It’s hard to care too much about someone as obnoxious as Sidney Young, the main character of How to Lose Friends and Alienate People, played by Simon Pegg. Having a main character as unlikable as Sidney is one of the key things that doesn't work in it. There are some things that do work — a few funny bits, some great comedic performances — but they don't quite make up for the experience of watching the movie as a whole, which ends up being just kinda "meh."
The character of Sidney Young is based on the real Toby Young, who wrote the memoir on which this movie is based. In the film, Sidney is a cynical British writer who is obsessed with the notion of celebrity while simultaneously finding it ridiculous. He puts out a magazine in England called Post Modern Review, full of snarky pieces about famous people. Amused by this, Clayton Harding (Jeff Bridges), editor of Sharps magazine in New York offers Sidney a job and the bumbling, uncouth Sidney sets off for glamorous New York. Once at Sharps, however, Sidney discovers that he's expected to write only "safe" celebrity profiles, and that his sarcasm and brutal honesty are unacceptable. Thus, Sidney struggles to succeed at Sharps — as a writer, but also as a boorish guy in a glamorous magazine world — without relinquishing his identity altogether. Of course, there's a love story tossed in, too, so for more on that and everything else, read more.
At Sharps, Sidney meets Alison Olsen (Kirsten Dunst), a droll aspiring novelist who has no problem calling Sidney out on his impertinence. They often engage in that sarcastic banter that is actually flirtatious, but Sidney's not interested in Alison because he's too busy drooling over the beautiful young starlet Sophie Maes (Megan Fox). This storyline is so obvious and predictable, I was certain it would surprise me in the end but alas, there's not a ton of surprise at the end of this movie in general.
I really like Simon Pegg, and his uniquely awesome comedic abilities sometimes save the day here, especially in the beginning when it's funny to watch someone so socially inept act inappropriately at all times. It can be refreshing to see Sidney call out the pretentious charade of American celebrity, but we don't really root for him to succeed because he's kind of a jackass. And then, when he starts to really try to succeed, we certainly don't want him to do so by selling out and writing the crap that Clayton insists he write. But then everything you could have predicted (but didn't truly want to have happen) happens — including the incredibly generic rom-com stuff — and it's a total disappointment. Like the pitiful kid at the party, the colorful balloon of the movie deflates, and we’re left disappointed and sleepy. But then again, after a nap we'll probably forget the entire thing ever happened.
Photos courtesy of MGM