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Take the Money and Run (1969)
Having won fame as a stand-up comic, Allen had transitioned into films as a writer and actor with What's New, Pussycat?, What's Up, Tiger Lily?, and 1967's Casino Royale. Still honing his comedic style, he made a promising solo directorial debut with this madcap mockumentary about a would-be criminal.
I felt I was ready to direct, but the people in my corner said, ''People will resent it. They'll think, Who is this guy?'' So I tried to get Jerry Lewis...but we couldn't work it out with the studio. Then this new company, Palomar Pictures, formed, and they were willing to take a chance on me. The picture was very well received critically, but two or three years after it came out, they had still not broken even. I always had a tough time getting an audience. They'd book me into Caesars Palace in Las Vegas and they'd have half a house. By the third night, the head waiters would be pulling the potted plants in so they could make the space much smaller for the audience.
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A nonstop Orgasmatron of inspired silliness, this futuristic Rip Van Winkle comedy displayed Allen's growing storytelling skill, though the difficulties of creating the world of 2173 (giant bananas and all) forced him to pour his salary into reshoots. Most important, the film showcased his comedic chemistry with a young actress named Diane Keaton.
Marshall Brickman and I wanted to write a movie that wasn't just gag-gag-gag. I was good at writing gags, but to write a story with a real plot and real characters ? that was much harder. I had a small budget, and I was working in the future, so every car had to be built, every costume had to be designed. Fortunately, my costume designer was Joel Schumacher. He had, like, a $10,000 budget to do all the costumes, but he was brilliant and inventive.
I knew Diane very well. I had done a play with her, Play It Again, Sam, we had lived together, and we were very close. I just felt she had a limitless comic talent. I've always felt that the two great movie comediennes of all time were Judy Holliday and Diane Keaton.
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Annie Hall (1977)
In its initial two-hour-and-30-minute rough cut, Allen's artistic breakthrough was a formless collection of comic bits and pieces. After extensive editing, the 93-minute film that emerged would become one of the most iconic romantic comedies in Hollywood history and earned four Academy Awards, including Best Picture. Allen was a no-show at the Oscars.
The movie was originally supposed to be what my character was thinking, in a not really coherent fashion. But when Marshall Brickman saw the first cut, he said, ''I wrote it with you, and even I can't follow it.'' So we restructured it and reshot the ending many times. I was able to find the love story, and audiences were charmed by it beyond my expectations.
They gave the Oscars out Monday evenings in those days. I always played clarinet with my jazz band on Monday evenings. I don't like to fly. I don't like to get into a tuxedo. So I'm not going to suddenly cancel my band and fly to California. People made a big deal out of that, but I don't write movies to win awards.
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Allen's abrupt turn toward drama with this somber, Bergman-esque portrait of a family falling apart brought him his first major critical drubbing.
I didn't see it coming. There were people who loved it, and there were other people who thought I was committing a crime: I was in bad faith, I had violated my contract with the audience. I didn't feel it was fair. I thought I should be able to try something, even if I made the worst film in the world. After Interiors I knew there would be consequences if I tried to make that kind of film again. But I did it. Because the alternative is letting other people tell you exactly what to do in your career. Maybe they're even right, but, you know, it's hard to live that way.
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A wistfully romantic ode to Allen's hometown and an indelible portrait of angsty urbanites in search of love, this gorgeously shot, Gershwin-drenched comic drama grossed nearly $40 million, Allen's biggest hit up to this point, and was hailed as another triumph — by everyone but Allen himself.
I was so disappointed when I saw my final cut, I thought, If this is as good as I can do at this point, I shouldn't be making films. I went to United Artists and said, ''Look, don't put this out. I'll make another film, no charge.'' They thought I was nuts. And it was a very, very big hit. Audiences don't have the same criteria I do. They say, Okay, you had some grandiose idea and maybe you failed, but we like this film. So once again, I shut up and just felt I got away with it. I got off with my life.
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Stardust Memories (1980)
The most polarizing film of Allen's career concerns a successful director, played by Allen, whose midlife crisis plays out across a surreal, Fellini-esque canvas. Many were angered by the film's bitter, mocking portrayal of critics and moviegoers as sycophants and vulgarians.
I certainly did not think my audience was stupid or grotesque, the way they seemed to be portrayed in the movie. I never had those thoughts — and if I did, I was much too smart to express them. I had an idea about an artist who had everything in the world and still couldn't beat his sense of mortality. But it was taken as an act of hostility. I've played the part of the neurotic so intensely and so often, when a movie like Stardust Memories comes out, it's very hard for audiences to separate [me from the character]. A few months after the movie came out, John Lennon was murdered. In my movie, I show that exactly: The relationship between the audience and the entertainer is very often a kind of worship but also homicidal. I felt I had a good insight into that world.
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Hannah and Her Sisters (1986)
This novelistic look at the tangled lives and loves of three Manhattan sisters earned over $40 million, topping Manhattan as Allen's biggest-grossing film. But in his mind, it didn't come out the way he had intended.
I had written a different ending that was not as upbeat: Michael Caine's character is still hopelessly in love with [his wife] Hannah's sister, who has married another guy because he couldn't bring himself to act, and he's stuck with Hannah and it's going to be a nothing marriage. And I shot that ending. But when I looked at it, it was like the picture dropped off the table. It was negative — and not like a good, Chekhovian negative, it was an inept negative, a downer. So I guided the thing instinctively to an ending where all the characters came out happy, and the picture was very successful. But I never felt positive about it. I felt I had a very poignant idea but finally couldn't bring it home.
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Crimes and Misdemeanors (1989)
One of Allen's most deft balancing acts of comedy and drama juxtaposes a morality play about a prominent ophthalmologist (Martin Landau) who plots to murder his mistress, with a comic story featuring Allen as a struggling filmmaker.
For me, the interesting story was Marty Landau's story, and as I was putting that picture together, I so regretted that I had my story in there. As soon as I put myself in the picture, I felt that it ratcheted down in substance instantly, because I can only play a clown, a joker. I'm always seduced by serious stuff. I wish my gift in life had been Tennessee Williams' gift or Ingmar Bergman's or Eugene O'Neill's. It wasn't — my strong point was comedy. Comedy can never go as deep, by its very nature; when a situation becomes tense, you make a joke and it relieves it. These are just personal feelings of mine. Other people don't feel that way.
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Husbands and Wives (1992)
Allen's most caustic look at relationships in crisis hit theaters as his personal troubles were exploding in the press, bringing his decade-plus-long on-screen and off-screen partnership with Farrow to a crashing end.
The movie had no relation to my life in any way. But when it came out, my private life was all over the headlines. I could always work under stress, though. Whenever things go bad, the two things I've always been able to do are lose myself in work and lose myself in sleep. Work has always been a lifesaver. I can immerse myself in the problems of the second-act finale and avoid having to face the problems that are really unpleasant and that I can't deal with.
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Sweet and Lowdown (1999)
Sean Penn and Samantha Morton earned Oscar nominations for this bittersweet period piece about a callously self-absorbed jazz guitarist who is as reprehensible in his life as he is brilliant in his art.
I liked that movie — it was one of the ones, like The Purple Rose of Cairo  or Husbands and Wives, that came out very much the way I wanted it to. I had that idea almost from the start of my career, around the time of Bananas , and I was going to play the guitar player. I went to United Artists and they said, ''We assumed you were going to do comedies when we signed this contract.'' So I took it back and two weeks later I gave them Bananas. Years later, I rewrote it for Sean. When I was younger, I could have played it, but I never would have brought to it Sean's acting skill and his tortured persona.
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Match Point (2005)
Critics hailed Allen's Match Point as a comeback, but in his mind, he never went anywhere.
I had the idea for a while to do a murder story where the murderer kills the victim's next-door neighbor so it looks like the other murder was just in passing, to deflect the police. Then when I made the guy a tennis player, the metaphor came of getting the bounce one way or the other, and the thing evolved from there. People impute to it calculation and going in a different direction and ''this is what's happening in his private life so he does this or that.'' None of that ever enters into it remotely. I just sit in a room or walk the streets in New York and think, Gee, what should I do next? It's always just by sheer chance. I could make 10 movies in a row that would be as serious as Interiors or as light as Small Time Crooks . There's no way of me knowing. I'm just happy to get any ideas.
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Vicky Cristina Barcelona (2008)
Javier Bardem plays a well-known Spanish painter who romantically juggles two American college students: recently engaged Vicky (Rebecca Hall) and her wild-child best friend, Cristina (Scarlett Johansson). But when his emotionally unstable ex-wife (Penélope Cruz) enters the picture, a frisky love triangle grows complicated. This is Allen's third film with Johansson.
She's a wonderful natural actress. The trick is to play into her strengths. In this picture, it's something that I felt that she could play beautifully at this stage of her career. She's very young. When she did Match Point, she was only 19. She astonished me. And I did Scoop with her because I felt that she was a funny girl and she didn't have to play just a pretty sexpot. She could put glasses on and play a silly little college girl. And in this picture, she's one of my typical kinds of women: a very neurotic American young woman who is finding herself amid a sea of neurosis in a summer in Barcelona. And it just rolls off her very naturally.