The 13 Strangest Movies We’ve Ever Seen

Riding high off the success of the previous collaboration, the lovely Jerry Maguire, writer-director Cameron Crowe and star Tom Cruise could do almost anything they wanted — and opted to remake the fascinating 1997 Spanish film Abre Los Ojos (which translates as Open Your Eyes), and to do it with one of that film’s stars, Penelope Cruz.

Both are deliciously bold and strange films, but Vanilla Sky is especially daring, shifting from a complicated romance to serious sci-fi. We don’t want to give too much away, but this is a movie that finds room for a visual shoutout to a 1963 Bob Dylan album, a discussion of your favorite Beatle, and a song by one of those Beatles. It’s one of the strangest movies, but is also, oddly, a comfort watch.

It also features a very good Cameron Diaz and Kurt Russell.

Just before remaking Open Your Eyes, Tom Cruise collaborated with Stanley Kubrick on this, his other strangest movie — and one that also prominently features masks. No one who has seen Eyes Wide Shut can say exactly what happens, or who is who.

The rhythm is somnambulant, befitting of a movie based on a novella called Dream Story. Kubrick initially envisioned Steve Martin or Woody Allen starring in his adaptation of Arthur Schnitzler’s 1926 story, and the casting ideas hint at the film’s comic roots — though everyone plays everything very seriously, or perhaps melodramatically.

The film’s strangeness is compounded by the meta drama of the relationship between Cruise and Nicole Kidman, his real-life wife at the time, during an unexpectedly long and complicated shoot. Kubrick died just before the film was released, leaving no one to explain what Eyes Wide Shut means — not that Kubrick ever would have. We think about this film all the time, trying to sort out the precise qualities that make it one of the strangest movies, and most impressive.

Todd Haynes’ Superstar: The Karen Carpenter Story is a biography of The Carpenters’ singer Karen Carpenter, including her tragic 1983 from heart failure due to complications from anorexia. If that sounds straightforward, it’s because we left out a key detail: It’s all acted out with Barbie dolls.

It was pulled from release after a copyright infringement lawsuit filed by Karen’s brother and musical partner, Richard Carpenter, who objected to the use of The Carpenters’ songs.

If you think the film sounds disrespectful, it’s not: The film is deeply empathetic toward Karen and admiring of her artistic legacy, and the use of the dolls feels like a commentary on Karen being manipulated and objectified. But Richard and his and Karen’s parents are decidedly unlikable in the film, which may explain Richard’s objections to Superstar.

A very DIY, very microbudget movie about depressed thrill-seekers who seek out the exciting new high of… worms.

Director Alex Phillips and a team that includes producer Ben Gojer, who created the film’s unsettling creatures, fills the screen with horrible behavior, but uses all the tools of moviedom — the expectation of catharsis, uplifting music — to make us root for people we know we shouldn’t be rooting for.

It’s easily one of the strangest movies we’ve ever seen, but but also an intoxicating cinematic experiment.

The debut film from Boots Riley, leader of the brilliant rap group The Coup, stars LaKeith Stanfield as Cassius “Cash” Green, a young Black man who starts to excel at his telemarketing job when he begins adopting a white phone voice (a dubbed-in David Cross).

None of the above is what makes it one of the strangest movies we’ve ever seen.

Things get weird when Cash starts investigating what is company actually does… and we aren’t about to spoil it for you here. Suffice it to say it’s one of the wildest twists in any movie.

Before he gained much deserved acclaim for films like Carrie, Scarface and The Untouchables, Brian De Palma was best known for scrappy experimental films like Hi Mom and Sisters. The Phantom of the Paradise was an apparent attempt at a commercial breakthrough. But some audiences were weirded out by its garish ambience, and some jaded critics considered it a ho-hum satire of the music industry.

In retrospect, it’s simply one of the strangest movies we’ve ever seen — and one of the coolest. Music producer Swan (Paul Williams, who also provides much of the haunting music) makes naive songwriter Winslow Leach (William Finley) sell his soul and his songs so that they can be performed by Swan’s pet protege, Phoenix (Jessica Harper). He seeks justice by becoming The Phantom of the Paradise.

The atmospherics are incredible — doomed and portentous, without ever veering fully into camp. It’s also fun to note that Williams would, just a few years after this, co-write “The Rainbow Connection” for Kermit the Frog — and to wonder if, considering that De Palma and George Lucas traveled in the same circles, The Phantom influenced Darth Vader.

People who think movies are too safe today just aren’t watching enough indie movies. This Canadian horror hit, made for about $10,000 in U.S. dollars, features just four actors, and follows the perspective of small children whose parents have disappeared. Then other things disappear, too: windows, doors, a toilet.

It tries to make you experience time the way it passes for a child — have seconds gone by? Or years?

Demanding your full attention, it’s very divisive, to be sure: Many viewers find that the only way to fully appreciate it is in a theater, with others going through the same baffling experience. It’s part horror movie, part art exhibit, and one of the strangest movies we’ve ever seen.

What is Donnie Darko about, exactly? Richard Kelly’s masterpiece follows Jake Gyllenhaal as a troubled teen haunted by a man named Frank in a rabbit suit — or is it a suit? — who informs him that the world will end in 28 days, 6 hours, 42 minutes and 12 seconds.

With a stacked cast including  Jena Malone, Maggie Gyllenhaal, Drew Barrymore, Mary McDonnell, Katharine Ross, Patrick Swayze, and Noah Wyle, Donnie Darko is worth watching just to see who will appear next. But it also works on your psyche, especially when you watch it knowing that it premiered ahead of the Sept. 11 plane attacks. It feels very much like the end of the dream of the ’90s.

We don’t claim to understand it, but we never doubt its commitment to Sparkle Motion.

Speaking of rabbits… sure, Who Framed Roger Rabbit was the biggest hit at the box office in 1988. But it’s also one of the strangest movies we’ve ever seen, and probably the strangest movie to become a huge commercial success.

It takes the old Disney trick of combining live-action with cartoons, but does it as a straight-out noir, complete with a va-va-voom femme fatale, Jessica Rabbit (voiced by Kathleen Turner). On top of that, there’s a fairly complicated (and kind of accurate) conspiracy theory at the heart of it about turning Los Angeles into a city ruled by cars.

It’s also filled with dark humor, like the joke about sending poor Roger “back to the science lab.” We love Roger Rabbit, one of the strangest movies we’ve ever seen, and a movie that opened our young minds to all kinds of possibility.

We like everything Paul Schrader does, but couldn’t be more surprised that he followed up 1980 — a year when he wrote Raging Bull and wrote and directed American Gigolo — with the sensationalist in the best sense Cat People.

After opening with a women being sacrificed to a black panther, the film cuts to modern (in 1982) New Orleans, where strange things are afoot at the zoo. Meanwhile the innocent Irena (Nastassja Kinski, above) reunites with her brother Paul (Malcolm McDowell), and a string of cat-adjacent murders.

Then things get much stranger from there. You’ll never look at your cat the same way again.

The newest film on this list — it’s in theaters now — stars Vera Drew as a struggling performer who becomes someone called “Joker the Harlequin” to dismantle the comic tyranny of Batman and Lorne Michaels, who is kind of like the Lorne Michaels who created Saturday Night Live, but different.

The film has layers of metaphor — the search for a comic identity parallels Vera’s coming out as trans — and it’s loaded with inside jokes about Batman, but also about alternative comedy and singer-songwriter Ben Folds. It’s very funny, and — here’s the unexpected part — igorgeous. Drew enlisted a team of friends to create her own beautiful version of demented Gotham.

The parody of Warner Bros. characters drew a legal warning from the studio when it premiered at the Toronto International Film Festival, but no one would ever mistake The People’s Joker for a studio film. It’s completely independent and original, and one of the strangest movies we’ve ever seen, in all the good ways.

No list of the strangest movies we’ve ever seen would be complete without at least one film by David Cronenberg, the king of body horror whose obsessions are perfectly encapsulated in Videodrome.

We have no idea how to explain what happens in this film, released during the rise of home video, expect to say that it fascinatingly anticipates reality TV, the internet, and VR and AR advancements that meld humanity with technology, never more directly than when James Woods’ character, Max Renn, inserts a Betamax tape into his torso.

We also love Blondie singer Debbie Harry (above) as the mysterious Nikki Brand.

The strangest thing about Mulholland Drive, arguably David Lynch’s best movie, is that it seems almost conventional, at the start. Naomi Watts plays an aspiring actress, Betty Elms, who turns out to be shockingly good. She goes with Rita (Laura Harring), who has amnesia, to look for a woman named Diane Selwyn, because Rita remembers her name.

But soon Watts is playing Diane, And Rita is Camilla. But so is Melissa George. The mafia is involved. Billy Ray Cyrus pops up in the role of Gene.

Lynch has refused to explain what it all means, but the original DVD release did include a card containing “David Lynch’s 10 Clues to Unlocking This Thriller.” Among them: “Pay particular attention in the beginning of the film: At least two clues are revealed before the credits” and “Notice appearances of the red lampshade.”

It would be easy to fill this list with David Lynch movies, but we’re opting to go with the one we like best. At least today. Suffice it to say that almost anything he’s made — except for The Straight Story — would fit easily on a list of the strangest movies we’ve ever seen.

Thanks for reading our list of the strangest movies we’ve seen.

You might also like this list of Eye-Popping 1950s Movie Posters or this interview with Vera Drew, creator of The People’s Joker.

Editor’s Note: Corrects main image.