In the 1970s, Stuart Hample was a struggling cartoonist. Then he hit on the idea of turning the angst-ridden life of his favourite standup comedian, Woody Allen, into a comic strip

In the early 1960s, I saw Woody Allen perform, sometimes for no pay, at comedy clubs in Greenwich Village – the Bitter End, Upstairs at the Duplex – on occasion falling flat. There was the night he got no laughs. Working for no money, or maybe 50 bucks, and not a single laugh. None (except from me at the rear of the room). The material, of course, was singularly original, luminously funny.

Afterwards, in the dressing room, Woody was despondent. His manager, Jack Rollins, lit up a cigar and said: “What went wrong, Wood?” “The audience was hostile,” Woody said. Rollins exhaled thoughtfully. “An audience has to like you, to connect with you emotionally before they’ll laugh at your jokes. They sensed that you were fighting them.” He bit off a speck of cigar leaf and continued: “Could you come out and do your act, just for yourself, regardless of whether you get laughs or not?” Woody wasn’t sure. Jack urged him to try it for at least 20 performances.

Fast forward to 1975, a pretty good year. President Nixon was gone. The US pulled out of Vietnam. Charlie Chaplin was knighted. I sold a comic strip called Rich and Famous. But Rich and Famous failed to make me either of those things. I turned out the strip at night; by day, I ground out TV commercials for a cigarette brand furtively peddling cancer. My dream was to find another way of putting food on the table.

I had a lightbulb epiphany. It occurred to me that Woody might make a terrific comic strip. But how would he – 39 and by now wildly successful – react? I ran a test scene in my head. Me: ”Woody, I have an idea for a comic strip based on you. Possible?” Woody: “Sorry. Up to my neck writing a movie, editing another movie. Writing a piece for the New Yorker. Don’t need the money. Try me next year.”

So I asked him in person. Woody was intrigued enough to say: “Show me some sketches.” I based my drawings on how he looked in his late 20s, when we’d first met. He OK’d the Woody cartoon character (he even had it animated for a sequence in Annie Hall) and said: “What about the jokes?” I brought jokes. He looked through them. “Maybe,” he said, “I could help you with the jokes.”

Assuming he was offering to write them, I wanted to shout: “My saviour!” Instead, I said: “OK.” Which was more appropriate, since his help turned out to be dozens of pages of jokes from his standup years. Some were mere shards, such as “tied me to Jewish star – uncomfortable crucifixion”. Others were even more minimal: “bull fighting”, “astrology” (Woody occasionally translated these hieroglyphs).

Angst-ridden, flawed and fearful

But there were longer notations: “Sketch – man breaking up with female ape after his evolution.” And there were little playlets: “Freud could not order blintzes. He was ashamed to say the word. He’d go into an appetiser store and say, ‘Let me have some of those crepes with cheese in the middle.’ And the grocer would say, ‘Do you mean blintzes, Herr Professor?’ And Freud would turn all red and run out through the streets of Vienna, his cape flying. Furious, he founded psychoanalysis and made sure it wouldn’t work.”

A newspaper syndicate agreed to publish the feature. They requested six weeks of sample strips. I went each Saturday to Woody’s Fifth Avenue penthouse, where he judged the material and offered suggestions on how to develop characters and pace gags, and pleaded with me to maintain high standards. On 4 October 1976, the strip was launched. Woody, the pen-and-ink protagonist, was angst-ridden, flawed, fearful, insecure, inadequate, pessimistic, urban, single, lustful, rejected by women. He was cowed by mechanical objects, and a touch misanthropic. He was also at odds with his antagonistic parents; committed his existential panic to a journal; had regular sessions with his passive-aggressive psychotherapist; was threatened by large, often armed, men; and employed his modest size to communicate physical impotence the way Chaplin, in the guise of the Little Tramp, suffered humiliation.

I often wondered why Woody gave the concept a green light. In 1977, he related the following anecdote. He had cast the actress Mary Beth Hurt in his movie Interiors. Hurt regularly phoned her mother in Iowa to reassure her that she was safe and happy. During one of those calls, she proudly announced that she was going to play Diane Keaton’s sister in a movie “by somebody you probably haven’t heard of, a director named Woody Allen”. “I know about him,” said her mother, “he’s in the funny pages.” Woody’s manager figured it was no bad thing if his image was disseminated daily out in the heartland.

I took on a handful of writers. The star was David Weinberger, a brilliant 26-year-old PhD student in philosophy, who submitted some jokes out of the blue and won instant praise from Woody. Like all new strips, we lost a few newspapers along the way. The folks at the syndicate became nervous. I started receiving notes of caution: go easy on God references so we don’t offend Bible Belt readers; don’t do gags with Woody in nightclubs – they compare unfavourably with his live performances; change the name of your character Death to Fate. (Woody said: “Better to call him Death. A character named Death can be quite funny. You have to take some chances. It’ll be more alive if you use Death. Besides, you don’t want just another strip that succeeds, do you?”)

Woody always envisaged I’d give him a wisecracking, zeitgeisty cartoon that would deal with relationships, politics, social commentary. He wanted his strip to be amusing but also intelligent. But the anxious syndicate honchos demanded more gags and subjects accessible to the largest possible readership. Woody’s response was that an artist has to follow his own intuition, rather than obey some huckster driven by readership surveys.

This is borne out by my notes from a meeting with Woody, during which he said: “We will gain more than we will lose by establishing an identity; my tendency would be to risk being more offensive. I always believe that if I love a thing, 90% of the time there will be some people out there who also like it.”

Woody’s scribblings to me on the strips I sent for his approval offered suggestions: “The key is developing people. They must have desires – goals – so we are interested in them. I still feel you must be daring. The strip can probably exist on the level of ‘cute’ little jokes each day, but if you really want to involve the readers, it needs more substance – more plot.”

Another Woody reminder: “We need more strips I’m not in. My folks. My lovers.” And another: “We must not just use jokes that exploit my image – jokes should have genuine insights. Don’t pander. Don’t be afraid to be far out. Lead your audience; don’t look to them to lead you.”

And: “Need more character engagement – instead of jokes being free-floating, they must be jokes on the way to character development. Jokes are like the decorations on the Christmas tree – but it’s a beautiful tree you need to start with. Only then can you hang baubles on it. (Sorry for the disgusting metaphor.)

“Please don’t make me so masochistic. I’m not in life. Trying and failing is funny. Masochism is not.”

Meanwhile, the executives continued to fire off cautionary messages: aim at the broad base; the strip is too philosophical; let’s not have such an emphasis on therapy jokes. When the director of sales told me we had lost a paper in California because the editor felt the strip dealt too much with rejection, disappointment, and sometimes even God, Woody said: “I take that as a compliment. What’s the worst thing that can happen? So they’ll cancel the strip.”

Off to the therapist with Woody

Equilibrium returned periodically, courtesy of Woody’s steadfast sense of irony. One Saturday, he said: “I’m getting a ride to my therapist’s. If you want to come along, I’ll have my guy take you home.” We climbed into a waiting car. I noticed the ubiquitous floppy fedora he wore to conceal his identity, resting on the armrest. After a 10-minute drive, the car rolled down Fifth Avenue to a sleek apartment building and pulled to a stop. The sidewalk was empty. Woody sat unmoving, chatting amiably. But then, when a gaggle of pedestrians appeared, he jammed the protective hat on his head and dashed into the building.

A few days later, I drew this sequence in a strip. In the last drawing, Woody lies on the couch, having escaped the crowds, and complains to his therapist: “I’m so lonely. Nobody talks to me.” When Woody came upon it, he simply said: “Very perceptive.”

Working with Woody was smooth sailing: he was modest, efficient, dependable, focused, loyal, generous, incisive, serious, and witty. But quietly so. Even when an archetypal Allen quip slips out, there are no eye-rolls, no grandstanding, no bada-boom. He doesn’t hang out with comics, he doesn’t seek the limelight at awards shows, he doesn’t demand his name above the title. He also has incredibly clean hands.

Woody’s DNA is here and there in the strip, but he did not write it. If he had, it probably would have had a smaller audience – but it would have been a hell of a lot funnier.

This is an edited extract from Dread and Superficiality: Woody Allen as Comic Strip, published by Abrams on 2 November at £19.99. To order a copy for £18.99 (free UK p&p), go to guardian.co.uk/bookshop or call 0330 333 6846

The creator of The Thick of It and In the Loop reveals the movie moments that helped to build his own sense of humour – and still make him laugh

Some jokes never lose their appeal – they just get better with time. One of Britain’s leading comic talents is to reveal the debt that he owes to film history by naming the comic moments that have shaped his own sense of humour.

Armando Iannucci, the creator of The Thick of It and In the Loop, will name what he regards as the funniest moments in cinema when he speaks later this month at the annual Screenwriters’ Festival in Cheltenham. Top of his list are sequences from The Graduate, Woody Allen’s Play It Again, Sam and Ken Loach’s 1991 Riff Raff, which is set on a British building site.

“They are just scenes that made me laugh but, more than that, they are the ones that still stand out in the memory,” said Iannucci, who is currently editing the later episodes of a new series of the award-winning comedy The Thick of It, which begins its run on BBC2 on Saturday.

“Lots of things make me laugh, of course, but these are the bits I always want to see again, whether they are silly or clever,” he explained. “They are each very striking in different ways.”

Iannucci has also chosen the risqué banter between Barbara Stanwyck and Henry Fonda in 1941 screwball comedy The Lady Eve. Directed by Preston Sturges, who also wrote the screenplay, it is one of those offerings from Hollywood’s heyday that seems remarkably modern for its day:

Stanwyck: I hope you didn’t mind my asking you to breakfast.

Fonda: It wouldn’t be polite if I said I did, would it?

Stanwyck: No, I don’t suppose it would.

Fonda: And it wouldn’t be true either. You have the darnedest way of bumping a fellow down and bouncing him up again.

Stanwyck: And then bumping him down again.

Fonda: Oh. I could imagine life with you being a series of ups and downs, some irritation, but very much happiness.

Stanwyck: Why, Hopsie! Are you proposing to me so soon?

Fonda: No, of course not. I’m just…

Stanwyck: Then you ought to be more careful. People have been sued for much less.

Fonda: Not by girls like you.

The comic writer has also selected a scene from the closing frames of Buster Keaton’s 1928 classic, Steamboat Bill, Jr. It features a storm that wakes up a sleeping Keaton and then blows away a hospital. Iannucci is an admirer of Keaton’s perfectionism. “Scenes like this are just so cleverly done and worked out that they still don’t feel old at all,” he said.

“I don’t really have an overall theory about film comedy, or why these scenes appeal to me so much, but they have all been quite influential,” .

Iannucci has picked the scene from Loach’s Riff Raff that shows a family walking together through parkland after a funeral. “It is all shot in one take,” he recalled. “And they just start fighting over the ashes. It is very well done.”

The scene chosen from Mike Nichols’s 1967 film The Graduate shows the young hero Benjamin Braddock, played by Dustin Hoffman, being led into an adulterous liaison with Mrs Robinson, played by Anne Bancroft, in a hotel suite. “There is a lot of silly stuff about whether or not he has a toothbrush with him,” said Iannucci, “but the thing I really love about The Graduate is the fact that you just think of it as a film, rather than as a comedy, and then when you see it again you realise how very funny many of the scenes are.”

Honourable mentions will also go to films such as 1980 spoof disaster movie Airplane!; to This Is Spinal Tap, the fake rockumentary from 1984; and to romantic comedy What’s Up, Doc? from 1972, which stars Ryan O’Neal and Barbra Streisand. “I am a big fan of Bill Forsyth films such as Gregory’s Girl and Local Hero, so I will try to work in a mention for one of those in my list, too.”

Some of his plaudits are destined for Play It Again, Sam, Allen’s powerful early comedy. “I have chosen the scene where Woody takes a girl back to his place and is very, very nervous while putting on some jazz and then accidentally trashes the place. It is an amazing visual performance and yet it is all quite natural, somehow,” he said.

While there is little slapstick in the new series of The Thick of It, which features the arrival of actress Rebecca Front as the thrusting new minister of the department, there is the tight plotting necessary for screen farce to work well. “We do have a bit of running in the new series, but not much physical humour, although there is a touch of hotel-style farce in one later episode,” revealed Iannucci.

Screen comedy and its role in society will be one of the major themes at the Screenwriters’ Festival this year, with a debate on the future of political satire. Paul Bassett-Davies (Spitting Image) and actress Francesca Martinez will also chair a panel charged with deciding where the boundaries of good comedy may lie.

The Screenwriters’ Festival will run from 26 to 29 October at the Cheltenham Ladies’ College. For details, go to www.screenwritersfestival.com

The veteran film-maker has been offered $2m to shoot his next movie in Rio. Here are a few things city chiefs should do to ensure they get a Vicky Cristina Barcelona and not Scoop

Brazil might have the 2016 Olympics and a growing reputation as a potential economic superpower, but it knows that it can’t be seen as a truly developed nation until it gets one more thing – a neurotic, barely-watched movie made by an elderly man with an unhealthy Scarlett Johansson fixation.

Luckily, its wait seems to be over. Rio de Janeiro’s city chiefs have apparently offered Woody Allen $2m (£1.23m) of subsidies to persuade the director to film his next movie there. And on paper it seems like quite a good idea, especially for Woody Allen.

After all, when he went to Spain, Vicky Cristina Barcelona ended up winning him a Golden Globe. And his first venture in London, Match Point, was widely celebrated as a return to form – although following on from The Curse of the Jade Scorpion, you could argue that a YouTube video of a cat falling off a table would be seen as a return to form in comparison.

However, if the Brazilians are smart, they won’t offer the money to Allen without making a few very important stipulations. After all, is an extrovert nation such as Brazil really right for Woody Allen and his increasingly leaden neuroses? He only managed to capture Vicky Cristina Barcelona’s Spanish pizazz by channelling it through uptight Rebecca Hall and her “look at all these funny foreigners with their hilarious accents and crazy gestures” world view. That tactic might also work in Brazil, but do we really need another Woody Allen film about an anxious American observing a different culture’s wild over-emoting so soon?

Therefore, the Brazilians must tell him that he’s only allowed to make one film in Brazil before leaving. That way he can reflect the local flavour – albeit in a slightly preposterous cartoony way, as with Vicky Cristina Barcelona and Match Point – without repeating what he did in Britain and sticking around to destroy any goodwill he’d managed to build up with more movies that were either pointless (see Scoop) or the fruits of a bizarre “who can do the most woefully hamfisted regional accent” competition between Colin Farrell and Ewan McGregor (see Cassandra’s Dream. Or rather, don’t).

Plus, the Brazilians should stipulate that Allen himself must definitely star in the movie, preferably as a carnival dancer. But that’s only because the world sorely needs to see a 73-year-old Jewish man flapping around in the streets with his top off. That one should be a deal-breaker.

But once he’s agreed to these stipulations, Allen should definitely go and make his movie in Rio de Janeiro. If nothing else, it’ll strengthen his reputation as a director who’ll shoot anywhere if he’s offered enough money. And you know what that means. That’s right – if we all pool together and start saving now, then it won’t be long before Woody Allen will have to set one of his movies on the Isle of Sheppey.