The first thing you see in Toby Young’s small office is a large poster of… Toby Young. The apparent solipsism would not surprise his enemies, who are legion. On the opposite wall hangs a dartboard bearing the boat-race of one such enemy, Martin Amis. But this, after all, is the West London lair of a journalist whose first stab at authorship was a book entitled How To Lose Friends And Alienate People. From one critic it drew the immortal review: “Toby Young is a balding, bug-eyed opportunist with the looks of a beach-ball, the charisma of a glove-puppet, and an ego the size of a Hercules supply plane. And I speak as a friend.”
Strangely, such verdicts are meat and drink to this 43-year-old Londoner. Since graduating from Oxford with his friend (and subsequent editor at The Spectator) Boris Johnson, he has launched the ill-fated Modern Review, been a frequently fired newspaper columnist, an unpopular theatre critic and a much-reviled playwright. But he is best known for the 2001 celebration of his conspicuously unsuccessful career at Vanity Fair magazine: How To Lose Friends, etc is a very funny memoir of his brief stint amid the careerist snobs and frigid offence-takers of glamorous New York – a period in which he became, said one observer, “an ever-present icon of defeat.”
The sequel is called The Sound Of No Hands Clapping: it recounts, with equally toe-curling relish, his humiliating rejection by Hollywood. Where the first book began with a life-changing invitation to join thenprestigious Vanity Fair, then declined to the stage where our right-sized hero was road-testing sex toys for lad mags (on himself), the second sees him fall from promising Brit screenwriter to the man whose phone calls are spurned by the lowliest of the lowly. He finds eventual redemption through a nice English girl and two lovely children. But each book catalogues a string of professional and romantic disasters that would annihilate men of thinner skin.
“I now find myself in the paradoxical position of being a professional failure,” he says, in the deadpan, staccato voice of the writing trade – the voice of people who are always stopping in mid-sentence to decide the exact word. “Mild success would be more damaging to my career than another catastrophic failure. It’s a topsy-turvy sort of career to have. The minute I begin to do quite well, I won’t be able to pay the mortgage. I have to continue to screw up to make a living.”
So where does a likely young man go in search of his next great fuck-up?
“At the moment I’m fantasising about writing, producing and directing a film, in which I might possibly star. That could be a colossal failure on an even bigger scale than I’ve experienced so far.”

“FAILURE IS A TEST OF CHARACTER”
I think failure is much more likely than success to lead to wisdom. The conventional view is that failures are terribly bitter people and that it distorts their whole perception of the world and their place in it; they think of themselves as more sinned against than sinning. But I think the opposite is the case, that people who are very successful see the world through rose-tinted spectacles and are much likely to end up with a distorted picture. People who succeed generally credit themselves with their own well-deserved success, which probably isn’t 100 per cent true. They play down the impact of luck and play up their own hard work and ability. Whereas people who fail, particularly men, simply see it as bad luck. And that’s often true. I think failure enriches you. You’re more likely to be a humane, compassionate person than if you succeed. Most successful people go through this developmental arc in which they come to realise, by the end of their lives, that money and fame and status aren’t the be-all and end-all of existence. The good thing about being a failure is you realise this straight away.

“AMERICANS RESPECT SUCCESS, THE BRITISH TAKE THE PISS”
I think at the heart of American society is what Plato would call a Noble Lie, a salutary myth. Which is that America is the land of opportunity and that anyone who is willing to put in the hours can succeed. And the corollary is that people who fail simply haven’t tried hard enough. Both failure and success are thought to be well-deserved, and as a result the Americans respect successful people and loathe and detest failures. Almost the opposite myth prevails in Britain, which is that it’s not what you know, it’s who you know. That your life chances are entirely dictated by the circumstances of your birth and no amount of hard work will overcome that. People here think that successful people, the ruling class, are just members of the lucky sperm club. I think we’re generally suspicious of successful people. It’s the ‘tall poppy syndrome’. And, not being terribly successful, I have a lot of time for the tall poppy syndrome. Think how much more insufferable Posh and Becks would be if, in addition to having all that fame and money, they were universally respected.

“SCANDAL IS THE REVENGE OF THE MOB”
The people who voraciously consume tabloid gossip have a great deal in common with the old ladies who used to bring their knitting down to the guillotine and watch aristocrats have their heads lopped off in the French Revolution. One of the reasons the public enjoy seeing celebrities brought down isn’t merely because it satisfies their sadistic cravings; it’s because it makes them feel that they are the real repository of the kudos the celebrity enjoys, that without the public’s approval, they can’t continue to lead the successful lives they’ve been leading. Most celebrities depend on popularity to open a movie, sell a record or garner ratings for a TV show. They depend upon being liked. Often times they seem to forget that and imagine that they’re gods walking among us, who are just entitled to these extraordinary perks. So it’s a salutary reminder when they get embroiled in a scandal and they’re not nearly so likeable, that their power is only held on trust and can be taken away at any time. And that makes ordinary people feel powerful.

“IT’S BETTER TO HAVE LOVED AND LOST, BUT THE SAME DOES NOT GO FOR FAME”
I recently saw a once-famous pop star talking about how hard it was, just waiting for a bus. People were so cruel, they would point and laugh and jostle him. People think there is a correlation between fame and status and that’s why they crave fame. But it’s not actually true, because some people are famous has-beens who don’t have any status. Certain types of fame have the opposite effect. You can be famous for being forgotten about, which is paradoxical. The Simon Dee syndrome.

“LIMOUSINE LIBERALS SHOULD READ TOM WOLFE”
I think in New York there is a connection between status and paying lip service to certain liberal ideas, and nine times out of ten the reason prominent New Yorkers espouse liberal values is to advertise their membership of the elite. It’s also a way of making themselves look a little less shallow, that they care about the wider society, that they’re not just interested in getting a higher visibility booth at the Four Seasons Restaurant. It’s true of Hollywood too. The thing that baffles me about contemporary limousine liberals is that they can carry on as if Tom Wolfe had never coined the phrase ‘radical chic’, in that marvellous essay about attending the benefit for the Black Panthers at Leonard and Felicia Bernstein’s apartment. He absolutely skewered that whole class.

“JOURNALISM IS LIKE DROPPING STONES DOWN A WELL – AND NOT EVEN HEARING A PLOP”
Being a successful columnist produces no real long-term career satisfaction. All journalism, no matter how prominently displayed in the paper, is completely forgotten the next day. You never get a sense of cumulative achievement. You never get that job satisfaction you imagine architects get, when they step back to look at the finished building and think ‘A-ha, a monument! In 100 years’ time people will know that I walked the earth!’ What’s the journalistic equivalent to that? There isn’t one.

“STUDY THE LOCAL CULTURE”
About six months after I arrived at Vanity Fair I discovered that my office workmate had a birthday coming up, so I thought it would be amusing to hire a stripper-gram. I persuaded the fashion director of the magazine to let me use this large room, the fashion department, to stage this event. The stripper arrived in the building, head-to-toe in stone-washed denim, and I lured my friend to the fashion department on some spurious pretext and the stripper began strutting her stuff. She’d brought along a boogie box and was playing Michael Jackson’s Beat It as she was performing her striptease; she’d got down to her leopard-skin kickers and was waving her breasts in my colleague’s face when there was a knock at the door. I killed the music, and it was the editor’s three-year-old daughter: ‘Can I see the fashion department?’ Everyone held their breath. ‘Not now, sweetie. Can you come back in ten minutes?’ She toddled off, we closed the door, put the music back on, the stripper started again. Five minutes later there was another knock on the door and this time it was three little girls. It turned out that in my wisdom I had arranged for a stripper-gram to come to the Vanity Fair office on something called Take Our Daughters To Work Day, which was a national institution I knew nothing about, whereby these hard-working women bring their daughters to see what Mommy does all day. And of course the only place little girls wanted to see was the fashion department. So there I was stuck in this room with this stripper from central casting and an army of little girls accompanied by their hatchet-faced moms, waiting outside the door. We smuggled her out and I swore everyone to secrecy but within 24 hours I was known throughout the building as ‘that English chump who hired the stripper-gram on Take Our Daughters To Work Day’.”

“NEW YORK WOMEN ARE PURITANS”
I don’t think English women will ever be as po-faced or prudish as their American counterparts. In many ways New York women of marriageable age have a 19th century world view: it’s taboo to sleep with anyone on the first date. You have to go through this elaborate courtship ritual to get to first base. Unless they think you’re some random guy who’s only in town for one night. In fact when I went out on the pull with my mates we would always pretend that we had a plane to catch back to London at 6am. They would be very surprised when they saw us at the Gucci party the following week. Encountering a sexual culture so different from ours meant that I had to go back to the drawing board. None of my tried-and-tested techniques, such as pouring vodka down a woman’s throat until she was on the verge of passing out, cut any ice in New York. People talk about the incredible sexual opportunities awaiting Londoners in New York. They say it’s like being a movie star if you have an English accent. I really didn’t find this to be the case. When New York women hear an English accent they think, ‘Low income, small apartment, alcohol problem.’ And nine times out of ten they’re absolutely right.

“THE PRAM IN THE HALL IS NOT THE ENEMY OF GOOD ART”
I know that Cyril Connolly said it was, but different writers respond in different ways. The arc my character follows in The Sound Of No Hands Clapping is in thinking, initially, that having children and being married is an impediment to success as a writer. That the time you feel obliged to spend with your wife and children encroaches on the time you should be spending writing a book or a screenplay. But at the end of the book I change my mind about that and realise that without the order and stability of family life, I wouldn’t be able to write anything at all. I’d just be a hopeless drunk. And far from being an impediment to my career, without my wife I wouldn’t have a career.

“PARENTHOOD IS LIKE A 12-STEP PROGRAMME”
You simply can’t stay out ’til 4 o’clock in the morning drinking and taking drugs if you know that your daughter’s two-year-old face is going to be pressed up against yours at 6 am, demanding to play hide-and-seek.