Daniel Drezner points to this Joe Queenan essay:
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.
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. To pass muster as one of the all-time celluloid disasters, a film must be so bad that when a person is asked, "Which will it be? Waterboarding, invasive cattle prods or Jersey Girl?", the answer needs no further reflection. This phenomenon resembles Stockholm Syndrome, where a victim ends up befriending his tormentors, so long as they promise not to make him watch any more Kevin Smith movies. The condition is sometimes referred to as Blunted Affleck.
I don't think that can be quite right--is waterboarding really objectively better than invasive cattle prods? But I take the general point.
Dan nominates Caligula; Alex Massie goes for the Sicilian. I'm torn between Far and Away and The Road to Wellsville. I saw the latter with my then boyfriend, who was the son of an economist. Ten minutes into the movie, he said "Let's go."
I demurred. "We paid three dollars for these tickets. I'm going to watch the movie."
Ten minutes later, he whispered more urgently "Come on, it's just getting worse. Let's go."
"No," I insisted, "I am not wasting three dollars on twenty minutes of movie."
The rest of the movie passed in a sort of a nightmare that has become associated in my mind with Mark Twain's description of opera:
The banging and slamming and booming and crashing were something beyond belief. The racking and pitiliess pain of it remains stored up in my memory alongside the memory of the time that I had my teeth fixed
By the time the lights went up, we were the only people in the theater. This on a Saturday night.
My boyfriend looked at me and said "I'm taking you to meet my father."
"Because someone needs to explain the concept of sunk costs to you."