How To Lose Friends And Alienate People: A Memoir

The top five things I hate about Toby Young's book:
5. The writing.
This book was seriously dull. His anecdotes and his writing lacked any kind of insightful spark. With access to Vanity Fair bigwigs and Candace Bushnell's inner circle, you'd think he would have more to report than the fact that they all hated him.
4. Any sentence Young wrote about himself.
They usually started out as self-deprecating and quickly eased themselves in self-pitying. "Then I got fired again haha...I'm so underappreciated." "
3. His conclusions about the nature of America and New York City.
While I appreciated that Young did his research and made interesting statements based on Alexis de Tocqueville's Democracy in America, I was astounded that he was deluded enough to believe that Americans did not appreciate his boorish and asinine sense of humor because they are too uptight and PC. What made him think that British people were more accepting of his sense of humor if the entire book was about him trying to escape his failure in Britain?
2. His attitude toward women.
To say the least, I was completely repulsed by Young's treatment of women throughout the book. He is a skeez who judges women only on their looks (bonus points are given to women who make a living on their looks), yet he constantly whines that women are shallow for turning him down due to his baldness, mediocre looks, lack of gainful employment, or any combination of these charming factors. Ugh.
1. The fact that I waded through the whole thing despite reasons 2-5.
I must be a masochist.

I gave the book as a gift to my daughter who is in NY media/publication. She liked it as she could relate to events and characters mentioned in the book.

I have not read it myself.

OK - I really enjoyed this book. At its best Toby Young's "How to Lose Friends & Alienate People" is utterly laugh out loud funny. I honestly can't remember a book where I have literally cracked up so many times. (Colbert's book made me laugh too - but not this kind of out loud public sniggering on the train that made others notice me in an embarrassing way). The best bits are when he takes on (and names names) the peacock culture of the big Conde Nast culture mags and their ab fab brass and human adornments. He's also justifiably famous for his celebrity party antics (which specialize in gate crashing and then being ejected by bouncers). Time and again he blithely justifies himself stepping way out over the line and getting himself into classic scrapes - lapses of taste and judgment - and humiliating jams of a dizzying variety. An incredibly high percentage of these episodes are just "rilly rilly" funny (I'm an American and that's how I say it - in alliterative Toby lit). His evolving envious relationships with Alex De Silva and Graydon Carter are recurrent themes in the narrative; as well as his literary, social, and sexual ambitions. His madcap ways, clever use of recurrent themes, and deft comic timing are a big part of the comic goodness. The fact that Toby's a great writer doesn't hurt either.

This comic achievement makes me more tolerant of the parts that weren't so good... Like the parts where Toby's sour grapes about not getting laid makes him expound pedantically on the shallowness of the New York glitterati maidens he chooses to pursue. I mean - who's really being shallow here? Then there's his plunge into full blown alcoholism... There are comic moments but much of it is actually genuinely tragic. In the latter chapters when Mr. Young gets introspective about his self-destructive streak he redeems himself somewhat by showing us some self awareness and getting a handle on both his alcoholism and his romantic shallowness - but it's a bit too little too late. It's not that Toby's bad boy antics are too risque. It's that his bitterness and sour grapes over his lack of temporal and carnal success colors his philosophical ramblings - giving them an aspect of priggish self indulgence that is ... well ... alienating. You'll see lots of negative reviews of people who just hate him for it and it's easy to see where they're coming from.

Will you love or hate this book? That depends on how interested you are in the NYC literati glitterati world and how much fun you'll have seeing a drunken party boy lurch about in it breaking all the rules and stepping on all the toes. Personally - my life shares too many details in common for me not to love this book. But it is not an unconditional love. I can't help feeling that Mr. Young is just too self involved and immature to use as much philosophy as he does. Maybe that's just my American patriotism talking (he's skewering American culture when he's doing this) - but that's how I feel. Thus the 4 stars. Reading over what I just wrote it sounds pretty negative - so why do I only dock it one star? Toby is a comic genius. That's pretty rare. This book might not be entertainment perfection but it's a wild ride, a trip down the rabbit hole, a view into a fully realized world, and - in the end - a real hoot.

Follow-up 12/08: The philosophical parts of this book - the essays about de Tocqueville and how the concept of "Meritocracy" (a term invented by Toby Young's father) is used in the US at a diversion to legitimize gross reinforced economic inequalities - has worked it's way into my consciousness. I see evidence all over and I must now grudgingly acknowledge the argument's merit. I think I discounted it for so long because it's in what is otherwise a funny book. I actually think this is a pretty significant book of social criticism; although I still think Toby is whining about the shallowness of those elite babes.

I picked this up because the title caught my eye. It was actually quite good, funny and well-written, and it held my attention. I think Toby Young's assessment of the American meritocracy was accurate and spot-on. I got a kick out of the behind-the-scenes glimpses of Vanity Fair and Graydon Carter -- I don't want to spoil it, but I think Toby got the last laugh. Highly recommended.

I don't normally give memoirs the time of day, but I managed to get through this one without any major difficulty. It was funny at times as the author describes his downward spiral as a British import to Manhattan trying to pursue a life of fame and relative fortune. However, it's hard to really identify or sympathize with a character/real person who keeps making such obvious and colossal gaffes and screw-ups. Why would it surprise him that hiring a stripper to come into the office for some guy's birthday would offend women? Why would it surprise him that calling up an Asian-themed clothing company and pretending to order Chinese food would offend an Asian person? His big revelation at the end of the book (spoiler alert) that he just *MIGHT* be his own worst enemy was pretty glaringly obvious in a book where you spend half the time rolling your eyes at his choices and the other half mentally screaming "Not again!" and wanting to step inside the book to kick his butt into shape.

One of the reasons I don't read memoirs is that they always seem to be tryng to "teach" the reader something, and I like to read primarily for entertainment. All this book really "teaches" you is not to squander opportunities when they're handed to you on a silver platter, which is something that most people have enough common sense to already know on their own. This guy gets $100,000.00 a year to write for VANITY FAIR, an opportunity (and a salary) that most people would kill for, and he flushes it down the toilet. This book is basically you watching a toilet flush, for 300 pages. And he spends way too much time moralizing and rationalizing. As he tells his friend "Alex De Silva" (His name was changed; the Alex De Silva listed on IMDB.com definitely isn't the same guy.) he'd feel a whole lot differently about life in New York if things had worked out the other way. If he HAD made the most of what he was lucky to have been given and if he HAD succeeded at Vanity Fair, he'd be singing a very different tune. There'd be less raging about the "American meritocracy" system and more kissing of Graydon Carter's rear.

Bottom line: don't bother.