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A British writer struggles to fit in at a high-profile magazine in New York. Based on Toby Young's memoir How to Lose Friends & Alienate People.
Sidney Young (Simon Pegg) is an arrogant, impudent, sarcastic, rude, and loathsome journalist itching to stir things up. He is hired for that reason by Clayton Harding (Jeff Bridges), the boss of a popular entertainment magazine.
This is a lead character that is really our anti-hero because he has qualities that aren't the greatest in most people's morality sense. A common trend in TV and movies in the last few years where we follow the journey of a person who we probably don't want to be or really look up to. Or maybe we do look up to them?
What do Tony Soprano (The Sopranos), Tony Stark (Ironman), Don Draper (MadMen) and Sidney Young all have in common? Their selfish people who really only care about themselves. Why do we like them and follow them on their journeys? Because they all have the great quality most of us look for: Confidence!
All of these men always face their fears and any conflict that arises head on, while also going above and beyond to push themselves into interesting life situations. They all have no fear. Yes, of course they do fear like we all fear, but these characters try their hardest to squash their conscious fears as soon as they can.
And consciously, or unconsciously, that's why we like them because most of us (me included many times) don't do what they do. Confidence goes a long way. Even if you murder people like Tony Soprano, or manipulate people for their own benefit like Sidney Young does in How to Lose Friends & Alienate People, we follow them because of this major quality they possess.
And confidence is what Sidney possesses. He's not afraid of celebrities really or anyone for that matter. He's not afraid to speak his mind in any situation because that's what he feels. Sidney thinks that what he thinks, does what he wants to do and says what he wants to say because he feels he is the most important person in the world. Some would call it blind and ignorant confidences, but confidence is confidence and most of us want it.
There's a lot I liked about How to Lose Friends and Alienate People. The most important relationship is between Sidney and his boss Clayton. In one scene Sidney asks Clayton straight out why did he hire him because he obviously doesn't fit in.
Clayton is a cliche in many ways. But an important cliche. He's a former maverick/hippie who started his own magazine way back then to take down the 'man' in order to get the truth out there. His intelligence and determination made him rich and famous because he did take down the man a bit and stir things up. But what happens when you succeed in America is that you become part of the 'man'. Clayton was aware of that and he thought he would always stay true to his integrity while doing the job of spoon feeding his 'people' and always make sure the truth goes out there.
A lot happens in 20 years and Clayton has found himself in a position of advertisers and publicists really running things. In order for something to be popular, you must shake hands with the
Enter Sidney to stir things up and perhaps help Clayton find his past again in order for him to also find his integrity. That's a great story but it's only one of the sub-plots. The other sub-plot where Sidney falls for an A-list actress while also having feelings for his co-worker (Kirsten Dunst) was tired and in 'I've seen this before' mode.
All in all though there is a lot of charm in How to Lose Friends and Alienate People. Simon Pegg, the British actor who plays Sidney, is a very talented actor who you can help but feel for when he's on screen no matter how selfish he can be. An almost perfect casting choice.
How to Lose Friends and Alienate People also takes a shot at the celebrity obsessed world we also live in too. It seems that everyone really is working for the publicists of the celebrities. The cameramen, the magazines, the news shows on TV, all the way down to us, the audience. If an actress walks down the street and buys an orange at the convenience store, it's news for some reason. That's the world we live in because the powers that are make a lot of money from it. And they make a lot of money because we care.
And the question is why do we care? Probably because we are a species who loves Soap Operas and drama. Be it daytime or primetime TV shows or WWE Wrestling, we love storylines that occur in situations that most of us don't know about. It's our own inside version of Science Fiction. And How to Lose Friends and Alienate People tells us how the system works and how a guy like Sydney Young can also be famous for following the famous.
I wonder where we'll be in 100 years.