. Club isn’t impervious to the sexy allure of ostensible cultural garbage. Which is why there’s I Watched This On Purpose, our feature exploring the impulse to spend time with trashy-looking yet in some way irresistible entertainments, playing the long odds in hopes of a real reward. And a good time.

Cultural infamy: After years of capping off at cult status, making silly movies and TV shows with his friends, Simon Pegg was poised, much like the “protagonist” of How To Lose Friends & Alienate People, to break into the big time. And on paper, this was the perfect vehicle: a film, based on the 2001 memoir of the same name, about trigger-happy fringe Brit journalist Toby Young, who winds up at the painfully mainstream Vanity Fair—losing friends, alienating people, blah blah blah. He’s Dwight Schrute without the beet farm, and his exploits hobnobbing with hoity-toity self-important starlets and journalists should have provided the film version with more than enough source material.

But screenwriter Peter Straughan and director Robert Weide kept only the main character’s rough trajectory and last name, then fictionalized just about everything else. (I haven’t read the book, but this is what I’ve gathered to be the case.) The film got a 35/100 on Metacritic (with the notable exception to the low scores provided by Roger Ebert, who claims this was “possibly the best movie that could be made about Toby Young that isn’t rated NC-17”), and a 37 percent rating on Rotten Tomatoes. Nathan Rabin in his D-grade A.V. Club review essentially says the film is lazy—it doesn’t know what to say, so it says nothing, in the least entertaining way possible.

Curiosity factor: But I don’t care much about what the above paragraph says. I think Simon Pegg is terrific—likeable, comically gifted, British. My first pass through Shaun Of The Dead a few years ago was, geez, just so much fun. So was Hot Fuzz. And Spaced. And Pegg knows what he’s doing outside the Edgar Wright/Nick Frost posse, too. His Scotty in the 2009’s Star Trek provided some needed shtick to the final scenes’ self-seriousness, and Run, Fatboy, Run proved Pegg’s comedic timing and sarcasm can withstand David Schwimmer’s laughter-devoid direction; without Pegg, the film would have been about as funny as Harry Potter And The Chamber Of Secrets. Also curious: this scene with Megan Fox.

Get this, her character hangs out with Pegg’s character, willingly, and he’s an entertainment journalist. Just like me!

The viewing experience: The first handful of scenes try oh-so-unsubtly to get us on Sidney Young’s side. (Sidney instead of Toby? What a stretch!) There’s a shot of a little boy staring at the TV screen, wondering how he’d ever get inside that TV and live where all the famous people live; then we cut right to where Young is rich and famous. And by rich and famous, I mean sitting next to Megan Fox at some awards ceremony, regaling us plebeians at home with a list of the impressive brand names adorning his person. (Before we even see Pegg, though, there’s this moment where the narrator says, “That’s me… wait, not that guy.” [Attractive man moves out of the shot.] “That’s me.” It’s at this moment that I know it’s time for the laughing.) And apparently, Fox’s character will sleep with him if she wins the award, which she does. “But I didn’t used to be like this,” Pegg turns to say to the camera. Boom, and we’re off to… a start.

Turns out before Young was, well, whatever he is in that last scene, he was this desperate journalist who believes he needs to get behind Britain’s velvet ropes where the starlets are waiting to tell him all about the blow they blow into their blow-holes. So he employs a variety of tactics—I don’t want to spoil anything, but there’s a pig, a wig, and a fake mustache, pig pee, the girl from Run, Fatboy, Run, and a bellboy who hears squealing inside a hotel room and continues knocking. Dude, if the room’s a-squealin’, don’t bother feelin’ (the door with your knuckles in a knocking fashion). Also, in spite of what you might think, given the previous scene, Young doesn’t operate totally solo; his Postmodern Review operation “employs” enough people to take over his entire living room—a bunch of quibbling loudmouths, including one whose only qualification is the fact that he owns a fax machine.

Thus when the editor of Sharps Magazine (it’s no Vanity Fair), played by Jeff Bridges, calls to woo Young to New York—turns out he’s been following Young’s saber-tooth satire for a while—the movie becomes elated. Elated enough for a cab ride that, for some reason, drives through the best, then the worst areas of New York one right after the other? The answer is yes.

Now, finally, comes the part of the movie where Young starts losing some friends and alienating some motherfuckers. After a night of dancing in a crowd of ladies, dissipating said crowd, and accidentally bringing home a chick with a dick (wait for it), Young heads into work smugly wearing a red T-shirt emblazoned with the words “Young, Dumb, And Full Of Come.” He got one for his new boss, who’s wearing a suit. Strike one. He finds an old photo and asks after the identity of the picture’s “Mussolini.” (It’s the magazine’s owner.) He adds “That funny-looking kid, is that his son?” (It’s his daughter, who happens to be the wife of his new boss.) Oof. He’s given the task of captioning some photos of a Chris Blick gallery opening (very famous), and calls to ask if Chris Blick is a man or a woman, wonky eye or no wonky eye. Should have checked the Internet. Strike three, he’s out?

Well, Young’s exploits can barely be called exploits, as they’re more like a series of minor annoyances, strung together to resemble a plot. Young doesn’t know who some young hotshot director is; he pitches a dumb idea in an all-staff meeting, a profile on Paris Hilton written tongue-in-cheek like she’s this undiscovered gem (priceless!); he finally snags an interview, with some actor doing an animated children’s movie, and asks him if he’s Jewish. These are the kinds of things that immediately make him an outcast to every single person he comes in contact with, and these things aren’t so bad. It’s almost like the film wants him to seem as buffoonish as possible, without all the actual buffoonery; wasn’t this supposed to be a movie about the most unlikeable person ever?

More than 90 percent of the film involves hedging its bets that viewers will turn against Young and storm out of the theater/their own homes in disgust. Which means the truly outrageous moments—the stuff that’s based a little more in the life of the real Young—stand out all the more. To wit:

Warning: this falls under the “things you can’t unsee” category. Also, it’s extremely not safe for work, unless you work somewhere where tranny-bits are commonly exposed:

(This in the biz is known as a “callback,” as well as the lowest point in Pegg’s career.)

So in order to super-promise-guarantee that audiences will go along for the ride, the film introduces a redemption story. See, entertainment journalists at Sharps are portrayed as party-hopping lothario-wannabes who pray their Blackberrys will one day light up to grant them publicists’ booty-call-like interview access. As an entertainment journalist, I can tell you all of it is true; why, just the other day, me and the boys of The A.V. Club put on our finest suits so we could go stand in line waiting for press credentials to an embarrassingly late Love Guru wrap party—if only we could get in! However, as the Jeff Bridges character points out, Young bitches about celebrity for the same reason Bridges used to bitch about celebrity: because they were invited to the party, and he was not. Well, once Young is at the party, it’s as good a time as any to abandon his integrity (in this movie, integrity = snark) and try to sleep with Megan Fox/watch a “steamy” montage.

Of course, it’s really easy to guess where the film is going to go with this one. Every part of How To Lose Friends & Alienate People feels like a manipulated exercise in exaggeration. The obvious question I had going in was how they’d go about making a movie about this terrible, just awful person. The answer is, they didn’t.

(REALLY IMPORTANT NOTE: I almost forgot about Kirsten Dunst. She’s in it too.)

How much of the experience wasn’t a total waste of time? 33.33 percent. Shenanigans not very shenaniganny; storyline too dry to be of much entertainment value. But there’s a comic ease with which Pegg does everything, including grabbing a fistful of tranny dick. I just couldn’t look away.