1. Plan 9 from Outer Space (1959)
Ed Wood tackled extreme concepts with no budget and made it work any way he could. I admire that trait. That doesn’t mean it’s not hilarious to watch things go awry, like seeing the set shake when the door closes or the boom mic dip down into a shot.
2. Johnny Suede (1991)
It doesn’t know whether it’s a drama or comedy, but it charmed me in the way a lot of uncompromisingly unusual movies do. There are a lot of moments in the movie that kept me watching it over and over, like one of the funniest crying attempts I’ve ever seen.
3. Showgirls (1995)
From its very first scene, in which Nomi (played by Elizabeth Berkeley) ineptly pulls a knife on a pervy truck driver, you know you’re in catastropheland.
4. Deadly Premonition
The story in this game involves an FBI agent investigating a murder in a small town that seems ripped off from “Twin Peaks”—but it is way, way weirder. It’s also an ambitious open-world game filled with nothing to do but fish, talk to weirdos, shave and get your clothes dry-cleaned.
5. The Room (2003)
The Room made $1800 at the box office and closed after two weeks. One reviewer said that watching The Room was like “getting stabbed in the head.”
When I decided to write a book about my experience making The Room—the worst movie ever made (really)—I wanted to approach it differently from how so many before me came to it. I wanted to take this cinematic catastrophe and turn it into something in which comedy and drama, sadness and happiness, shock and familiarity all constantly duked it out.