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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 Creator/SimonPegg, Creator/KirstenDunst, Creator/MeganFox, Creator/JeffBridges, and Creator/GillianAnderson, with supporting turns by Creator/MaxMinghella and Creator/MargoStilley.

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

Not to be confused with ''Literature/HowToWinFriendsAndInfluencePeople'', of which the title is a parody.

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!!This film provides examples of:

* ActorAllusion: One character is shown to love White Russians. [[Film/TheBigLebowski His boss is played by Jeff Bridges.]]
* AdamWesting: Creator/MeganFox plays a ditzy and attractive Hollywood starlet with questionable acting skills.
* AdaptationNameChange: Toby Young is named Sidney in the movie.
** "Clayton Harding" is a play on Graydon Carter.
* AlphaBitch: Eleanor Johnson and Sophie Maes.
* AuthorTract: Toby Young's indictment of how American journalists were sacrificing journalism for access
* BasedOnATrueStory: Fictionalization of Toby Young's disastrous time working for ''[[Magazine/VanityFair Vanity Fair]]'' in TheNineties.
** 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 ''Film/TheBirdcage''
* BettyAndVeronica: with Alison (smart, sincere) as Betty and Sophie Maes (seductive, successful, vapid) as Veronica.
** Sidney himself is the Betty for Lawrence Maddox's Veronica.
%%** BeYourself
* BookEnds: an early scene with the "thin red line" separating the stars from the commoners gets an IronicEcho close to the end of the movie.
%%* BrainlessBeauty: Sophie.
* BrokenPedestal: Sidney discovering that Clayton is no longer the rock-throwing CausticCritic that Sidney idolized
* DeadpanSnarker: Many characters, but Alison probably takes the cake.
* FictionalCounterpart:
** ''Sharp's'' bears quite a bit of similarity to ''Magazine/VanityFair''.
** Sidney's ''Post-Modern Review'' was Toby's real-life ''Modern Review,'' which itself was a knockoff of Graydon Carter's ''Spy.''
* FunnyTShirt: 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.
* HardTruthAesop: Success often comes at the expense of integrity and nonconformity.
* HiddenDepths: happens with at least two characters. [[spoiler:Lawrence is the "poet" Alison was going out with. Sidney has a Master's in Philosophy]].
* HollywoodHypeMachine: discussed in-universe, with the characters of Sophie Maes and Vincent Lepak.
* ImpossiblyTackyClothes: Sidney's wardrobe, basically.
* InstructionalTitle
* InWithTheInCrowd: 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.
* MementoMacGuffin: Sidney's mother's ring.
* MostWritersAreWriters: most of the characters are journalists, and some of them have hobbies like writing novels or poetry.
* MsFanservice: Sophie Maes, InUniverse [[Creator/MeganFox and out]].
* NoCelebritiesWereHarmed: Clayton Harding is based on ''Magazine/VanityFair'' editor Graydon Carter, Elizabeth Maddox is fashion editor Anna Wintour, and Eleanor Johnson on Nadine Johnson, a high-powered publicist.
* PoliticallyIncorrectHero: Toby/Sidney desperately trying [[HilarityEnsues and failing miserably]] to emulate the boozy brawling blackguard writers of the Algonquin Roundtable
* PrettyInMink: Sophie shows up to an event wearing a white fox fur wrap, despite her claims of being an animal rights activist.
* SexySurfacingShot: 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 [[EatingTheEyeCandy stares]].
* ShoutOut: The film Sophie Maes stars in is an obvious parody of ''Film/TheNunsStory''.
%%* SlobsVersusSnobs
* SoundtrackDissonance: In a typical Hollywood HappyEnding, the principal couple are reunited and dance to a tune from ''Film/LaDolceVita'', which seems to epitomize romance for them. Problem is, that film is actually far from being romantic and optimist...
* WhiteDwarfStarlet: 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 PetTheDog moment from him, and she appears genuinely touched by the gesture.
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