Simon Pegg has made a career playing likable losers. Whether it was his slacker hero in horror-comedy Shaun of the Dead or his Super Cop with no personality in Hot Fuzz, he always proves to be extremely likable despite all his characters’ personality flaws. In How to Lose Friends & Alienate People, he faced his greatest challenge. He had to turn a complete jerk into someone we could stand behind and cheer for.

In this challenge Simon Pegg succeeded. Unfortunately, the rest of the movie failed to match up with the charisma of its lead. While his work with Edgar Wright has produced some true modern classics, this movie is utterly forgettable and is another bump in the road of Pegg’s American career.

Based on the novel by Toby Young, How to Lose Friends & Alienate People tells the story of one man’s inability to do the right thing as he continuously screws up in his job at Vanity Fair magazine. Renamed Sidney Young, Pegg’s character begins the movie working for a magazine that appears to operate out of an apartment. He gets a call one day from magazine mogul Clayton Harding (Jeff Bridges) and is offered a job at Sharps Magazine, one of the most prestigious celebrity magazines on the market.

When he shows up for his first day of work, he is wearing a t-shirt with the quote “Young, Dumb and Full of Cum.” It is these types of paint-by-numbers shots that annoy me in this movie. Yes, Young is an idiot, a loser who doesn’t know when he needs to act normal. I want them to show me in what he does, such as when he is trying to hit on women by saying all the wrong things. The movie feels like it was made as a how-to-be-a-loser for dummies and is overly simplistic in its development.

The plot is also simple. Young wants to be a great writer. He chooses to go about this dream by flaming and insulting anyone who is famous. He has some morals and when he faces an actress he respects, he gives her the utmost courteousy, but when he meets people who are the “flavor of the day” he would rather throw insults. He says in the film, he is only great when he pisses people off. The only person he does not do this to is Sophie Maes (Megan Fox), an actress he wants to sleep with.

The movie is a typical romantic comedy as Young is a man who wants to sleep with one woman (Sophie) but can’t see that another woman, Alison Olsen (Kirsten Dunst), might be interested in him. There is also a love triangle concerning one of his editors (Danny Huston) with both women.

Pegg is outstanding in his role. If anyone else had been cast, I don’t think I could have made it through the movie. So many scenes were plotted in an elementary manner, to the point of being unoriginal. If you have ever seen a movie, you will know what is going to happen five minutes before it does.

I also have complaints about a number of things thrown into the movie but never expanded on. There is a gag about never looking the boss’ wife in the eyes that is never explained. It gave one weird moment that was slightly amusing, but it made no sense and appeared added for no reason other than adding a couple of minutes running time. When Young finally makes his big decision at the end of the movie, it ends and you don’t know what happens next.

If you want to see this movie as a romantic comedy, it might deliver in a very shallow way. If this is your desire, the ending would slightly satisfy you. I went into the movie expecting a man and his eventual discovery of life’s important lessons. On that basis, the movie fails and is disappointing.

Young gets the job at Sharps and sticks to his morals in the beginning. Eventually, he reaches his breaking point and sells out, becoming the man he was raving against at the start of the movie. Finally, he realizes what he has become and self destructs in a manner making you cheer for him as he destroys everything he has built. It sounds good on paper but never comes across as inspiring or engrossing.

The Verdict

How to Lose Friends & Alienate People stars one of the hottest comic talents in the world today. Unfortunately, the humor feels forced and never truly delivers. Simon Pegg does the best he can with what he is given and makes you care about his character. Unfortunately, the movie doesn’t know if it wants to be a romantic comedy or an inspirational story. At the end of the day, it is a disappointing film that could have been much better.