Megan McArdle nominates Far & Away and The Road to Wellville for the title, based on the following criteria:
To qualify as one of the worst films of all time, several strict requirements must be met. For starters, a truly awful movie must have started out with some expectation of not being awful. That is why making a horrific, cheapo motion picture that stars Hilton or Jessica Simpson is not really much of an accomplishment. Did anyone seriously expect a film called The Hottie and The Nottie not to suck? Two, an authentically bad movie has to be famous; it can't simply be an obscure student film about a boy who eats live rodents to impress dead girls. Three, the film cannot be a deliberate attempt to make the worst movie ever, as this is cheating. Four, the film must feature real movie stars, not jocks, bozos, has-beens or fleetingly famous media fabrications like Hilton. Five, the film must generate a negative buzz long before it reaches cinemas; like the Black Plague or the Mongol invasions, it must be an impending disaster of which there has been abundant advance warning; it cannot simply appear out of nowhere. And it must, upon release, answer the question: could it possibly be as bad as everyone says it is? This is what separates Waterworld, a financial disaster but not an uncompromisingly dreadful film, and Ishtar, which has one or two amusing moments, from The Postman, Gigli and Heaven's Gate, all of which are bona fide nightmares.As a teenager I voluntarily and repeatedly watched both of her nominees, albeit on cable. To be sure, both are terrible. But the worst ever? Far & Away was the Titanic of its time; twelve-year-old girls are not discerning, and the film didn't expect its audience to be. And The Road to Wellville, for those of us who read and enjoyed the Boyle novel on which it is based, is a fascinating train wreck of a film that fails utterly as cinema but does succeed in capturing some of the profound weirdness of the book. As a bonus, it offers us the pathetic spectacle of Dana Carvey dressed as a hobo, clawing desperately for the film success that would later come so easily to his SNL partner, Mike Myers.
Six, to qualify as one of the worst movies ever made, a motion picture must induce a sense of dread in those who have seen it, a fear that they may one day be forced to watch the film again - and again - and again.
I nominate Even Cowgirls Get the Blues, although I'm not sure how well it meets criterion #5. There's probably something out there I haven't seen that wins the prize (my money is on a movie from Robin Williams's "I IS A SRS ACTOR" period).