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.