Woody Allen

Woody Allen is a tough director (and writer and actor) to recommend. He can be really off-putting, and in fact the first time I saw a movie he starred in I refused to watch any more for a long time. He’s an insane combination of whiny and cocky, although once you figure out which parts of that are self-deprecating it helps (or else stick with the ones he doesn’t star in). Plus he has one of those personal lives that completely distracts from everything he’s ever done. I’m not going to get into that beyond the fact that he probably does personally suck and I don’t think I’m funding his past crimes if he gets one cent from me watching his decades-old movie on Netflix.

So why is Woody Allen worth the hassle? The guy just knows what’s interesting and shows it in observational comedy, smart conversations, big thrills, and a shooting style that draws you in to all of those.

I’ve mostly worked my way down the list of the ones generally thought to be the best, and stopped once I figured I didn’t need to seek out 30 more of this quality or less. Seriously, the guy just cranks out movies. The last year he didn’t release a movie was 1981. So if you watch and enjoy all these and want more I can say Scoop, Melinda and Melinda, Celebrity, and Zelig are all varying degrees of pretty good. If you’ve seen anything released after Midnight in Paris let me know if it’s good!

Annie Hall

A neurotic stand-up comic (Allen) thinks back on his relationship with a quirky aspiring lounge singer played by Diane Keaton. He recounts their fun times, fights, and the events of his life that caused him to want to date her.

This is Woody Allen’s most acclaimed movie. Here he shares emotions and fears most of us keep to ourselves, bouncing back and forth between self-hate and self-importance. He’s always willing to take a break from sharing his realistically messy relationship with Annie to take down snobby New Yorkers or show embarrassing stories from his youth.

But basically the guy is a bit much. His faults don’t compensate enough for his qualities in his relationship with Annie and they don’t really for me either. I appreciate Annie Hall’s importance but I think he’s done better and I’d say check out some others first to see if you can tolerate this character of which he frequently plays some variation.

Annie Hall is frequently lumped in with Manhattan, which came out two years later and which I prefer.


A writer who has just quit his hack TV job has to choose between his teenage girlfriend and his friend’s mistress. He tries to make it as a writer but needs to afford alimonies for his two ex-wives, one of whom is releasing an embarrassingly detailed book about their relationship.

Somehow Allen makes his character more likable through objective crappiness and I don’t understand why it works that way. Maybe since he can’t be serious his bragging comes across less like an entitled rom-com lead and more like a scoundrel trying to convince himself.

To me Manhattan surpasses Annie Hall through simply adding many varied and interesting characters. This broadens the focus beyond one man, showing society’s bizarre complexities and giving a context for its humorous dialog. Plus it’s just a bizarre situation and I wanted to see how its twists would turn. Manhattan looks fantastic. Never in the hundreds of movies shot in New York have I enjoyed just checking the place out this much.

Broadway Danny Rose

Allen plays Danny Rose, a tireless talent manager to an amazingly talentless clientele. When his wash-up singer gets a chance at a big comeback, he wants both his wife and mistress Tina to attend his concert. Danny must pretend Tina (Mia Farrow) is his own girlfriend, which gets tough when a mobster turns out to be interested in her too.

A fully likable lead – what a novel concept! Danny Rose genuinely treats his clients like his friends and makes any sacrifice to help them succeed in their inevitably doomed show business dreams. We want to see what events the plot unfolds but even more we need to see if Danny’s kind enthusiasm can withstand them. This is easily the most heart-felt I’ve seen of Woody Allen and I strongly approve.

Hannah and Her Sisters

Sisters Hannah, Lee, and Holly have just a mess of a family dynamic. Hannah (Mia Farrow) tries to set up unsuccessful Holly with her hypochondriac ex-husband, while her current husband (Michael Caine) pursues recently-single Lee.

I watched Hannah and Her Sisters because it won Best Original Screenplay at the Academy Awards and boy do they get it right sometimes. Woody’s more focused schtick works well as comic relief to some very real relationships and conversations. I doubt many sisters interact like this but it would be a lot more interesting if they did. Allen did a great job directing the excellent cast towards the exact characteristics that made the potentially convoluted relationship web fit together.

Crimes and Misdemeanors

Respected ophthalmologist Judah Rosenthal’s mistress threatens to tell his wife about their affair. He asks his dangerous brother for help. Meanwhile documentary filmmaker Clifford Stern must make a movie about his cocky TV producer brother-in-law to get ahead in the industry.

In Crimes and Misdemeanors Allen’s comedy adds to a dramatic story more cohesively than anywhere else. Both parts allude to similar questions about reputation and ruthlessness and choice. It’s also where Allen’s skill at directing conversations hits hardest, moving between imposing and comedic.

This ends what’s considered his earlier period of quality. We move forward over 15 years (and supposedly a lot of mediocre movies) to his more modern stuff.

Match Point

Former tennis star Chris Wilton works his way into Tom Hewett’s wealthy family when Chloe falls in love with him. He risks losing it all by pursuing Tom’s American actress girlfriend Nola.

Here Woody removes NYC, his typical dialog style, his frequented intersecting storylines, and himself as an actor and what’s left is pure excellence. His skill at shooting conversations pops when he replaces some of the wordiness with innuendo and knowing glances. Comedic timing makes way for that of movement and drama, which excites and horrifies. This movie alone makes Woody Allen certified great. Watch Match Point. Watch Match Point. Watch Match Point. Watch Match Point.

Vicky Christina Barcelona

Two American tourists are seduced by a free-spirited Spanish artist. Things start to fall apart when his fiery ex-wife comes back into his life.

I hate this movie! Every character is like an awful stereotypes horny teenagers would think up. The whole plot is either pathetic wish fulfillment or an attempt to prove how comfortable one can be with a spouse’s former promiscuity. After decades of stories about relationships and cheating Vicky Christina Barcelona forces us to ask if Woody Allen learned anything past 1960s sexual liberation. I’ve seen a few people claim this is a parody of all its cliches, I think because the actors are super all-in on the ridiculousness, but if that’s no point. Selfish, mercurial relationships are exhausting? SHOCKER. Only watch Vicky Christina Barcelona if you want to see how much you can hate the phrase “make love”.

Midnight in Paris

A struggling writer visits Paris with his fiancee’s family. They study museums with her snobbish ex-boyfriend but he prefers to indulge his deep 1920s nostalgia on long night walks. He finds the ultimate inspiration when he witnesses some of Paris’s magic.

Allen replaces his usual cynicism and amorality with Owen Wilson. Classic take-downs of pseudo-intellectuals automatically become unassuming and fun. He’s easy to root for wholeheartedly. There’s a whole gang of great actors in great roles. It feels like cheating for a deep look at important subjects like art and dreams and dissatisfaction to be this pleasant. Even if you dislike other Woody Allen films you’ve seen you should still watch Midnight in Paris.

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