How to Lose Friends Alienate People 2008 Movie Scene Simon Pegg as Sidney Young in an elevator with three tall and beautiful models

How to Lose Friends & Alienate People [2008]

Behind this long-ass title How to Lose Friends & Alienate People hides a mildly entertaining romantic comedy starring Simon Pegg. It’s based on Toby Young’s memoir of the same name. However, you should know that Toby exaggerated and made up a lot of this stuff. At least he’s an interesting character to dissect. For example, he was banned from the set as he kept pestering the actors. It turns out that the guy is a real menace, unlike the charming Sidney Young we see in the movie. And that was all down to Simon Pegg’s stunning performance. The man is a fucking genius.

I also want you to know that this movie is not as edgy or funny as some of his previous ones. You can feel that his missing his buddies Edgar Wright and Nick Frost. The three of them were the driving forces behind such masterpieces as Shaun of the Dead and Hot Fuzz. Moving on, the story in How to Lose Friends & Alienate People revolves around celebrities and trashy magazines. We follow young Toby as he moves to New York in pursuit of his dreams. He’s that kind of annoying coworker who will just keep drilling and drilling until he finds something.

You might say that he’s perfectly suited to work in the US with this type of attitude. This is a forgettable and lighthearted comedy that’s going to keep your attention for ninety minutes. There will be some outrageous scenes, a bit of snappy dialogue and before you know it, you’ll have to face that existential dread again. I also want you to pay attention to editing as it showcases how you can effectively hide many flaws your movie has. If you compare it to a much bigger movie featuring a similar setting, The Devil Wears Prada, you’ll see all of these flaws on display.

Meet Sidney Young, a daring celeb journalist who’s not afraid to try and do anything to get the next big scoop. After he pulls another one of his crazy stunts, involving a pig, he ends up in New York, working for the big Sharps magazine. Excited and ready to take America head-on, Sidney is going to continue to bumble his way forward.

I think that this would be a much better and funnier movie if they went all-out with the jokes. Where are my shitting and crazy sex scenes? I was expecting, as I’m guessing most of the viewers were, a raunchy comedy, and what I got instead is a mainstream production catering to the Average Joe. Still, the quality of the jokes and performances is sufficient enough to warrant a viewing. And to be fair, there will be some pretty zany scenes like the one with the nude shemale.

Plus, you can look at the movie as a character study. After all, its title is How to Lose Friends & Alienate People. Although I think that all you can think about right now is how a nude shemale fit into all of this…

Director: Robert B. Weide

Writers: Peter Straughan, Toby Young

Cast: Simon Pegg, Megan Fox, Gillian Anderson, Kirsten Dunst, Jeff Bridges

Fun Facts: Megan Fox signed on to star in this movie before she agreed to appear in the first Transformers movie. Robert B. Weide, the director of How to Lose Friends & Alienate People was certain that he discovered the next big star and hoped he will get the credit for it. However, after the huge success of the Transformers movie, his dreams were dashed.


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