How I turned Woody Allen into a comic strip

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
Woody Allen
Heard the one about Freud and the blintzes? … Woody Allen doing standup in 1966. Photograph: Bill Ray/Time & Life/Getty

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

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