It's a good list you provided, and a tough question... With any other filmmaker it would be a relatively straightforward task, but Woody Allen has assembled so many gems in so many different styles that finding the essential five above all the others... Hmmmm.
OK, here's my list (for today - I'm sure it'll be different six months from now). Based on the reward I had of watching the movies repeatedly:
1) Annie Hall
2) Manhattan
3) Celebrity
4) Hannah and her Sisters
5) Deconstructing Harry
but very close (too) to the fifth position, so I feel OK only if I can mention 9 or 10:
Crimes and Misdemeanors
The Purple Rose of Cairo
Hollywood Ending
Alice
Interiors
Yes, I know that the last mention is the black sheep here, but 'Interiors' is probably the best Bergman-like movie that was not made by Ingmar, and it is a small masterpiece in its own right and genre.
There are a LOT of cute, likable, pleasant movies by Allen that I still like, but that have not stood the test of time as well as the 10 above. So I rarely feel like watching movies such as Shadows and Fogs, Radio Days, Broadway Danny Rose, Zelig, etc. again, although I truly liked them at the time.
I simply adore Woody Allen, but just like any other genius, he does sometimes release material that is still better than 75% of the rest of the industry, but not quite up to the level we are acquainted to.
So genre is my list of the 5 MOST FORGETTABLE (I prefer this to "worst") movies by Woody Allen, in no particular order:
1)Mighty Aphrodite:
some funny scenes, but the relentlessly shrieking voice of Mira Sorvino (on purpose, I know, but yet agonizingly painful to the ear) is too much for me, let alone the fact that Woody in the role of dating counselor ??
2)Bananas
Goofiness at that level has not aged well for me...
3)September
Too bleak, even glaucous...depressing (Interiors may also be depressing sometimes, but only in a good way and for a good purpose)
4)Bullets Over Broadway
Without Woody's presence, the humor in it does not stand repeated viewings for me. Other Woody-less Allen's comedies stand better, probably because there is a good Woody-like character (like "Celebrity" for example, where Kenneth Branagh is simply brilliant !
5)Another Woman
Granted, Gena Rowlands is simply stellar in a difficult role but the tone of the movie, especially with the constant narration, is too literary and sounds artificial to me. One wishes the elitist atmosphere that completely submerges Marion's existence would sound more natural. This is where Woody the writer sometimes fails as a director: he may be too satisfied or like too much his own script to have the right perspective to transpose it to film and get rid of the pseudo-intellectual references and style of his writing. In such cases, yes, I do think that Woody would have needed someone's input as a director to improve his already good screenplay into excellent movie direction. It's hard to always be top notch in both writing AND directing, and his achievements in this respect are already extraordinary.
In a way, Woody Allen has spoiled us so much with so many masterpieces that inevitably, one feels bad having to point out that they have rare but definite shortcomings. Same problem with directors like Hitchcock, Lynch or Burton, whom I also adore to a high degree, but who have sometimes, on rare occasions, disappointed me.
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