Until it isn't.
Granted, he's had a couple of good ones recently - Vicky Christina Barcelona and Midnight In Paris were both good, but second-tier when placed up against the classics.
So imagine my surprise when, as Blue Jasmine unfolded, I suddenly realised that he'd actually done it.
Because, what makes a great Woody Allen film is, well, everything. There's not a spare piece of meat on these bones, no flab, nothing.
It's got laughs, it's got heartbreaking beauty, it's even got a wonderful twist which makes you doubt how you've been feeling. It's nothing short of beautiful.
Because what Allen does best - and few people can match him when he's on his game - is tell a story, with well-rounded characters you can relate to. A story that makes you think while you enjoy and engage with it.
He has a way of writing that allows the characters to breathe and develop and explain themselves without having to add unnecessary dialogue to drive the plot or character development, which has the benefit of never slowing things down.
The story centres around Cate Blanchett's stunning portrayal of Jasmine, a woman whose mental state has come crashing down around her along with her life.
Once rich and the centre of the New York social scene, she's now without a husband, a house or her step-son. Instead, she's been forced to shack up with her adopted sister Ginger (played exquisitely by the wonderful Sally Hawkins) in San Francisco.
And worse, she has to get a job.
By flicking between the past and the present, we are shown how events unfolded, how Jasmine has fallen on such hard times and is now having to answer a dentist's phone while also picking Ginger's life to pieces.
Blanchett captures the mental fragility and selfish beauty perfectly. You ought to despise her, but you can't. Through her portrayal you sympathise and care about what has happened to Jasmine, and when she meets her next Mr Right, you are genuinely pleased for her.
Even if she is a pill-popping alcoholic who is falling apart at the seams, you still care what happens to her. To the extent you actually find yourself siding with her when she's being a snobbish cow to Ginger's boyfriend.
But this isn't simply a two-woman show (although, if it were, what a show that would be), oh no. The rest of the cast put in stellar performances too.
Alex Baldwin is at his best as Jasmine's husband Hal, Peter Sarsgaard (who was brilliant in Lovelace, jeez can this man act) is great again as Jasmine's new beau Dwight, Louis C. K. takes a break from being an ace stand-up to be great as Al and even Andrew Dice Clay (not a man I'd ever choose to spend time with) is great as Ginger's ex-husband Augie.
There's basically not a bad performance here.
I think one of the reasons Blue Jasmine is so good is because half of it is set in New York. Allen has stopped making the setting of his films the centrepiece (Paris and London being the recent excursions), and returned to what he knows - using his home town as the backdrop to great story telling.
Yes, there's a bit of a return to the lingering scenic shots around San Francisco, but by then you're so wrapped up in these people's lives that you don't care. And such shots don't overstay their welcome.
Perhaps the most amazing thing about Blue Jasmine is how little of 'Woody' there is. Since having decided to stay behind the camera, he's still needed people to play 'him', the nervy, neurotic chatty character. In recent times it's been Owen Wilson's gig, but he's nowhere to be seen here.
As a result, a certain weight is lifted, and each character is allowed to shine on their own.
Yes, OK, there's still some of the old Woody kicking about - mainly shown through Jasmine here - but that was always going to be the case. The difference this time is it doesn't overshadow the whole film.
It's also fascinating to hear a woman's take on her husband's infidelity with a teenage girl. You can only take so much Woody Allen out of a Woody Allen film...
There's already Oscar mutterings around Blue Jasmine, and if Blanchett isn't nominated it'll be shocking - but Hawkins deserves a nod too, as does Allen himself.
He's created a real world again, with real people who have real lives and real problems. And he's back to making you laugh and wince and cry in equal measure.
This could easily have been called Woman On The Edge Of A Nervous Breakdown. Or Woody Comes Home(ish). This could even be the Woody Allen film that non-fans actually like.