Woody Allen’s Annie Hall (1977) is arguably his best film. It’s a witty time of it, with some fantastic writing and great performances from a talented cast.

Diane Keaton is central to it all as the goofy, loveable Annie. This role turned her into a style icon of the ’70s.

But Allen is ever-present in neurotic form, in a film that’s oddly timeless and reflective on humanity’s pursuit of hooking up with one another.

Love, Breakups, and ’70s New York in Annie Hall

The way Annie Hall plays out feels very autobiographical. Written by Allen and Marshall Birckman, the former was 40 when the film launched.

It’s set in New York, 1975, and Allen’s character in the film, the comedian Alvy Singer, references that on a few occasions. Particularly when he points out the “modernity” of 1975 but, by heck, this film is almost 50 years old now.

Annie Hall opens with Singer pondering on how his relationship with Hall (Keaton) ended 12 months ago.

We then get time lapses into Singer’s early life growing up in Brooklyn, where he was interested in girls by age six and bothered his mother by ruminating over the pointlessness of existence.

Precocious, then, and intellectually advanced.

The film then cuts back to how Hall and Singer met (during a tennis game set up by friends). Annie is smart, has great dress sense, is cool and beautiful. She’s also awkward and goofy.

Seriously, though, that dress sense. This was filmed in May 1976—cut to now and any woman could go out dressed like that and look amazeballs.

Apparently, these were just Keaton’s clothes she wore all the time. Kudos to her!

After the two meet is when Allen starts to mess around with the romantic comedy tropes. Just making everything a bit more inventive.

He begins to throw in some innovative ideas, adding clever little tricks into the film. Such as these “honest subtitles” as the two discuss culture.

The two hit it off as they share the same sense of human and enjoy giggles and whatnot. Hall is free-spirited and relaxed, as a passion singing in local New York clubs hoping to get a singing career going.

Singer is neurotic and overly-intellectualised, obsessed with death and even buying her books about the subject as a, kind of, bizarre way of explaining his love for her.

Allen’s hyper-active brain crams so many little gems into the script.

For example, there’s a brief scene with Hall’s brother Duane (played by a young Christopher Walken) where he makes an unusual confession to Singer.

Eventually, Hall cools towards Singer and a gradual breakup begins. Singer is left to ruminate over this and what went wrong, as the two remain friends.

Singer begins seeing other women, whilst Hall seems to have a flirtation going on with Paul Simon. As in, the Paul Simon (played by Paul Simon of Graceland album fame and many other hits) one of several cameos from famous people across Annie Hall.

The odd thing we found about the film was the series of women Singer dates. The insinuation is it’s his brains and wit that are getting him a continuous line of beautiful younger women interested in him, but we just didn’t find that believable.

Starting off with Diane Keaton, then there’s Shelley Duvall (who later starred in 1980’s The Shining). Plus there’s Beverly D’Angelo, Janet Margolin, Carol Kane, and Sigourney Weaver.

We can only view this as an ego exercise for Allen, as we can’t see a very striking, tall, statuesque individual like Weaver dating him. Amongst the very many offers someone like her would get.

No offense, Mr. Allen, just maybe a reality check on that one.

Anyway, to comprehend the end of the relationship Singer stages a play of their relationship in New York. And he’s left to conclude that love is essential, even if it is neurotic.

The film ends to the tune of Hall singing Seems Like Old Times.

Which wraps up what’s possibly Allen’s best film. It stands the test of time very well, feeling extremely modern in its take on relationships.

Despite the proliferation of dating apps these days, the dating world is still largely as fickle, shallow, tumultuous, and weird as it was 50  years ago… from what we can tell, anyway, but this film seems to more or less confirm it.

Lots of dating, sleeping around, and pontificating over why it’s so difficult to find your ideal match (and when you do, wondering why it then falls apart).

There’s an excellent cast here. Diane Keaton was brilliant as the loveable Annie, bagging herself a Best Actress Oscar for her efforts.

Allen and Marshall Brickman’s script is still super sharp, offering a witty examination on the confusing dating landscape and an eternal pursuit of love.

It’s an entertaining and charming watch, now with the added bonus of being something of a time capsule representing New Yorker life from the mid-’70s.

Annie Hall as a Showcase of Emerging Talent

One of the intriguing aspects of Annie Hall was the inclusion of talented young actors (pre-fame) who went on to much bigger careers.

Many of them only had minute screentime. Such as a young Jeff Goldblum above in his screen debut—looking very handsome, we must add.

As we’ve also mentioned there were young actresses there too, including Shelley Duvall, Beverly D’Angelo, and a brief appearance of Sigourney Weaver in her screen debut (although you can barely tell it’s her as it’s a long distance shot).

Christopher Walken’s brief role was also a pre-fame one. He starred in The Deer Hunter in 1978, which helped to make his name.

There are some notable cameos, too, especially from writer Truman Capote. Paul Simon also had a slightly more extended role, inviting Hall and Singer to a party of his outside of New York.

There was also a brief role for Laurie Bird. Sadly, she committed suicide in June 1979 at the age of 25 (her mother had also done so at the same age). She was in a relationship with Art Garfunkel at the time, who indicated she “wasn’t happy with herself”.

The Production of Annie Hall

The film was a commercial and critical success. From its $4 million budget it recouped some $44 million. It also won four Oscars, including Best Director for Woody Allen and Best Original Screenplay.

Allen picked Gordon Willis to be his cinematographer, unusual as he’d worked on the likes of The Godfather (1972). Not breezy comedies such as this one.

But Willis’ involvement added a more professional look to the film over Allen’s previous productions.

Allen also added some fourth-wall breaking moments, sometimes talking to the audience directly and breaking up scenes with social commentary. He also added in a Disney-styled animation based on Snow White.

As he put it in the book Woody Allen on Woody Allen (1993):

“Because I felt many of the people in the audience had the same feelings and the same problems. I wanted to talk to them directly and confront them.”

But he wrote the role of Annie Hall specifically for Diane Keaton. She’d worked with him before on Play It Again, Sam (1972), Sleeper (1973), and Love and Death (1975). She remarked the Hall role was a dreamy version of herself, packed with a desire to be a singer, but suffering from insecurities.

The shoot began on May 19th 1976 in Long Island of New York.

There was a very loose schedule to follow with a lot of ad libbing, leading to the first edit of the film not being satisfactory. For the second cut, the film turned to a more linear narrative and that’s where the classic Annie Hall emerged.