How To Lose Friends & Alienate People chronicles Sidney Young’s descent from promising journalist to dismal failure at Sharps, New York’s most prestigious magazine. He cuts a swathe through Manhattan for all the wrong reasons and his bad manners and vulgar pranks lead to monumental mishaps with hilarious consequences, until finally and improbably he wins the heart of his true love.
In London, Sidney Young (Simon Pegg) is reporter, editor and publisher for the alternative, zero-budget Post-Modern Review magazine, a satirical rag eager to lambast the biggest egos in the entertainment world. Although he prides himself on his integrity, choosing to gush sycophantically only on his own terms, Sidney is also a looky-loo dazzled by celebrity and beauty. After a disastrous attempt to crash an awards bash, it’s something of a shock when Clayton Harding (Jeff Bridges), the New York-based editor of world-famous Sharps magazine, offers him a job!
Eager to leave the daily grind of his apartment-come-office, Sidney arrives in the Big Apple with his anarchic nose twitching. Slipping into his alter ego Clark Baxter, for whom no rule was meant to be left unbroken, Sidney plunges head first into New York’s party lifestyle and the religion of celebrity. But all is not what he hoped at Sharps. Thinking he has finally arrived, Sidney is disappointed by the straight-laced atmosphere in his new workplace and is determined to shake things up and finally get a story published. Sidney’s non-politically correct, devil-may-care attitude ruffles the feathers of his immediate superior Lawrence Maddox (Danny Huston) and instantly upsets colleague Alison Olsen (Kirsten Dunst), who so far seems to have survived the cutthroat world of glossy magazine publishing to become the magazine’s arts correspondent. Sidney’s antics (e.g., bringing a stripper to the office) and blunders (e.g., spitting food in the elevator), and getting drunk at a 4th of July party in the Hamptons, increasingly endanger his reputation and livelihood. Labelled by Maddox as Sharps’ “very own Idiot Savant, without the Savant,” Sidney is not trusted to talk to celebrities, let alone write about them.
Undeterred, Sidney has nothing but contempt for a system that prevents him from speaking his mind and has no intention of paying deference to the powers behind it, including the public relations queen of New York, Eleanor Johnson (Gillian Anderson). But his unwillingness to toe the line is soon called into question when he meets her beautiful client, actress Sophie Maes (Megan Fox). Emerging like Aphrodite from a rooftop pool, Sophie piques Sidney’s lust. But how far will he degrade himself just to be near her? Watching in bewilderment as Sidney lurches from one disaster to the next, Alison begins to see through his vulgar side and discovers an honest, thoughtful and intelligent (although often childish) man and their friendship begins to blossom. Alison’s eyes are finally opened when Sidney’s visiting father (Bill Paterson) explains that, whilst Con Air may be Sidney’s favourite movie, Sidney actually has a master’s degree in philosophy and, in his opinion, is wasting his huge talent in his ambition to become a celebrity hack. When that relationship hits the buffers, all pride is jettisoned and Sidney single-mindedly sets about making a name for himself as a ‘friend of the stars.’ He literally begs pretentious director Vincent Lepak (Max Minghella) for an interview, which is both a sycophantic and disingenuous piece, but gets Sidney the break he needs to become a successful showbiz star columnist.
Climbing the greasy pole, Sidney enters his own Shangri-la, until literally and metaphorically stripped down to his soul, his alter ego Clark Baxter resurfaces to show him the error of his ways and set Sidney on the path to winning the heart and mind of his true love.