Reviewing How to Lose Friends and Alienate People


We extend our warmest welcome to you, our dear readers. We are very pleased to present you with our newest project – a webpage dedicated to the fantastic 2008 comedy titled How to Lose Friends and Alienate People.

We are a bit disappointed that the film never hit the popularity level it deserved at the time it was released, so we decided to make this page to prove to people that this comedy is in fact a sleeper.

We hope our review of the film influences more people to watch it, now that older films and shows experience renewed interest due to the pandemic and our obsession with streaming services.

We also hope to change the negative opinion of people who have seen it but don’t quite like it. We feel like a lot of people either didn’t like the experimentation with the genre of romantic comedy or thought that the execution didn’t hit the mark. We will discuss these negative attitudes and what might have caused them.

On this page, you can find why the film was made in the first place, such as its creative influences that surprisingly came from spending time on legal online gambling sites. We will also briefly touch upon background information about the people involved in the project. We will tell you more about the cast and how it performed in the box office. Last, but not least, we will discuss the themes the film explores and how they were developed in the plot.

Now, sit back and relax with our light-hearted review of How to Lose Friends and Alienate People. I hope you enjoy reading it!

Inspiration for the Film

Overview of How to Win Friends and Influence People by Dale Carnegie

Unlike most of the romantic comedies you can find today, How to Lose Friends and Alienate People is in fact a true story. Yes, we know how insane that sounds, but did you really think that the world of celebrity publishing was sane? The book, bearing the same name as the film, is the work of Toby Young. Toby Young is the child of Lord Young of Dartington, a Labour life peer, who is famous for coining the term “meritocracy” and for espousing these values, similar to his son nowadays. Toby Young is a supporter of the British Conservative Party and a co-founder of the Free Speech Union.

Now let’s go back to the book. Young published his memoir How to Lose Friends and Alienate People in 2001. The title is a copy of the title of the Irving Tressler parody (1937) of the Dale Carnegie book How to Win Friends and Influence People (1937), although Young doesn’t reference either author in his memoir.

Young’s memoir details his life as a contributing editor to Vanity Fair. Similar to other famous and talented Brits like Anna Wintour and Alfred Hitchcock, Young wanted to make it big in the USA, so he moved there in 1995 to work for the famed magazine.

The style of his memoir is satirical as it depicts Young’s struggle to mangle with American journalists and notable celebrities like Mel Gibson. It also portrays some of his low points in a hilarious fashion such as his eventual firing from Vanity Fair in 1997 and even his dismissal from a New York Alcoholics Anonymous group.

We highly recommend this fascinating book to those of you who haven’t read it. Now it’s time to take a look at how it was adapted for the big screen.

Adapting a Memoir

It’s never an easy task to adapt a book into the conventional 90 or 120 minutes of screen time. Things would always be left out due the nature of adaptation, but the important question every filmmaker should ask themselves is how to recreate the spirit, the soul of a book in a cinematic form.

Some reviewers believe that the film failed that task. The short critic consensus you can read on Rotten Tomatoes states “[a] decent performance from Pegg in a disappointing film. Neither sharp nor satirical, Weide’s adaptation relies too heavily on slapstick, and misses the point of the source material in the process.”

We believe these words a tad too harsh, but there’s some truth in them. Although we love the slapstick moments in the film such as the pig Britney ruining the BAFTA’s after party, perhaps the director should have used them more sparingly than he did. Perhaps his work on Curb Your Enthusiasm influenced his artistic decisions.

We do not, however, agree that the point of the memoir was completely lost.

It’s true that Sidney Young is more unlikable than his real-world counterpart, Toby Young, but we get the same fresh foreign perspective of a Brit navigating corporate America. Neither Sidney nor Toby are John Oliver’s; they are the Brittiest Brits with the stingiest humor you can find and they don’t care what Americans have to say about it.

What is perhaps the biggest stray away from the book is the director’s decision to turn the movie into a romantic comedy. Toby Young did find love, his future wife Caroline Bondy, in New York, but the memoir wasn’t really a story about his quest for love, although it did include events from his dating experience in the US.

Some might view this as a betrayal of the source material, but we personally believe it was a nice expression of artistic liberty. Can we all agree that we are tired of Hallmark-y mass-produced romantic comedies? Well, director Robert B. Weide certainly thought so and gave us this fresh perspective on the otherwise stale genre.

Overall, the movie doesn’t claim to be an outright dramatization of the novel. It’s loosely based on it. The name of the protagonist was changed, along with the names of other real people.

Vanity Fair became Sharps and Young’s own magazine became Postmodern Review; it was called Modern Review in real life, but the director made a clever joke by turning it into “postmodern” as the nature of film based on the adaptation of a memoir is essentially a postmodern work.

There are of course added characters such as those of Alison Olsen and Sophie Maes. Due to their inclusion, the plot also diverted from the events of the memoir, which allowed it to become a romantic comedy in the first place.

We feel it’s time to talk more about the film such as the members of the cast, the production schedule, and of course, the film’s plot as well.

Main Cast


  • Simon Pegg as Sidney Young
  • Kirsten Dunst as Alison Olsen
  • Megan Fox as Sophie Maes
  • Danny Huston as Lawrence Maddox
  • Gillian Anderson as Eleanor Johnson
  • Jeff Bridges as Clayton Harding
  • Bill Paterson as Lord Richard Young
  • Max Minghella as Vincent Lepak
  • Miriam Margolyes as Mrs. Kowalski
  • Margo Stilley as Ingrid

Main Crew

  • Robert B. Waide – Director
  • Peter Straughan – Screenwriter
  • Stephen Woolley – Producer
  • Elizabeth Karlsen – Producer
  • Oliver Stapleton – Cinematographer
  • David Freeman – Editor
  • David Arnold – Music Composer


How to Lose Friends and Alienate People was first teased in 2006 with the news that actor Simon Pegg would fill in the shoes of the opinionated Toby Young. The following year, other members of the cast were revealed and production officially began in 2007.

Of course, the man himself, Young, was on set to give cues to the cast and crew. One particular cue, however, was interpreted as an insult by the rising star Kirsten Dunst. After this incident, director Robert Waide limited Young’s visits to the set. Still, Young makes a small cameo in one of the party scenes.

How to Lose Friends and Alienate People was made by two independent film studios based in the United Kingdom – Number 9 Films and Film4 Productions. It was distributed by Paramount Pictures in the UK and by Metro-Goldwyn-Mayer in the US.

The budget for the film was $28 million and it officially premiered on 3rd October 2008. Unfortunately, it failed to even break even since it only made $19 million worldwide.

Until now, this overview was spoiler-free, but this is about to change in a moment. If you want to watch the film, we advise you to stop reading now and come back later after you’d seen it to avoid it being spoilt for you.

Here’s the trailer, so you can get an idea of what the film is like.

Film Review

Now that we have all these details, let’s talk about the film itself. How to Lose Friends and Alienate People has the classic freeze-frame structure of comedies at the time. It opens up with Sidney watching a black-and-white British film that we later discover features his deceased mother.

He narrates how he believed that all stars live in a magical place, Shangri-la, and how he would be “happy forever” once he gets inside. A flashforward occurs and we see Sidney attending the Apollo Film Awards with Sophie aka being inside this Shangri-la.

Sidney then turns to the camera and breaks the fourth wall by directly referring to the audience and revealing his life was much different before. The doors of the auditorium open up as if opening up the source of Sidney’s memories and we see him trying and failing to get access to the BAFTA awards a year prior.

We learn that Sidney operates a magazine, Postmodern Review, which is close to bankruptcy. Apparently, a lot had changed for a year to get from an unknown guy trying to make his break to the Armani-clad date of an upcoming actress.


We see his first stint of trying to pass a pig as the star of the hit film Babe and almost being successful. We start rooting for this underdog who knows his way around celebrities, at least how to make them laugh. Thandie Newton makes an appearance as herself and Sidney had just broken the ice with her when pig Britney arrives and causes mayhem, roll credits.

We then see Sidney’s apartment/magazine headquarters over a kebab shop in London. He’s proudly cutting out a picture of Clint Eastwood having him in a chokehold, meaning that such occurrences are frequent.

The mismatched (and unpaid) staff of Postmodern Review brilliantly represents the core values of the magazine – “low culture for high brows” (a quote from Toby Young) as two people argue, and later fight, about philosophers, while others simply cannot bring themselves to care.

Sidney receives a call from Clayton Harding and gives a passionate David versus Goliath speech of how he has principles and can’t be bought, but leaves immediately when he’s offered a position at Sharps.

This is the first scene showing the main conflict of the film and that of the protagonist; Sidney acts like he’s above things and that he’s somehow different than the shallow journalists, but he’s just as starstruck and fame obsessed, if not even more.

He’s also kind of an a-hole. He wastes no time to show us in his fiery exchange with Alison. Still, we can’t say we dislike it. In our opinion, there aren’t enough antihero protagonists in comedies and the way in which his British humor often doesn’t land in the US is hilarious.

Sidney is the epitome of fish-out-of-water in this glitzy US magazine, as many reviews note. We get a small glimpse of hope for our hero when he meets his boss, Clayton Harding, as we find out Harding had a satirical magazine, Snipe, in his youth, which inspired Sidney to create Postmodern Review.

Our hopes are soon crushed as the exchanges between Sidney and Harding and then Sidney and Maddox are simply awkward. We then discover that the woman Sidney tortured at the bar, Alison, is his colleague. Sidney is assigned to work at the “I Spy” department, which reports on celebrity sightings; a window to high society, or the perfect place for starstruck Sidney. He immediately acts unprofessionally by calling a famous artist fat and finding nothing wrong with that.

Sidney tries to distinguish himself from the “glossy posse” masses at Sharps, but the question is whether he’s truly different or simply arrogant and offensive. Alternatively, maybe he’s just English, as Alison notes.

Apparently, in England journalists are treated badly and they respond with the same, at least according to Sidney, but he soon finds out that celebrity correspondents in the US are some sort of demi-gods who decide what’s “hot”. Maddox thinks the hot thins is director, Vincent Lepak, a vapid and shallow type.

He ignores an older actress, Rachel Petkoff, despite Sidney’s pleas to write a profile on her comeback, although Maddox later proposes the same and passes the idea as his.

The parallel between Rachel and Vincent means to show the disconnect of the American celebrity culture, but it’s hard to say if Sidney stands for “true art”, especially when he unironically says that Con Air is the best film ever made.

The film struggles to take a side in this debate, which could be a mistake on its part, or maybe it doesn’t want to take a side and let Sidney be the chaotic neutral character of the story. Is he a genius or an idiot? Is he inspired or utterly done with everything? We might never find out.

Returning to the action, we see the first instance of romance in the romantic comedy when Sophie Maes appears and she’s as dreamy as you can imagine. Sidney reacts more like a cartoon character, a Bugs Bunny with hearts popping out of his eyes, rather than a real person.

Naturally, his jokes don’t land with her and she leaves the party with Maddox who becomes an antagonist in both Sidney’s personal and professional life. Sidney now wants to tone down his attitude only to get to Sophie before Maddox does, but his worldview stop him from doing this as shown in his refusal to write a flattering profile of Vincent.

It didn’t help either that he accidentally caused the death of Cuba, Sophie’s dog. Killing dogs is a bold move in the film business, but we were pleasantly surprised by the good execution; pun unintended.

Sidney is finally given a chance to express his unaltered opinions by Clayton who allows him to show Vincent for who he is in a rare moment of clarity. He quickly backtracks, however, returning to his corporate stance on snarky pieces.

Despite the threat of contract termination, Sidney finally gets something going for him when he sees drunk Sophie. You get this classic Hollywood moment of them two coming together as Sophie reveals she’s not as vapid as everyone thinks, but just when you think they’d get together, Sidney leaves her to help Alison.

This makes us realize that we were bamboozled to think the romantic story was about Sidney and Sophie, when it was always going to be Sidney and Alison. Richard, Sidney’s dad, makes the discovery for us and reminds his son of his potential, in a sort of Simba-Mufasa exchange.

Although we liked both Pegg’s and Dunst’s performances, we can’t say we feel any chemistry. They work great as a comedic duo, but their romance felt rather forced. Everyone loves a plot twist as long as it makes sense.

Maybe some negative reviews have a point; you cannot tell the viewers “these two people like each other, accept it” and set a completely different tone in the following scene. The movie might have worked better if that wasn’t the angle. Alternatively, they could have excluded that Richard Young scene to let the viewer see for themselves.

Although Alison went back to Maddox, Sidney finally has something going for him after Maddox was fired. He becomes the deputy editor and we get the traditional comedic montage of the changes in his life – how he’s sucking up to celebrities, and how they suck up to him, how he’s invited to every event etc.

He even gets a second chance with Sophie as we see her warming up to him. However, we find out that she uses him as a lackey, much like Alison predicted. Sidney realizes he never actually wanted to be in Shangri-la and that this mystical place doesn’t exist at all.

The film comes full circle with the Apollo Awards ceremony. First, it goes back to the beginning before the flashback, and second, it’s thematically tied to the first scene from the flashback, the BAFTA’s party.

This time, however, Sidney is not trying to get in, but get out. After receiving a wake-up call by seeing his mother on screen and then finding out Alison is in love with him, he purposefully ruins the ceremony and starts an actual fight with Sophie.

This is one of the strongest scenes in the movie that captures the personality of each character and the morale of the story. We also really liked Jeff Bridges’ chuckle followed by a poker face.

Just like other romantic comedies before it, How to Lose Friends and Alienate People had to end with the hero chasing after the girl. He finds her at a La Dolce Vita’s screening and they finally get their kiss and their dance.

Final Comments

Overall, we really like this comedy and believe it’s highly underrated, especially in terms of the performances and the humor itself. We do understand the critiques, but we feel like the positives outweigh the negatives and that we’d rather watch this than most other romantic comedies from the same period.