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How to Lose... is Young's own telling of his disastrous five-year career in New York journalism, initiated when he is offered a job at Vanity Fair, Conde Nast's flagship star-fest. Young may have been hired for his snappy prose, but his real genius turns out to be antagonising the rich and famous. He is the British bulldog in the Armani-clad china shop of the politically correct glossy posse. He hires a strip-o-gram on bring-your-daughter-to-work day, commits the cardinal sin of asking celebs about their religion and sexual orientation, gets blasted on coke while trying to do a photo shoot and spends less time pulling up his chair to the modern day equivalent of the Algonquin table than trying to blag his way past "clipboard Nazis" barring his way into showbiz parties. Oh, and he gets sued by Tina Brown and Harold Evans. This is the place, he soon discovers, where greatness is measured not in your prose stylings, but how far up the guest list you are for Vanity Fair's Oscar party. But two things raise this particular loser's story above the crowd. First is his spot-on outsider's inside observations on phenomena such as the rigidly Austen-ite New York dating scene. Second, he has the columnist's knack of connecting everyday experience to social politics in order to grind both personal and political axes. In the adoration of the celebrity aristocracy by the masses, he sees the realisation of de Toqueville's warning of "the tyranny of the majority" and witnesses, for those lower down the food chain, the corruption of the "be all that you can be" meritocracy America promises. If these are soft targets, then the hilariously toe-curling experiences that lead him to take aim are well worth the price of a cocktail. --Fiona Buckland --This text refers to an out of print or unavailable edition of this title.
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It tells the story of Toby Young's time in New York working for Vanity Fair magazine. Toby Young is an interesting, if not particularly attractive, character. He is a very strange mixture of high brow and base instincts coupled with a rather adolescent sense of humour and an amazing ability to offend both intentionally and unintentionally. He seems very self-aware in reflection but is clearly unable to use this self-awareness in the heat of the moment. At times he seems to suffer from 'Roger Rabbit' syndrome - he must say it because it is funny (at least to him) regardless of the consequences.
Toby Young arrives in New York expecting to the presented with a smorgasbord of attractive women bowled over by his English accent, evident (at least to him) intelligence and his celebrity connections (from his position at Vanity Fair). This does not happen. He expects to have a brilliant career at Vanity Fair but he finds the office politics difficult (because he is not a believer) and his sense of humour and capacity of foot in mouth constantly land him in trouble. He becomes obsessed with celebrities but demonstrates a total lack of ability to talk to them in interviews or social situations - a bit of a problem when working for a celebrity magazine. He finds many aspects of life at Vanity Fair distasteful and cannot keep his mouth shut about them leading him inexorably towards the door.
Toby Young comes from the great British tradition of intellectual scepticism (lapsing into cynicism and negativity) and through this filter he is often startlingly perceptive about Vanity Fair, New York and the USA in general. These are the best bits of the book. The chapter on Harvard is very interesting - the lack of intellectual diversity and curiosity appalled him as did the dogmatism and lack of dissent. He is quite perceptive about sexual and office politics although this is somewhat tainted by some of his personal attitudes. The analysis of the popularity of Jane Austen and the New York marriage market is spot on and hilarious; as is the analysis of the extremely hierarchical nature of US society, the so-called meritocracy, and the appalling behaviour in engenders. He is also very good on the shallowness of Vanity Fair and the fashion world in general. Less impressively he has problems with homophobia or rather an inability to notice that people are gay and then saying something ridiculously inappropriate. He also flirts with sexism although some of this is due to a descent into a rather laddish worldview caused by his inability to cope with Vanity Fair and New York.
This is a rather uneven book sometimes very intelligent and perceptive (most of the analysis), at others infantile and rather silly (most of the stuff actually about Toby Young). However, it is a very entertaining book if you can cope with Young's less attractive qualities.
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