The art of the A-list interview

The Extract: We all read interviews with the stars of music and film, but how is the art best practised? A veteran of the A-list tête-à-tête reveals the tricks of the trade, and the tactics that can open up a celeb like an oyster

Mandatory Credit: Photo by Richard Young / Rex Features (780941 ad) Dylan Jones and Jay-Z Armand de Brignac presents 'A Taste of Gold' party hosted by Jay-Z and Dylan Jones, Automat, London, Britain, 02 Jul 2008 (Richard Young / Rex Features)

How do you go about interviewing famous rock stars? What's the best way to prise open a celebrity? The celebrity interview has been so devalued, so diminished by the extraordinary number of people who are now famous that it's often difficult to think of them as anything other than glorified press releases. Years ago, in the golden days of long-form journalism – when any new journalist worth his ink would spend the best part of six months with his subject before finally filing his copy – the celebrity interview was "a very important thing". But now, in a world in which TV's Big Brother has made celebrities out of nobodies, where fame is so homogenised, is conducting an interview still a skill?

Time and restrictions are hugely important to the success rate of the celebrity interview, and if you've only been allotted ten minutes or so, then it's best to go armed simply with 20 quick-fire questions that you can turn into a breezy Q&A (Q: You're trapped with Billie Joe Armstrong, Kylie Minogue and Jake Sheras. With a gun to your head, which one do you have sex with? Q: What colour is Tuesday?).

Conversely, if you can convince your rock star to spend a few days with you, driving through the Hollywood Hills and hanging out at the private views, exclusive concerts and film premieres, then so be it. This is obviously the best way to get to know your subject and, who knows, they might even become your new best friend. It's totally possible to build up a relationship with a celebrity over a period of time, and though they will expect you to treat them with slightly more decorum than they do your bog-standard hack, the access afforded will, on occasion, counteract any sycophancy.

Any decent interview needs a certain amount of compromise; there needs to be a modicum of give and take. Ideally it should be an "I win, you win" situation, with both parties coming away feeling as though their lives have been enriched – if only in a small way. Both parties need to give, while the interviewee needs to be generous with their time and anecdotes.

I once interviewed Gwyneth Paltrow on the set of Shakespeare in Love for the Sunday Times Magazine and she couldn't have been less interested. She gave nothing but monosyllabic answers, and a good impression of someone who'd rather be picking skewers out of her eyeballs than talking to me. For me, it was an enervating experience so, having not got what I needed, I proceeded to interview everyone else on the set: the carpenters, the caterers, the sound guys, her chauffeur, the studio concierge, the make-up girls, the hairdressers – anyone I could find who had anything to do with her. I wasn't looking for a particularly negative story but, given Paltrow's unwillingness to talk to me, I had to get a story somehow. The feedback I got from those around her was not exactly positive. So, in the end she got what she deserved, which is a shame – for her. I'm an easy person to charm, and if she had spent half an hour working her magic on me, no doubt I would have come away thinking Paltrow was a born-again Audrey Hepburn. But she didn't, so I didn't.

Journalists' techniques are fascinating. When AA Gill was interviewed by Lynn Barber, he said it was like being interrogated by Columbo. "Oh, Adrian. Just one thing: you said you were wearing a cummerbund fashioned from yak gut and corduroy on the day in question. Where exactly did you say you bought it?"

As for myself, I don't think I've ever been particularly good at it, even though I've interviewed hundreds of famous people in the past three decades. For years, I made the cardinal error of trying to impress the people in front of me; I wanted them to like me, wanted them to understand how bright I was, and how well-versed I was in their work. I wanted Paul McCartney to think I was the only person who really understood why he was the most talented Beatle, and wanted Keith Richards to think of me as a made man, a groovy young guy who never went to bed and had taken nearly as many drugs as he had. When I met George Bush in Dubai a few years ago, I tried, in the space of two minutes, to impress upon him that my view of the Gulf War was more incisive than anyone else's. I even once tried to contradict Shirley Maclaine's anecdotes about Frank Sinatra.

Fool. Just SHUT UP AND LET THEM TALK. That's what you've got to do. Ask a question, let the famous person start rambling, and then occasionally steer them in the direction of the place you want to end up. My biggest sin has probably been interrupting. You know, just as Siouxsie Sioux was about to tell me who she had been taking crack with last night (that's a joke, by the way; I know that Siouxsie Sioux doesn't take crack), I'd butt in with: "That's great Siouxsie, but tell me about that bit in 'Hong Kong Garden' where…"

My worst ever interview, or at least the one I was least involved with (so it may actually have been my best), was in the mid-Nineties, with Woody Allen in the Dorchester in London. As soon as I shook his hand I started thinking about Frank Sinatra's cock. Why? Well, Woody used to sleep with Mia Farrow, who, years before, used to sleep with Sinatra. So I instantly realised that I was only one female sex organ away from Frank's johnson. This thought preoccupied me all through my chat with Woody. It may, as I say, have been a good thing (at least I didn't keep interrupting him…).

In general, my problem was I couldn't bear for there to be any gaps in the conversation, and in that respect I'm probably like a lot of journalists. But the trick is to let the celebrity fill that space because, in reality, they're just as embarrassed by the silence as you. I know one music journo who is a master at this: a man who thinks nothing of keeping silent for two, three, four minutes after his subject has temporarily stopped talking, thus forcing said rock star to start burbling about nothing in particular. Or, more pertinently, everything in particular.

Sometimes, with celebrities, you are told to adhere to ridiculous restrictions, so you're forced to resort to nonsensical methods. When David Bowie was involved with Tin Machine, he initially refused to do interviews unless the rest of his band were present. This put a lot of people off, but when Tony Parsons interviewed them (at my behest, we were at Arena at the time), he turned the situation to his advantage in the most obvious way: he ignored Bowie – for 45 minutes. In that time he quizzed Bowie's backing band (which is essentially what they were) about stage dynamics, recording techniques and group compositions, until the Thin White Duchess could take it no more. Bowie almost exploded into the conversation, falling over himself to tell Tony the reason for his solo volte-face, and his frustrations with the music industry. By ignoring him, Tony got an extraordinary interview.

Another way to avoid the dark tunnel of product-specific-questions is to confront the interviewee with "the problem". "Hi, Mick. Your PR says that I can only ask questions about the record, but you don't mind talking about your sex life, do you? I mean, how does being gay affect your faith?"

"My PR said that? I don't mind at all. I've got some pictures on my phone of me having sex in church, if you'd like to see them."

Of course, this won't always work but, as a journalist, you must assume that the PR's restrictions are rarely imposed by the stars themselves. And even if they are, you can usually cajole your rock star into talking about the subject – if only in a defensive way. With most stars, there will be this one question that is forever off limits: one question that history has taught you to avoid. With Hugh Grant, it's his experience with Divine Brown; with Madonna, Swept Away (the shocking film directed by her ex-husband, Guy Ritchie); and as for Michael Jackson… Well, you could take your pick.

But you have to ask it. You just have to. Mark Ellen, the very brilliant former editor of Smash Hits, Q, and now The Word, has a fail-safe way of asking the "difficult question". Throughout the interview he will say things like, "Look, I know you won't want to talk about the thing, but I'm going to bring it up later," or "That's all very well, but I must warn you that we're going to have a little bit of a fight later!" Mark said, "It softens them up – lets them know you're going to ask them something they don't especially want to answer. So by the time you get around to it, they're almost relieved."

Once, when I worked on the Observer, we were offered an interview with Eddie Murphy who, at the time, was enjoying a second flush of fame. However, the product Eddie was pushing was a fairly useless rap record, and his Hollywood publicist told us that he would only answer questions relating to this particular project. Not only that, but we were only to be given 40 minutes and it was to be in Los Angeles – not a cheap place to get to at the best of times.

Oh, and the PR had to sit in on the interview. Great! Just about the only thing they didn't demand was copy approval, but it was still a tall order. We ummed and aahed about it, but decided that it was too good an opportunity to miss; we'd have to find someone good enough to exploit the situation. That person, we decided, was Hugh McIlvanney, the greatest sports writer the world has ever known (Scottish, gruff, then already in his sixties, known to enjoy a drink).

Now, we could have picked someone whose job it was to interview celebrities. Or we could have chosen someone famous themselves (Lenny Henry? Stephen Fry?). We thought about a flirty female who could flutter her eyelashes and cross/recross her legs; we even considered the likes of Martin Amis (who was then writing for us). But we decided we needed someone with some specific attributes: who wasn't going to be intimidated (by anyone), who knew nothing about hip-hop (thus eliminating the need for any protracted discussions about inspirations, motivations, choice of producers, etc), who was smart enough to side-step the PR's restrictions, and clever enough to run rings around Eddie himself. And that person was obviously Hugh.

Boy, did we choose the right person. The interview Hugh came back with was remarkable, covering all aspects of the celeb's life: his movies, girlfriends, ambitions, race, politics, sex – the lot. Oh, and there was even stuff about the record (the awful, pitiful record). So how had Hugh done it? The tape of the interview did the rounds in the office for weeks afterwards, and it was almost a masterclass in the art of interviewing difficult, protected and protective celebs. Stupidly, pathetically, I have since lost the tape, but I still remember Hugh's opening question as though he asked it only yesterday.

"So, Eddie. I must say this new record of yours is quite a remarkable thing. I'm not an aficionado of this sort of music at all, but the way in which you paint yourself as the catalyst for this furore around you – the instigator – it strikes me that you are a man totally in charge of your own destiny, if indeed that's what we can call it. How did the making of this record, of all the things you've done, affect the way you see yourself? How does this latest project redefine what you are as a man?" In fact, thinking about it now, the actual question was probably four times as long as that, but the convoluted way in which Hugh approached his subject – and the meandering way in which he asked his question – opened Eddie Murphy up like an oyster. And, for the next two hours, the comedian talked, and talked, and talked, and talked. Which, after all,was the object of the exercise.

And the record? The pathetic rap record Eddie was so keen to puff? It wasn't a hit.

Extracted from 'The Biographical Dictionary of Popular Music' by Dylan Jones, published by Bedford Square Books, available from Amazon and the iBookstore at £7.49 (ebook) and £25 (paperback)