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Film / How to Lose Friends & Alienate People

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How to Lose Friends & 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, with supporting turns by Max Minghella and Margo Stilley.

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

Not to be confused with How to Win Friends and Influence People, of which the title is a parody.

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.
  • 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.
  • 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 is not impressed, and his new boss simply chucks the one Sidney gave him out a window.
  • Hard Truth Aesop: Success often comes at the expense of integrity and nonconformity.
  • 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.
  • 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.
  • 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.
  • Sexy Surfacing Shot: During a crowded party, Sophie can't seem to get around a pool to get to Eleanor and Lawrence... so she slips off her shoes and wades through the pool instead while wearing a clearly expensive low-cut dress. She emerges on the other side to a smattering of applause and stares.
  • Shout-Out: The film Sophie Maes stars in is an obvious parody of The Nun's Story.
  • Soundtrack Dissonance: In a typical Hollywood Happy Ending, the principal couple are reunited and dance to a tune from La Dolce Vita, which seems to epitomize romance for them. Problem is, that film is actually far from being romantic and optimist...
  • White-Dwarf Starlet: A sympathetic example appears at a star-studded party, ignored by the other guests and journalists in spite of her long and respectable Hollywood career. Sidney's approaching her as a fan is a big Pet the Dog moment from him, and she appears genuinely touched by the gesture.