I want to be Larry David

What's the difference between an obsessive fan and a stalker? Well, I've never loitered outside Larry David's house and my name isn't Rupert Pupkin, but if I was him I'd still make sure my door was locked at night. It's not simply that I know so much about him I'd choose him as my Mastermind special subject. It's not even that I daydream about meeting him and am convinced that we'd get on like a house on fire. No, I actually want to be Larry David.

On the face of it, this might not seem like such a weird admission. After all, as the co-creator of Seinfeld, the most successful sitcom of all time, this 59-year-old comedy tsar has a personal fortune in excess of $200m. The fifth season of his current show, Curb Your Enthusiasm, is about to be released on DVD and in a recent poll in which comedy professionals were asked to name their favourite comedians of all time he was ranked 23rd. He is, by any measure, a hugely successful man - a titan of the media-industrial complex.

Yet, as anyone who knows anything about him could tell you, he's not a happy camper. He's not unhappy, exactly, but he's not a well-adjusted person either. He has anger-management issues and that's a big problem for a man who's capable of being driven round the bend by overzealous shop assistants. He modelled the character of George Costanza in Seinfeld on himself and in Curb Your Enthusiasm he actually plays a character called "Larry David" who, while clearly an exaggerated version of himself - dyspeptic, argumentative, prone to gaffes - is not a million miles from the truth. To top it all, he looks like a cross between Mr Burns and Krusty the Clown.

Might it be possible to enjoy Larry David's assets without sharing his neuroses? Highly unlikely. His humour is inextricably bound up with his life. The cliché about comedy writers being socially awkward curmudgeons who have troubled relationships with their mothers seems to apply in his case. When asked by an interviewer how he came up with the idea for "The Contest", the notorious Seinfeld episode in which George is caught masturbating by his mother, his explanation was simple: "You write about what you know." His comic sensibility is very different from Jerry Seinfeld's, whose humour is generally categorized as "observational" and whose jokes begin, (omega) "Did you ever notice?" Larry David isn't interested in the world; his source material is himself. He doesn't tell jokes; he is the joke.

So why on earth would anyone want to be him?

Well, the truth is, it's not so much that I want to be him, as I already am him. When I watched my first ever episode of Seinfeld I experienced a jaw-dropping jolt of recognition: George Costanza, c'est moi. It wasn't simply a matter of the uncanny physical resemblance - as played by Jason Alexander, George is short, fat and bald - as the fact that he was such a monumental loser.

For instance, George is so bad at picking up girls, in one episode he decides to do the opposite of whatever it is he'd normally do - and before long he's beating them off with a stick. I, too, have been reduced to desperate measures in my efforts to impress the opposite sex - though without any corresponding success. On one occasion I even dressed up as a woman and went on a whistle-stop tour of a dozen lesbian clubs in the hope of picking up a "lipstick lesbian". I ended up being chased through the streets at 3am by a woman who resembled an East German shot-putter.

Another example: in an episode called "The Red Dot", George buys a woman a cashmere sweater as a thank-you present for getting him a job at her company. Unfortunately, the gesture backfires when she discovers a small red dot on the sweater, revealing that it's a second. This reminded me of the time I tried to convince a girl who'd just dumped me that I was a "classy" guy by giving her a Gucci watch. She was initially impressed - until she discovered it was a fake.

"I just can't believe you'd do something like that," she said, handing it back to me. "Are you surprised I broke up with you?"

Of course, reflecting on this now, I realise I probably wasn't alone in seeing something of myself in George. At one stage, Seinfeld was the highest-rated show on American television and that must partly have been because millions of underachieving, middle-aged, bald guys experienced the same beer bottle-dropping moment when they first set eyes on Jason Alexander. The sitcom was often acclaimed as "a show about nothing", but in fact it was a show about George - or, rather, Larry. And the reason it was so popular is because there's a little bit of Larry in all of us.

Still, I don't suppose many of the show's fans identified as strongly with George as I did. It's embarrassing to admit, but I became so obsessed with Seinfeld that it played a big part in my decision to move to New York in the mid-1990s. I was fed up with trying to track it down in the wee small hours of the morning on BBC2. I wanted to see each new episode, freshly minted, on NBC. I also harboured fantasies of bumping into Larry David at the local coffee shop - or, if not him, someone very like him. Seinfeld tapped into my fantasy of New York as this incredibly sophisticated city where everyone was smart and cynical and had a wisecrack at the ready.

I quickly realised that almost no New Yorkers were as funny as the cast of Seinfeld, but at least girls at parties knew what I was talking about when I introduced myself as "the real George Costanza" (which was my idea of a great pick-up line). For the next few years, whenever I was in a really awkward spot, I found myself asking, "What would George do?" Take the time I briefly attracted the attention of a stalker. She'd read an article I'd written for a US magazine about internet dating and decided that I was the man for her. She winkled my email address out of the magazine's editor and started bombarding me with over 100 emails a day, each one containing a mobile phone number and threatening me with unspeakable violence if I didn't dial it. After several weeks of this I began to dread switching my computer on in the morning for fear of what I'd find in my inbox.

What would George do?

I decided to call her and ask her out on a date.

To my astonishment, the girl who was waiting at the bar of the Plaza Hotel that evening carrying a red carnation turned out to be an absolute knockout. Was this some appalling prank being played on me by one of my friends? There was only one way to find out. I marched up and introduced myself.

"You're Toby Young?" she said, seeming slightly taken aback.

"Yes."

"The guy I've been emailing, like, 100 times a day for the past month?"

"Yes, that's me."

"I've made a terrible mistake," she said and then walked out of the bar.

Needless to say, I never heard from her again - and this in spite of the fact that I started emailing her 100 times a day.

In terms of George-like behaviour, however, this was nothing compared to the time I finally persuaded a girl to go out with me - and immediately decided to propose to her. It was 31 December, 1999, and I'd managed to convince a friend of mine in the diamond district to get me a trade discount on a ring. Not only that, but he'd agreed to let me have it on a sale-or-return basis - which was just as well since she ended up turning me down.

As I was putting the ring back in my pocket, she asked if she could take another look at it.

Why not?

"I know this is really cheeky," she said, rolling it between her fingers, "but how much did it cost?"

I was about to tell her the truth - my friend had let me have it for the bargain-basement price of $1,000 - when it dawned on me that there was nothing to prevent me exaggerating a little bit. After all, she was going to give it straight back and I was going to return it to my friend. There was no way on earth she'd ever find out the ring's real cost.

What would George do?

"Thirty-five thousand dollars," I said.

Her eyes became like saucers.

At this point, if we'd actually been in a Seinfeld episode, she would have slipped the ring on her finger, held it up to the light and said, "Run that proposal by me one more time." I would have then had to spend the next hour trying to persuade her not to marry me in a desperate attempt to get the ring back.

In fact, after a brief consideration of what might have been, she did hand it back, though three months later, when I proposed again, it may have been the thought of that $35,000 sparkler that prompted her to say yes. If so, she was disappointed. By then, I'd taken the precaution of returning it to my friend.

As Larry David's self-appointed number-one fan, I watched the first episode of Curb Your Enthusiasm as it was broadcast - 17 October, 1999, the date of my 36th birthday. I was amazed to discover that, like me, he was now ensconced in a relationship. Instead of making jokes about the miseries of being single, he was now trying to navigate the battlefield of married life - and stepping on a landmine roughly every 30 seconds. The similarities between the problems in his relationship and mine were spooky. Like me, he seemed to be engaged in an endless round of territorial disputes and, like me, his partner kept getting the better of him. Indeed, at one point in the first episode, Larry gets into hot water when he compares his wife to Hitler. This was eerily reminiscent of a similar incident in which I likened my relationship with Caroline to the conflict between Egypt and Israel, casting myself as Anwar Sadat and Caroline as Menachem Begin. What was going on? Did Larry have a webcam trained on my New York bed-sit? And given how much of his material was clearly based on my life, where was my share of that $200m jackpot?

That clinched it. If this guy Larry David could transform his sad and pathetic life into a comic goldmine, it was high time I followed suit. I decided to write a comic memoir about my misadventures in Manhattan and, two years later, How to Lose Friends & Alienate People became a bestseller. (One critic described it as "loser lit".) Not surprisingly, my career as a professional failure hasn't proved nearly as lucrative as Larry's, but our lives continue to overlap. It's just been announced that How to Lose Friends is being turned into a film and the man who's going direct it is Robert Weide, who happens to have directed half the episodes of Curb Your Enthusiasm.

"A friend of mine once called Larry David 'The Everyman that no man wants to be,'" Weide has said. "The same would apply to Toby. The thinking seems to be that if I can help make a lovable antihero out of Larry David, perhaps I can do the same for Toby."

So just why are Curb and Seinfeld so good?

The conventional wisdom is that it's because Larry has always refused to compromise. On Seinfeld, his intransigence in the face of network pressure was legendary. He actually had cast-and-crew jackets made up bearing the legend "No Hugging, No Learning" - a reference to the feel-good sitcoms he was trying to get away from - and that quickly became the mantra in the Seinfeld writing room.

No doubt Larry's hatred of sentimentality is one of the reasons his work is so good, but it's not the whole of the story. The characters in Seinfeld may not be your typical, warm-and-fuzzy stereotypes, but they form a tight-knit unit nevertheless. They are all, in some sense, alienated from society, yet they share the bond of the dispossessed. In their own, twisted way, the four main characters exude a powerful sense of community. One of the reasons I felt such a connection with George is because I, too, felt like an outsider throughout my 20s and 30s. That's why people grow so attached to their favourite television shows - because the characters become like a second family to them. The difference between Seinfeld and other, lesser sitcoms, isn't that it was darker, edgier, meaner - though it was all of those things. It was that the warmth between the characters was genuine as opposed to tricked-up. There was something completely authentic about the fellow feeling that existed among this group of curmudgeons. Seinfeld was the real Friends.

The appeal of Curb Your Enthusiasm is harder to pinpoint. In Season Four of Seinfeld, Kramer sets off to make his fortune in LA and, in a sense, Curb is about the continuing adventures of George after he's moved to the West Coast and actually made it. What we're witnessing is George cut off from his support network - an unbalanced, disorientated George who finds success even harder to cope with than failure.

In theory, this should have a strong whiff of bad faith about it. After all, just how miserable can a guy with $200m be? In a bad-tempered essay in The New Republic, a critic named Lee Siegel complained that, in asking us to sympathise with a put-upon tycoon, Curb was breaking one of the fundamental rules of the genre: "Comedy used to be about the iron, the ancient Greek word for the original little guy, who appeared in classical comedy puncturing the... pretensions of the big guy. It set the spiritual order right by turning the social order upside down. But Larry David has returned the social order to its upright position by standing comedy on its head. For perhaps the first time in the history of the genre, he has put comedy on the side of the big guy."

I have some sympathy with this point of view - like Lee Siegel, I don't have $200 million - but, in spite of this, Curb works. I think this is because it adheres to an even more important rule, namely, that the universe the protagonist finds himself in must be unremittingly hostile. (In this respect Curb has a lot in common with Fawlty Towers - Larry David is the Basil Fawlty of the Billionaire Boys Club.) Larry may spend his time "living in a luxurious house, eating at expensive restaurants, hanging with the rich and the famous, rambling around Santa Monica and Malibu and Beverly Hills", to quote Seigel, but he's dogged by misfortune wherever he goes. He must be the unluckiest person ever to appear on the Forbes list of the top earners in the entertainment industry. He's a walking illustration of Sod's Law: whatever can go wrong, will go wrong.

This, I think, is why I identify so strongly with Larry David and his various creations: I seem to be cursed by the same malignant god. For instance, I've just written a new memoir about my struggle to be a responsible husband and father in which I describe an incident that occurred the day after my daughter was born. Like most new dads, I arrived at the hospital clutching a digital camera, hoping to take a picture of Caroline and the baby with a view to emailing it to all our friends. However, as I walked across the maternity ward I couldn't help noticing an adorable-looking black baby - and that immediately gave me an idea. Wouldn't it be funny, I suggested to Caroline, if I took a picture of her holding the black baby and emailed that picture to our friends instead. No explanation, just the words, "Marcellus was born yesterday at 9.52am. He weighs 10lbs 3oz and Caroline reckons he's going to be a boxer." Not surprisingly, my wife wasn't amused - and neither was my mother-in-law who was standing right behind me.

Of course, whenever something like this occurs, I'm not entirely cast down. A little voice at the back of my mind says, "This could make for quite a funny story" - and out comes my little black notebook. When I recently sat down with Robert Weide to discuss the film of How to Lose Friends, I was delighted to discover that Larry, too, has a little notebook that he always keeps in his breast pocket.

The term "comic genius" is bandied about so often these days that its currency has been almost completely devalued. Yet Larry David is the genuine article. He possesses the kind of comic brain that comes along once in a generation and I have no doubt that in 100 years time he'll be ranked alongside P G Wodehouse and Kingsley Amis as one of the best comic writers of the modern age. He's not simply a genre master; he's an artist. Wanting to be him isn't, in the end, some sad little fantasy - or, at least, it isn't just that. It's the highest tribute a fledgling comedy writer can pay to the greatest comic mind of our era.

Toby Young's latest memoir, 'The Sound of No Hands Clapping' (Abacus, £11.99) is out now