How to Lose Friends & Alienate People (film)

How to Lose Friends & Alienate People

Theatrical release poster
Directed by Robert B. Weide
Produced by Stephen Woolley
Elizabeth Karlsen
Screenplay by Peter Straughan
Based on How to Lose Friends & Alienate People
by Toby Young
Starring Simon Pegg
Kirsten Dunst
Danny Huston
Gillian Anderson
Megan Fox
Max Minghella
Jeff Bridges
Margo Stilley
Music by David Arnold
Cinematography Oliver Stapleton
Edited by David Freeman
Distributed by Paramount Pictures
(United Kingdom)
(United States)
Intandem Films
Release dates
  • 3 October 2008 (2008-10-03) (United Kingdom)
Running time
111 minutes
Country United Kingdom
Language English
Budget $28 million[1]
Box office $19,151,797[2]

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.[3] 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.


Sidney Young (Simon Pegg) is a petty 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 affluent magazine in New York City. He is hired by Clayton Harding (Jeff Bridges), editor of Sharps magazine, a man Sidney had previously satirised in his own magazine.

Sidney frustrates 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 a somebody within the business; however, it is almost ruined when he accidentally kills Sophie's dog Cuba; trying to play with the dog, Sidney threw a ball that accidentally went out his office window and as he stopped the dog from going out the window he unfortunately proceeded to cause a vase to fall onto the dog. Luckily, Alison covers for him and nobody else finds out it was him.

At a party, Alison and Sidney's relationship strengthens 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 an eager attempt to boost his career, he begs Eleanor to publish a piece on Vincent (Max Minghella), a director he intensely dislikes.

The next day at work Clayton reveals that both Alison and Lawrence have left, and he promotes Sidney. Sidney finally becomes successful, attracting all the girls that were previously repulsed by him 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 up as she was in love with Sidney. When Sophie is announced as the winner, as she is going to collect her award, he realizes he does not truly love her and asks for his ring back, then, after a heated argument, he steals back the ring from Sophie, and inadvertently (because of anger) reveals that he killed Cuba. A furious Sophie assaults him and a huge fight ensues. After the fight, Sidney leaves, quitting his job at Sharps and heads back to New York City.

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 burning into flames.


Minor appearances and cameos

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."[1]

In 2006, Simon Pegg was announced as the lead,[4] Kirsten Dunst was revealed to appear in the film in late April 2007,[5] and in May 2007, Jeff Bridges and Gillian Anderson were added.[6] Toby Young, who wrote the memoir, was banned from the set because he was constantly annoying the cast and crew. [7] 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

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.[8] 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.[2]

Critical reception

The film has received mostly negative reviews. It currently holds a 36% "rotten" rating on Rotten Tomatoes,[9] 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."[10] On the other hand, The Sunday Times said the film "has more laughs than any British comedy to appear over the past decade."[11]

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.[12]


  1. 1 2 3 McGee, Celia (2007-10-14). "Sweet Smell of Revenge (Screen Version)". Retrieved 2007-11-16.
  2. 1 2 How to Lose Friends & Alienate People at Box Office Mojo
  3. Landesman, Cosmo (5 October 2008). "How to Lose Friends & Alienate People". London: The Times. Retrieved 5 October 2008.
  4. "Simon Pegg Is Toby Young". 2006-09-18. Retrieved 2007-11-16.
  5. "Blonde On Blonde, Dunst joins Pegg for journo comedy...". 2007-04-23. Retrieved 2007-11-16.
  6. "Pegg Makes Friends, Big names join journo flick...". 2007-05-13. Retrieved 2007-11-16.
  7. Young, Toby (September 2008). "Why Kirsten Dunst banned me from the set of the film about my life". The Spectator. Retrieved 2016-09-09.
  8. International Box Office from Box Office Mojo
  9. "How to Lose Friends & Alienate People". Rotten Tomatoes. Retrieved 2014-01-14.
  10. Losing is the new winning 1 October 2008, The Spectator
  11. How to Lose Friends & Alienate People makes a big star of Simon Pegg, 5 October 2008, The Sunday Times
  12. Review of How to Lose Friends & Alienate People by Roger Ebert

External links

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