Interview: Simon Astaire

The showbusiness agent seems to have it all — wealth, fame, celebrity girlfriends. But his schooldays at Harrow still blight his life.


Simon Astaire with close friend, Nancy Dell’Olio. Astaire has dated Tara Palmer-Tomkinson and Ulrika Jonsson

Simon Astaire with close friend, Nancy Dell’Olio. Astaire has dated Tara Palmer-Tomkinson and Ulrika Jonsson

You are a celebrity agent and media adviser. You spend most of your waking moments in the company of the kind of models, actresses and starlets at home in the pages of Hello! magazine. You have a string of glamorous girlfriends, from society girl Tara Palmer-Tomkinson to television presenter Ulrika Jonsson. You fly first class between London and Los Angeles every month, and your clients include Oscar-winning actress Rachel Weisz and the Queen's cousin Lady Gabriella Windsor. You were best man at Sting's wedding to Trudi Styler.

But still you are not happy. What do you do? Go into therapy of course.

That was exactly what Simon Astaire did when he realised that his glitzy lifestyle was leaving him empty and unfulfilled. And the more the 47-year-old showbusiness guru talked to his therapist, the more he realised, he says, "that virtually every road reverted back to my schooldays". We are not talking about a local comprehensive, however.

Astaire, London-born, is the son of stockbroker Edgar Astaire, who is chairman of the Jewish Memorial Council, and interior designer Lesley Jacklin. He was educated at Wellesley House in Kent and Harrow School - two pillars of the English public school system. And the experience of being a lonely Jewish schoolboy at his prep school and then at Harrow has, he believes, led to his present disatisfaction with his life, and - more importantly - his inability to commit to relationships with a series of beautiful women.
As he and the therapist began to explore his experiences at school, Astaire began to write things down.

And it was just too painful, the deeper I went. So I decided to create this character who could live a life similar to mine, and perhaps make decisions which I didn't make at the time... it was just a story of a boy being sent away to school. It came out very easily. I purged what I had gone through by getting up every morning and writing for two hours. In six months, I had a book."

The result, slightly to Astaire's astonishment, is Private Privilege, his first novel, snapped up by the renowned publisher Naim Atallah just 10 hours after receiving the manuscript, and is now being made into a film. It has to be said that Atallah's enthusiasm may have resulted in a rushed editing process, since the book is littered with syntactical errors and the dialogue is at times woefully wooden. But the central character, Samuel Alexander, whose prep and public school experiences are a close mirror of Astaire's, succeeds in attracting the reader's sympathy.

Astaire says he is not ready to say how closely autobiographical the book is. But some episodes are shot through with hurtful realism, notably the antisemitism suffered by Alexander and, he says, by Astaire himself. In the book, he writes: "My father kept a kosher home and when he sent me away to a place that had very few Jews in its history, he merely insisted to the school that I didn't eat pork. And so every Sunday when the whole school was served pork sausage and beans, I had to take the slow lonely walk to the kitchen, past the long table of whispering boys, to pick up my beef sausages."

Since the publication of the book, Astaire has received scores of emails from contemporaries at Harrow who shared the misery and loneliness of being a public schoolboy. It was not something, he says, which could ever have been talked about when they were actually at school - it would have been seen as a sign of weakness.

"When I was sent to prep school I cried on the train and I cried in bed at night. But I learned at a very impressionable age not to open up my emotions. You were just told that you don't behave like that." School friendships, he says, were essentially shallow. "It was a bit like when I dated women: I didn't think how I was treating them, it was all about moving on... there was never a time when I just sat and contemplated what was happening."

He agrees that he thinks of himself as "damaged goods. Yes, I feel that I'm injured. It's like a wound and it hasn't healed - but I'm putting it right now."

Within weeks of arriving at school in Kent, Astaire found a note in his desk. "It told me to go home because I was Jewish. I remember feeling amazed by it. Then it grew, and I recognised that I was an outsider. Not only was I dealing with being homesick and leaving the comforts of my cosmopolitan life, I was also dealing with that."

Since his father wanted him to be barmitzvah, a rabbi was despatched each week to teach him at Harrow. "And also - this is really coming out now - when you're sent away to school, there's a big rigmarole about going away, and saying goodbye - and then a week later you're yanked out of school for Rosh Hashanah or Yom Kippur, which doesn't mean anything to you. So you're immediately seen as an outsider, because you're dragged away from school to go home."

And yet, Astaire says, he is comfortable today with his Jewish identity. "Being involved in showbusiness at a very young age has helped me, by default, feel very comfortable with my Jewishness. I was an English public schoolboy with a posh accent and that meant I could talk to whoever.

"One thing public school does is it allows you to talk to lots of different people. You can communicate. So I had that... and then I had the Jewish side. When I left school I knew my father wasn't going to support me financially so I saw this advertisement for a telephonist in the Evening Standard. So I thought, I've got a good voice, it's a theatrical agency, so I applied for it, and I got it. But after four weeks I was so bored. I knew that if I just left, my father would look at it as laziness, so I had to get fired. And that morning a producer rang up and he said: ‘Could I speak to the agent of an actor you represent? We've offered £50,000 and I've been trying to get hold of the agent for two weeks. Is he [the actor] going to do the job? I can't get an answer. If I don't hear by six o'clock, it's over.'"

The producer rang back at six and asked if Astaire had been able to get hold of the agent. "I said no. In fact I had tried, but I told him, no. And he said, well, what's going to happen? And I said, well, he won't do it for less than £100,000. So the producer said, are you out of your mind? You tell the agent and the actor they can find another job, I'm going to get someone else. And he slammed down the phone.

"I went home that night convinced I'd got fired. But the next morning I was greeted by a line of applauding staff. ‘Never in my life,' said the head of the agency, ‘have I seen the initiative you have taken. You will be made head of young artists.'" For, of course, Astaire's chutzpah had succeeded in getting the £100,000 for the actor.

Four weeks later he was headhunted by the talent agency, International Creative Management (ICM), the biggest in the world. "The moral," says Astaire, "is that I saw something... by having certain confidence - which was intrinsically part of my heritage, and which made my father and my uncle so successful. And I met more and more people within the business, and they had the same sort of feel as me. So I was able to be posh, and yet at the same time to be a nice Jewish boy. It's not all bad."

One obvious question remains - in all his long history of glamorous girlfriends, has he ever been out with a Jewish woman? There is a momentary pause. "No," he says, with some amusement. "I'm attracted to Jewish women, but I've never had a Jewish girlfriend. I was keen on one but I don't think she believed that I was sincere or genuine."

Private Privilege is published by Quartet Books, priced £15

    Last updated: 2:59pm, August 28 2014