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.
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