How to Lose Friends and Make a Movie

“You see those extras?” said the producer, indicating a group of nubile young women standing a few feet away. “They’re yours for the asking. Just point to the one you like and I’ll have her sent to your room.”

This was in the summer of 2007, and we were on the roof of Soho House in New York shooting a scene from How to Lose Friends & Alienate People. I was actually staying at Soho House, so from a purely practical point of view it would have been relatively easy to dispatch one of these young women to my room. But was he being serious?

True, I had written the book the film is based on—a memoir about my failure to take Manhattan as a glossy magazine journalist in the ’90s—but that isn’t normally a perk extended to authors. There’s a saying in Hollywood that being a writer on the set of your movie is like being a husband in a delivery room—and I hadn’t even written the screenplay. I was like the husband’s best friend in the delivery room. It seemed unlikely that any of the extras would want to sleep with me.

I had expected to be over the moon on finding myself in this situation—My book is being made into a film!—but instead I was wracked by doubt. Is that really Kirsten Dunst standing over there? And is that person standing next to her really Simon Pegg? It can’t be true. I’ve noticed the same incredulous expression on the faces of Oscar winners. Me? An Academy Award winner? It must be a mistake. At any second a little boy in the audience is going to leap up and point out that the emperor isn’t wearing any clothes.

One of the reasons it felt so unreal is because it had been such a struggle to get to this point. I had been hoping against hope that the book would be turned into a film ever since it had been optioned by an independent production company five years earlier, but there was never a single moment when I thought, “This is really going to happen.” On the contrary, there were just lots of occasions when I thought, “This is never going to happen.”

For instance, there was the time I opened a copy of Variety and saw the following headline: “FilmFour’s deep-sixed.” That is to say, the British production company I had struck a deal with had been closed down. It would eventually be resurrected, but at the time it didn’t look good.

Then there was the phone call I got from Stephen Woolley, one of the film’s two producers. Stephen is probably the most successful independent filmmaker in the U.K., having produced Interview With the Vampire, Scandal and The Crying Game, among other films, so if he couldn’t get it off the ground, no one could. Yet he told me that every single writer he had sent the book to in the hope of persuading them to adapt it had turned it down.

My original plan was to adapt it myself—and Stephen had initially embraced this idea. At my first meeting with him, back when he was still angling for the job, he told me I had written the Catch-22 of my generation: “You’re such a brilliant writer, you’re clearly the guy to adapt it for the big screen.”

Not surprisingly, he changed his tune as soon as he got the gig. Actually, that’s a little unfair. Strictly speaking, he didn’t change his mind until he read the 35-page treatment I submitted, but I like to think he never had any intention of getting me to do it in the first place.

For some reason, Stephen kept me involved in the development of the film, first as an associate producer and then bumping me up to co-producer. Did he hold with Lyndon Johnson’s maxim that it was better to have someone like me inside the tent pissing out than outside the tent pissing in? That was probably part of it. In addition, he may have thought I had something to contribute, not least because the book in question was a memoir. After all, who better to advise on whether the film’s details were right than the person whose story it was? In purely practical terms, I was a useful guy to have around.

I had heard lots of stories about “development hell,” but my experience was anything but. Stephen eventually hired a writer named Peter Straughan, and the three of us spent 18 months working on the script. Both Stephen and Peter were very author-friendly, far more so than the vast majority of people in “the business,” and I tried my best not to abuse that goodwill. I was determined not to fall out with them, as I had with so many of the other people I’d been professionally mixed up with. I didn’t want my involvement in the film to echo the events being depicted onscreen.

It all went pear-shaped in the end, of course—and I blame the director. At first, Bob Weide and I got on pretty well. His main claim to fame was that he’d directed about half the episodes of Curb Your Enthusiasm, one of my all-time favorite sitcoms, and I thought that anyone good enough for Larry David was good enough for me. He had other things going for him, too. Shortly after he’d been appointed, I was in L.A. promoting the American publication of The Sound of No Hands Clapping—the sequel to How to Lose Friends—and he invited me to the Playboy Mansion. It was Hugh Hefner’s annual Fourth of July party and Bob was on the guest list—not a bad way to kick off a relationship. We’re going to get on famously, I thought.

However, when the film finally went into production in June of 2007, things started to deteriorate. On my first visit to the set, about a week after principal photography had begun, I insisted on taking Bob to one side and giving him some notes. I wasn’t happy with how he was directing a particular scene—I didn’t think he had fully grasped what was supposed to be happening at this point in the story—and thought he would appreciate a bit of elucidation. He was remarkably good-humored about it, but even someone as thick-skinned as me could tell this was an unwelcome distraction from the business in hand.

After a couple more visits, on one of which I antagonized Kirsten Dunst by giving her a “performance note,” I sent Bob a lengthy e-mail telling him that every time I dropped in on the set, I became more and more anxious about the fate of the film, and he sent a five-word reply: ‘Very easy solution to this.’ In other words, stay the fuck away. I resented this at the time, but it was good advice. Up until this point, Stephen had consulted me about all the key decisions, including whom to cast as the male lead, and now that Bob was in sole charge, I couldn’t cope with the loss of control. I started to panic, and whenever I visited the set, I began to act like one of those crazy airline passengers who becomes convinced that the plane’s going to crash and wants to wrest control from the pilot. Little wonder Bob didn’t want me around.

After six weeks of shooting in London, the production crew moved to New York, and that’s where I caught up with them again, on the roof of Soho House. I was ostensibly there to shoot my “cameo”—a one-second glimpse of my face at a party—but the real reason was that I simply couldn’t resist the opportunity to return to America in triumph. I had spent five years trying to take Manhattan and gone back to London with the stench of failure hanging about me. Now, seven years later, I was back, co-producing the film based on the book I’d written about that same series of disasters. To quote Robert Duvall in Apocalypse Now, it smelt like victory.

“I’ll take that one over there in the white dress,” I said, pointing to a beautiful Hispanic girl. “I’m in room 15.”

“I’m only joking,” said Stephen Woolley.

“So am I. My wife’s asleep in my hotel room. I’m a happily married man with three children.”

“I still can’t get my head around that. I find it so hard to believe.”

Me, too. You know where you are with failure—it has an air of solidity about it. But success feels fleeting and insubstantial—a mirage that might vanish at any moment. Where’s that little boy in the audience? And why hasn’t he stood up yet? It’s only a matter of time.

How to Lose Friends & Alienate People opens on Oct. 3.

editorial@observer.com

How to Lose Friends and Make a Movie