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John Cleese, the co-founder of Monty Python’s Flying Circus, is one of the greatest and most prolific comic writers and actors in history. Since escaping England’s ultra-middle-class Weston-super-Mare and joining the Footlights drama club at Cambridge, where he studied science and then switched to law, Cleese has produced a steady stream of sketches, one-man shows, TV appearances, movie roles, voice-overs for animated and video-game characters, commercials, training videos and TV specials. (His $20-million divorce from California psychotherapist Alice Faye Eichelberger in 2008 has forced him, by his own admission, to earn an additional $1-million a year until he turns 76 next year.)

The most recent addition to Cleese’s ever-expanding oeuvre is his new memoir, So Anyway …, a funny, briskly readable account of his life and the evolution of his sense of humour, from childhood to the early days of the Pythons. In addition to redefining comedy and television in the 1960s, Cleese created the legendary sitcom Fawlty Towers (with his first wife, Connie Booth), appeared in four Monty Python movies, and wrote and starred in A Fish Called Wanda, which was nominated for an Oscar for best screenplay.

The master comedian has even voiced a set of directions for TomTom, the GPS in-car directional device – which happened to be the starting point for Cleese’s on-stage conversation in Toronto earlier this month with Globe and Mail feature writer Ian Brown. An excerpt:

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Cleese: I have to tell you something funny [about the TomTom voice over]. My daughter downloaded it, started using it. She said it was impossible for her to actually do what I say.

Brown: There was a story in the newspaper a year ago about an elderly English couple following the instructions of a GPS device who drove through the wall of an ancient church. I hope that had nothing to do with you.

Cleese: No. In the old days, we used to do things like look through the windscreen and see where we were going. And then there was this wheel in the middle and if you turned clockwise, the car went to the right? It’s too much for people now.

Brown: Should we talk about the book at all?

Cleese: Which book? Yes, we’ll talk about the book.… But the only thing that matters is we don’t [care about it]. [Loud, sustained applause.] The one thing you learn in my business is, if something goes wrong and you’re embarrassed, the audience tightens up, and they feel awful for you and they feel awful for themselves. But if you don’t care, if you’re not thrown by it, you can get away with anything.

Brown: In your book, you do say timing is your only talent. That you’re not creative.

Cleese: Well I’m sort of creative, but I have no musical talent. When I was in a Broadway musical I was forbidden to sing. I dance like an Englishman. People say, “Oh, you’re so multitalented.” No. I can write some funny stuff and I can act it sometimes, and I’m a jolly good chairman.

Brown: What are the salient characteristics of a good chairman?

Cleese: A good chairman gets everybody to speak, and he doesn’t make his mind up in advance. Because the essence of creativity is divergence of opinion.

Brown: Your father was a kind man. But your mother sounds like she was a paranoid lunatic.

Cleese: I think that’s understated. For example, if she couldn’t get her own way, then she would have a tantrum. It’s like a lot of the women that I’ve dated. They rule through weakness. You say: “Well I don’t mind so much.” And they say: “Well if we don’t have the Rolls-Royce, I won’t be able to bear it.” [Laughter] So you say: “All right, let’s get a Rolls-Royce.”

Brown: Did that difference make you creative?

Cleese: In my case, we moved a lot, and my parents disagreed. If your parents are constantly arguing, then you have two different points of view and you’re trying to figure out how they could fit together or where they don’t fit; and this business of trying to reconcile two frameworks seems to make people creative. I’ve always called myself “John Cleeze.” Because in 1893, my Dad was born Reginald Francis Cheese. And he changed the “H” to an “L” when he went into the army in the First World War. He’d been teased too much. But my mother called it “Cleese.” I always felt if your parents couldn’t agree on the pronunciation [of their last name], they were not likely to agree on a lot else.

Brown: In your book you claim you were a virgin until age 25, which was surprising. You seem to be a very charming fellow.

Cleese: I am! But if your first contact with the female species is with a woman like my mother, you don’t immediately feel tremendously at ease with them. And if you then spend 10 years in the British private-school system, where everyone is a fellow. … Then I met a very nice girl in New Zealand, who just decided it was going to happen, and she followed me to Auckland. And in the Auckland hotel, in about August of 1965, I lost my virginity.

Brown: They’ll probably put a plaque in that hotel room now.

Cleese: They should! They should. It would be very good, wouldn’t it? They always say “He built the Tower of London.” But if you had “The Duke of Marlborough lost his virginity here …”

Brown: I’d take the tour.

Cleese: I love those plaques. You could make your own, couldn’t you? You could invent people. And claim stupid things about them. And put them on your house!

Brown: In any event, you’re on your fourth marriage.

Cleese: To an English girl. I married three Americans, and I thought, well, you know, that’s the lesson there. I better try something else, and I met this extraordinarily beautiful woman [jewellery designer Jennifer Wade, who was 38 at the time]. It’s quite nice to know that at the age of 69 you could meet the love of your life. Particularly when you’ve had as many expensive disappointments as I have. You see, I never made the sort of money that Americans made. I mean, for a season of Monty Python, I used to earn £4,000. The money for working for the BBC was like being a successful bank manager.

Brown: No way.

Cleese: No, seriously. And when Monty Python got shown in New York City, I used to get one quarter of 1 per cent of the original performance fee, which was £240. It was enough for a nice starter in a restaurant. And that’s for an entire series. So I never had huge quantities of money. I had this mansion in Holland Park with no mortgage. Now Jenny and I live in this rather small flat off Sloan Square with a mortgage, which is definitely going backwards. I was just doing stuff, doing lots of one-man shows, to earn the money to pay the alimony, whereas I would like to have been doing things that were more interesting and more creative. I have the skills of an actor, but I don’t have an actor’s temperament. I don’t really enjoy getting up and saying what I said the previous night. I want to write something, and then do it a few times till I figure out what works and what doesn’t work, and how I make it work, and then I want to move on.

Brown: One of your teachers in public school wrote in the back of your report card, “Cleese continues to act subversively in the back of the classroom.” You’ve been questioning things since the beginning.

Cleese: Well I think that’s because I went to an English public school. These were basically the schools that the middle class went to. People who went to grammar schools always said how confident people who had been to schools like mine were. We learned, just by copying each other, how to be middle-class, talking about things. But the thing that turned me on all the time was laughing. And I think maybe it was because it was a way of reminding me how ridiculous it all was.

I’m a phony professor at Cornell. And I’ve got a friend there who’s a social psychologist called David Dunning. David Dunning has always been fascinated to know whether people were able to tell if they were good at things or not. “Self-assessment,” he calls it. And he has discovered that in order to know how good you are at something requires almost exactly the same abilities as it does to be good at it. Which leads to a wonderful corollary, which is that if you’re absolutely no good at something, then you lack exactly the attitudes and skills that you need to know that you’re absolutely useless.

Brown: It certainly explains politics.

Cleese: It explains Hollywood. The world is littered with people who think they know what they’re talking about. And they have absolutely no idea that they don’t know what they’re talking about, and once you’ve absorbed this, it all becomes very clear, and in a sense it has the effect of relaxing one.

Brown: You say your aim, always, is to be “really funny.” Not “pretty funny,” not “witty,” not “charming.” How did you know, when you were writing, that you were being really funny?

Cleese: It was a nightmare. But my huge stroke of luck was to meet [Monty Python member] Graham Chapman at Cambridge. What I discovered was if Graham laughed while we were writing something, it meant that the audience was going to laugh. And he was solid gold to me for that.

Brown: He deplored “good taste.”

Cleese: The first time I saw it, I went to a party, and after about half an hour, I thought, “I wonder where Graham is?” Because I couldn’t see him around. And then I saw people going [mimics someone being startled], “Ugh!” And there he was, crawling along, biting people’s ankles. We got invited once to the Oxford Union, one of the snottiest, stuffiest, most stuck-up places you could find. He was invited, of all things, to talk about nuclear disarmament with a couple of politicians and well-known political pundits. He was dressed as a carrot. Everyone was supposed to speak for 12 minutes, and when he stood up, he had this little sort of green sprig on his head, and he just got up and he stood there. And he never said anything. Then he sat down again. And he had completely ruined the debate, and amused himself.

Brown: You were very surprised when he revealed he was gay.

Cleese: It didn’t happen much in 1966. It was much more dramatic when somebody came out. And when I met Graham, he used to wear these great, heavy broad shoes, and corduroy trousers, you know, and a rather hairy sports jacket with leather patches, and he smoked a pipe, and mountaineered, and drank a lot of beer, and was a medical student. In those days, those were not immediate signs that someone was gay. [Laughter] Unless of course it was a woman. [Laughter]

Brown: Did his alcoholism wreck your partnership?

Cleese: It was not until the end of the second series [of Monty Python] that we realized how serious the problem was. I can tell you exactly the day. We were shooting a film called And Now for Something Completely Different. It was a rather cold morning and we had this little trailer where we were all sitting, keeping warm. And we were trying to figure out what we were going to do in the next shot. And we needed a script, and we couldn’t find a script, and Michael Palin said, “Oh, Graham’s got a script in his little briefcase.” And we opened the briefcase up and took the script out, and then Michael almost went pale. And I said, “What?” And he pointed, and lifted out a bottle of vodka. And he said, “That was full when Graham came, got in the car this morning.” It was about half past 10 in the morning, and the bottle was half empty. And that was an awful moment when we all kind of went, “Oh.” And then it got harder and harder because we didn’t do Python for a year and during that time he went rapidly downhill, and got to the point where he couldn’t remember his lines. You’d spend all week polishing a piece of dialogue, and then he wouldn’t be able to remember it right. It was one of the reasons I wanted to move on.

Brown: Did you all compete with one another? Because you make some … remarks about how short Terry Jones is.

Cleese: But that’s undeniable. [Laughter] I mean I’m perfectly prepared, if you think it would make me a nicer person, to say that he’s very tall. He certainly lacks height.

Brown: And you imply that Terry Gilliam lacks any … any sense of intellectual logic.

Cleese: Yes, he is a very sad, confused creature. With a wonderful talent for producing extraordinary images. And no other talent at all. But Terry actually is so competitive that he gives competitiveness a bad name. I very nearly did Don Quixote once. And I was very sorry I didn’t, it was with an Australian director called Fred Schepisi, and Robin Williams was going to play Sancho Panza, I think it could’ve been rather marvelous. But they couldn’t raise the money. And when we got together to do the Python 30th, I’d heard that Terry had got the money to make The Death of Don Quixote, which is his take on it. And the first thing he said when he saw me was, “I’m making Don Quixote, and you’re not.” Now, there’s a certain competitive edge in that.

Brown: You considered alternative titles to Monty Python’s Flying Circus. Such as “A Horse, a Spoon and a Bucket.”

Cleese: Basin. “A Horse, a Spoon and a Basin.”

Brown: Oh, that changes everything.

Cleese: Michael Palin suggested that. I think it was a much better title.

Brown: “Owl Stretching Time?”

Cleese: That was Graham’s idea.

Brown: One of my all-time favourite pieces of your writing is the Cathcart Towers scene in A Fish Called Wanda, where Michael Palin can’t tell you what you need to know because he has a stutter.

Cleese: The reason I wrote that was because Michael Palin’s dad had a terrible stutter. And that is why he did it so superbly, because he’d been watching it all his life. People afterward complained, “How could you make fun of a stutterer?” It’s a very difficult question to answer, and I’ll tell you why. Because all humour is in some way critical. Because if someone behaves completely appropriately, if they’re flexible and they respond emotionally, and they do things that are appropriate to the situation, they’re not funny. Comedies are about things going wrong.

Brown: Why do you think people took to the Pythons so strongly?

Cleese: You always feel affection for people who make you laugh, even if it’s just a good friend who makes you laugh. But it’s more than that. Somebody once said to me that what they loved about Monty Python was that, after they’d finished watching it, they could not watch the news any more. It’s pointing out that nobody knows what they’re doing. There was a psychologist at the University of Philadelphia interested in whether people could make forecasts. And he got hold of lots and lots of the people who made their living out of being pundits, you know? And he asked them for forecasts of what would be happening within five years and 10 years. And he waited 10 years, and then he checked the forecast, and then discovered that they were absolutely hopeless. They were hardly better than chance. And the worst people were the most famous ones. And this is because of the affirmative bias. If you have a belief, and then you’re given a couple of bits of information, one of which reinforces your belief and one of which contradicts it, you’re much more likely to pay attention to the bit of information that says, “Yes, you were always right.” But they’re not really right. It’s all much more complicated than that.

This interview has been condensed and edited.