How to Lose Friends & Alienate People is a 2008 British comedy film based upon Toby Young's 2001 memoir of the same name. The film follows a similar storyline, about his five-year struggle to make it in the United States after employment at Sharps Magazine. The names of the magazine and people Young came into contact with during the time were changed for the film adaptation. The film version (adapted by Peter Straughan) is a highly fictionalized account, and differs greatly from the work upon which it was built. It was distributed in the United States by Metro-Goldwyn-Mayer, and in the United Kingdom by Paramount Pictures and Channel Four Films (the former also distributed in Australia).

The film was directed by Robert B. Weide and stars Simon Pegg as Sidney Young, Kirsten Dunst as Alison Olsen, Jeff Bridges as Clayton Harding, Danny Huston as Lawrence Maddox, Gillian Anderson as Eleanor Johnson, and Megan Fox as Sophie Maes. The cast also includes Max Minghella and Margo Stilley. How to Lose Friends & Alienate People was released in both the United States and United Kingdom on 3 October 2008.


How to Lose Friends & Alienate People (film)

Sidney Young (Simon Pegg) is a smalltime, aspiring English journalist who works for a left-wing radical magazine. Following an incident at a party where Sidney accidentally lets a pig loose, he is hired to work for an upscale magazine in New York City. He is hired by Clayton Harding (Jeff Bridges), editor of Sharps magazine, a man Sidney had previously lampooned in his own magazine.

Sidney annoys the staff he works with, first Alison Olsen (Kirsten Dunst), who is only there to pay the bills whilst she finishes her book, then his boss Lawrence Maddox (Danny Huston). He also dares to target the star clients of power publicist Eleanor Johnson (Gillian Anderson). He then meets new rising star Sophie Maes (Megan Fox); however, he is told by Lawrence not to talk to her. Sidney makes it his mission to become something within the business; however, it is almost ruined when he accidentally kills Sophie's dog Cuba, as he was able to stop the dog from going out the window but unfortunately could not stop a vase from falling onto the dog. Luckily, Alison covers for him and nobody else finds out it was him.

At a party, Alison and Sidney's relationship grows when she reveals she has just ended an affair with Lawrence. Sidney stops her from driving home drunk, causing him to miss his opportunity to sleep with Sophie. At a later party, however, just when Sidney was about to ask her out, it is revealed Lawrence has left his wife and that he and Alison are officially together. In a desperate attempt to up his career, he begs Eleanor to publish a piece on Vincent (Max Minghella), a director he truly hates.

The next day at work Clayton reveals that both Alison and Lawrence have left, and he promotes Sidney. Sidney finally becomes successful, getting all the girls that were disgusted by him before and even catching the eye of Sophie. The night before the awards ceremony she stated that if he gave her his late mother's ring and she won best actress, she would have sex with him. Going to the ceremony the next day he sees Lawrence, now being someone he used to be, stating that he and Alison split as she was in love with him. When the winner is revealed (Sophie), as she is going to get her award, he realizes he does not really love her and asks for his ring back, then, after a heated exchange, he steals back the ring from Sophie, and inadvertently (because of anger) reveals that he killed Cuba. An enraged Sophie attacks him and a huge fight ensues. After the fight, Sidney leaves, quitting his job at Sharps and heading to New York.

He meets Alison in the park, where they were showing her favourite movie, La Dolce Vita. She has finished her book and the two finally get together, with him giving her his mother's ring. The movie ends with him accidentally throwing the book onto a candle and jumping for it to stop it from going into flames.


  • Simon Pegg as Sidney Young, a British journalist. He is based on Toby Young as he is portrayed in the memoir.
  • Kirsten Dunst as Alison Olsen, Young's colleague and eventual love interest.
  • Megan Fox as Sophie Maes, a budding starlet and the object of Young's lust.
  • Danny Huston as Lawrence Maddox, Young's direct boss.
  • Gillian Anderson as Eleanor Johnson, the publicist pulling all the strings. Eleanor is loosely based on Nadine Johnson, a high powered publicist in New York City.
  • Jeff Bridges as Clayton Harding, Young's magazine editor who is loosely based on Graydon Carter, the editor of Vanity Fair.
  • Bill Paterson as Lord Richard Young, Sidney's father; loosely based on Toby Young's father, Michael Young, Baron Young of Dartington
  • Max Minghella as Vincent Lepak, a young up-and-coming director whom Sidney despises
  • Miriam Margolyes as Mrs Kowalski, Young's landlady
  • Margo Stilley as Ingrid, Young's work colleague
  • Jefferson Mays as Bill Nathanson
  • Nathalie Cox as Woman in Bar
  • Charlotte Devaney as Bobbie

Minor appearances and cameos

  • Brian Austin Green in a cameo
  • Thandie Newton as herself
  • Chris O'Dowd as Co-Worker
  • James Corden as Co-Worker
  • Katherine Parkinson as PR woman

Due to the subject matter of the film, a number of well known faces appear in archive footage, including Ricky Gervais, Kate Winslet, and Daniel Craig.


How to Lose Friends & Alienate People is an independent film, and was described as "a testosterone-laced [The] Devil Wears Prada."

In 2006, Simon Pegg was announced as the lead, Kirsten Dunst was revealed to appear in the film in late April 2007, and in May 2007, Jeff Bridges and Gillian Anderson were added. Toby Young, who wrote the memoir, was banned from the set because he was constantly annoying the cast and crew. He does appear in the film though, with a brief cameo in the background of a party scene.

Metro Station's song "Shake It" and Phantom Planet's song "Do The Panic" were used in the trailer.

Box office

How to Lose Friends & Alienate People (film)

The film opened as one of the UK's box office number one films, taking the equivalent of US$7,055,425 during its run there. It took the equivalent of US$2,927,210 in Russia and the equivalent of US$1,963,356 in Australia. In the United States and Canada, the film grossed the equivalent of just US$2,778,242.

The total worldwide gross was about US$19 million, 40% less than the production budget.


The film has received mostly negative reviews. It currently holds a 36% "rotten" rating on Rotten Tomatoes, with the critical consensus, "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." The Spectator called the film "fun," but noted that it "yaps around the ankles of its subject without ever moving in for a decent-sized, satisfying bite." On the other hand, The Sunday Times said the film "has more laughs than any British comedy to appear over the past decade."

In the U.S., Roger Ebert called it "possibly the best movie that could be made about Toby Young that isn't rated NC-17" and gave it 3½ out of 4 stars.


External links

  • Official website
  • How to Lose Friends & Alienate People at the Internet Movie Database
  • How to Lose Friends & Alienate People at AllMovie
  • How to Lose Friends & Alienate People at Rotten Tomatoes
  • How to Lose Friends & Alienate People at Box Office Mojo
  • Toby Young and Stephen Woolley video interview with ITV

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