Film: How To Lose Friends And Alienate People

How To Lose Friends and Alienate People is a 2008 comedy film loosely based on Toby Young's memoir by the same name. It stars Simon Pegg, Kirsten Dunst, Megan Fox, Jeff Bridges and Gillian Anderson.

The movie concerns a smalltime British journalist trying to make it big in New York City's world of upscale magazines. (Hilarity Ensues).


This film provides examples of:

  • Actor Allusion: One character is shown to love White Russians. His boss is played by Jeff Bridges.
  • Adam Westing: Megan Fox plays a ditzy and attractive Hollywood starlet with questionable acting skills.
  • Adaptation Name Change: Toby Young is named Sidney in the movie.
    • "Clayton Harding" is a play on Graydon Carter.
  • Alpha Bitch: Eleanor Johnson and Sophie Maes.
  • An Aesop: Success often comes at the expense of integrity and nonconformity.
  • Author Tract: Toby Young's indictment of how American journalists were sacrificing journalism for access
  • Based on a True Story: fictionalization of Toby Young's disastrous time working for Vanity Fair in The '90s.
    • Clayton Harding is its editor-in-chief Graydon Carter
    • Elizabeth Maddox is fashion editor Anna Wintour
      • The incident where Alison steps over her after she fell on the floor without once talking to her reenacts how that happened to an intern due to an unspoken rule about never talking to Anna
    • Sidney asking Bill Nathanson flat-out asking if he was gay parallels Toby asking Nathan Lane the same question in regards to his performance in The Birdcage
  • Betty and Veronica: with Alison (smart, sincere) as Betty and Sophie Maes (seductive, successful, vapid) as Veronica.
    • Sidney himself is the Betty for Lawrence Maddox's Veronica.
  • Book Ends: an early scene with the "thin red line" separating the stars from the commoners gets an Ironic Echo close to the end of the movie.
  • Brainless Beauty: Sophie.
  • Broken Pedestal: Sidney discovering that Clayton is no longer the rock-throwing Caustic Critic that Sidney idolized
  • Deadpan Snarker: many characters, but Alison probably takes the cake.
  • Fictional Counterpart: Sharp's bears quite a bit of similarity to Vanity Fair.
    • Sidney's Post-Modern Review was Toby's real-life Modern Review, which itself was a knockoff of Graydon Carter's Spy.
  • Funny T Shirt: Sidney waltzes into office on the first day of work wearing a T-shirt that reads "Young, Dumb & Full of Come". The staff of the magazine are not impressed, and his new boss simply chucks the one Sidney gave him out a window.
  • Hidden Depths: happens with at least two characters. Lawrence is the "poet" Alison was going out with. Sidney has a Master's in Philosophy.
  • Hollywood Hype Machine: discussed in-universe, with the characters of Sophie Maes and Vincent Lepak.
  • Impossibly Tacky Clothes: Sidney's wardrobe, basically.
  • Instructional Title
  • In with the In Crowd: the movie starts with Sidney, decked in a tux and an expensive watch, accompanying a foxy starlet to a gala event. The rest of the movie shows how he got to that point and whether or not it was worth it.
  • Lady in Red: Sophie during the awards ceremony.
  • Memento MacGuffin: Sidney's mother's ring.
  • Most Writers Are Writers: most of the characters are journalists, and some of them have hobbies like writing novels or poetry.
  • Ms. Fanservice: Sophie Maes, in-universe and out.
  • No Celebrities Were Harmed: Clayton Harding is based on Vanity Fair editor Graydon Carter, Elizabeth Maddox is fashion editor Anna Wintour, and Eleanor Johnson on Nadine Johnson, a high-powered publicist.
  • Not So Different: Clayton Harding, who started his journalistic career in a vein similar in Sidney's and gets a Not So Above It All moment at the end of the movie.
  • Politically Incorrect Hero: Toby/Sidney desperately trying and failing miserably to emulate the boozy brawling blackguard writers of the Algonquin Roundtable
  • Pretty in Mink: Sophie shows up to an event wearing a white fox fur wrap, despite her claims of being an animal rights activist.
  • Slobs Versus Snobs
  • Transsexual: the girl Sidney picks up at a bar on his first night in NYC.