Usually to suggest that a director’s films exist within a league by
themselves is high praise—an accolade best bestowed upon only the
most revered architects of the craft. And while this is certainly true
of Woody Allen, the fact that his films stand alone has less to do with
his talents as a filmmaker and more with the self-contained/endlessly
constrained aesthetic he’s honed annually over the last 30-some years.
Woody Allen’s movies are removed from—and thus, for better and
often worse, somehow scarcely comparable to—anything besides
other Woody Allen movies. Which is to say that, while it’s generally
accepted that Woody Allen has made a shit-ton of terrible films, he’s
only actually made a few terrible Woody Allen films.

When compiling a list of the worst films in Woody Allen’s ample
catalog, the first instinct is to gravitate toward his oft-maligned
chamber dramas—the largely unredeemable trio of Interiors,
September, and Another Woman. These only really
half-qualify though, as they’re more accurately Woody Allen’s bad
Ingmar Bergman movies than bad Woody Allen movies. To reach the true
dregs of Woody’s work, one must saunter past the sometimes boring but
largely innocuous ’80s and into his first true creative
drought—an early ’90s that saw the consecutive releases of
Alice and Shadows and Fog, Allen’s first truly bad Woody
Allen movies. Fortunately, he followed it with the pretty good
Husbands and Wives, after which he managed to dither between
mediocrity and quality until the end of the decade. Then shit got
really bad.

Despite the slight reprieve of Sweet and Lowdown in 1999,
Woody managed to dish out the very worst films of his already spotty
career in rather quick succession: Celebrity (bad), Small
Time Crooks (worse), The Curse of the Jade Scorpion (even worse), Hollywood Ending (fuck!), Anything Else (not that bad), and Melinda and Melinda (fucking
dreadful). It was only after he made the distinctly non-Woody
picture Match Point that he managed to get out of the
hole—which, seeing as how his latest, Cassandra’s Dream, comes out this week—is hopefully a lesson learned.