Look up “ambitious” in the dictionary and you’ll see a poster for Cloud Atlas, a movie that makes The Fountain look like a Disney film. Based on David Mitchell’s 2004 sci-fi novel, Cloud Atlas has multiple characters of multiple ethnicities and multiple genders played by the same people (Tom Hanks, Halle Berry, Hugo Weaving) across six eras in time. People made fun of it when it came out, but we’ll tell you the true-true: Go with the flow of the Wachowskis’ three-hour saga and you’ll find that decoding the minutiae of each story is less rewarding than paying attention to the bigger picture.

If its unfortunate release date right after 9/11 wasn’t enough to insure that the now-cult classic Donnie Darko wouldn’t hit the box office heights, maybe it was the topic of grave mental illness and that TERRIFYING GIANT RABBIT. Oddly paced and oblique, with themes of time travel and the apocalypse, Donnie Darko (and its ending) is one of those movies people wrote theoretical treatises about because it was so obtuse. Watch again today and you might be astounded at how prescient it is, complete with end-of-the-world forecasts and Karens screaming about books in school.

This Oscar-winning Best Picture is still fresh in our minds, but it definitely deserves a place on this list (how many of us did rewatch it after it won all those awards?). EEAAO is a wacky, brilliantly discombobulated existential ride with absurd set pieces—hello, hot dog fingers and googly eyes—a hilariously weird Jamie Lee Curtis, and an emotional punch at the end. All at once, while you’re deciphering who is doing what, when, where and why, you’re getting a deeper message about embracing life and love in the present; at the very least, watching it again might help you understand that whole Raccacoonie thing. Fun fact: Jackie Chan was originally tapped to play Evelyn Wang.

David Fincher’s adaptation of Chuck Palahniuk’s nightmarish but darkly funny 1996 novel hewed pretty closely to the source material, until the Hollywood ending and that iconic twist. Moviegoers weren’t into its chaos and toxically masculine violence—despite the good time to be had watching Edward Norton and Brad Pitt punch the bejesus out of each other—and it failed at the box office. However, Fight Club put up a fight on DVD, becoming one of 20th Century Fox’s biggest successes simply because millions weren’t quite sure how the Narrator became so unreliable at the end (and yeah, the fight scenes totally hold up, too).

Director Darren Aronofsky isn’t one to shy away from tough subjects (see: Requiem For A Dream, which made our recent list of movies you only need to watch once), and religion is no exception. The Fountain is a nonlinear trinity of stories spun from the main plot of a doctor trying to save his dying wife. It features Hugh Jackman and Rachel Weisz as a bonded couple trying to defeat death across time and space. Critics were meh and audiences hated it, finding the narrative-inside-a-narrative and the recurring motifs too convoluted. But that’s why you should revisit this gorgeous film about grief and resolution. And to see Hugh Jackman ugly-cry again.

Inception, Christopher Nolan’s popular yet confusing mindbender, became one of the most cerebral recent blockbusters to come out of Hollywood. If you don’t recall, Leonardo DiCaprio stars as a thief tasked with implanting ideas into a target’s subconscious to steal information—but this basic plot line is of less importance than the idea of exploring the metaphysics involved in creating and layering dreams into someone’s brain. By the time it’s over, you wonder what ideas have been implanted in yours, and that rewatch becomes both necessary and entertaining.

Interstellar, Christopher Nolan’s nearly three-hour space epic, might have felt like a beautifully grueling watch the first time, thanks to its college-level astrophysics explanations and highbrow take on humankind’s purpose. If you saw it with a friend, you probably discussed it for days afterward. And like Kubrick’s mind-bending 2001: A Space Odyssey, it calls for a second look to figure out what the heck’s going on. Even if you still don’t get it, go with the flow, enjoy Matthew McConaughey’s brilliant performance as a NASA pilot hoping to save the world, and the jaw-dropping visuals that accompany Hans Zimmer’s score.

David Lynch described Lost Highway as a “psychogenic fugue,” and we’d be inclined to agree if we knew what that meant. The surreal plot has to do with two crisscrossing stories: one about a cuckolded jazz musician who suspects his wife is cheating, the other about a man drawn into a bad situation by a femme fatale cheating on her gangster boyfriend. The kicker is that both women are played by Patricia Arquette. The protagonists switch places midstream, Arquette is forced to strip down in front of a bunch of men, and someone gets murdered (or do they?) in this skeevy soft-core noir that even critic Roger Ebert said was futile to try and understand. And he watched it twice. But you might as well try to watch it again, if only for that fab Lynch aesthetic.

Most of Paul Thomas Anderson’s movies can be described as “ambitious,” a word that can be used alongside “pretentious” and “overstuffed” to describe this sprawling story about intersecting lives in Los Angeles. It’s a movie that critics ate up, but audiences didn’t (Cinemascore gave it a C-). Magnolia will be an epic, challenging three-hour rewatch that you may love or hate the second time around, but at least you might catch a few clues about what those damn raining frogs mean (look for some biblical signs, literally and figuratively, throughout).

It should come as no surprise that the neo-noir mystery thriller Memento is one of several Christopher Nolan films on this list, with its told-in-reverse twists and turns and exploration of how memory can be the ultimate deceiver. Guy Pearce (’memba him?) stars as an amnesiac trying to track down his wife’s killer using tangible things like photos and tattoos to capture information he’d immediately forget. There are entire diagrams devoted to plotting out the structure of the film, which in most other directors’ hands would be an unintelligible mess, but Nolan deftly guides you through it to the finish, where the story ends—or does it?

David Lynch’s frustrating cinematic masterpiece of neo-surrealism was originally supposed to be a TV series on ABC and was shot as a 90-minute pilot that execs declined to pick up to series. All the better for movie fans, as Lynch was free to drop extra characters and scenes and change it however he wished. Like all things Lynchian, Mulholland Drive is maddeningly elusive, a mystery that necessitates multiple viewings. But rather than feeling like homework it’s more like listening to your favorite album. Enjoy the cinematography, the tingling sensation of déjà vu, and the discovery of all the things you missed the first time.

Pi was Darren Aronofsky’s first feature, and a whopper of a debut at that. Max (Sean Gullette) believes numbers hold the secret to all things. He’s a math savant, but also a creepy loner on the verge of insanity who hangs out with his elderly buddy playing games and discussing the mysterious 216-digit number spat out by his junky old computer. Since math isn’t every moviegoer’s cup of tea, maybe you wrote it off as a too-intellectual art film shot on too-vivid black-and-white reversal film. But on second look the plot—told from the viewpoint of an unreliable narrator—is pretty straightforward, and its ending begs for another watch.

Ready for a cerebral workout? Low-budget indie Primer was made for nerds, and filmmaker Shane Carruth (a former engineer with a math degree) opted not to dumb down its technical dialogue and paradoxical timelines for the audience. Some 45 minutes into the movie, after much scientific mumbo-jumbo, we learn that the two main characters (engineers, natch) have built themselves a time machine that has catastrophic implications. Cue the repeat time traveling, multiple story loops, brain-teasing logical conundrums, and vague ending that only the hardiest of us have the mental cojones to revisit. That’s you, right?

Moviegoers hoping for a straightforward Alien sequel probably didn’t expect to be confronted with heady, philosophical questions about religion and the meaning of life wrapped in a violent Ridley Scott sci-fi horror film. At its most basic, Prometheus explores the eternal question, “where did we come from?” while serving up plenty of violent action and gnarliness (at least this time you’ll know when to cover your eyes during Noomi Rapace’s big surgery scene). Why some people do very stupid things may not be the question you’ll find an answer to in Prometheus, but at least the film is pretty to look at twice.

Stephen King famously loathed director Stanley Kubrick’s adaptation of his supernatural potboiler about a family torn apart by violence because it changed so much, including the ending that hones in on a particular photograph. Not only do we recommend rewatching The Shining because it might be the best horror movie ever, but because it’s necessary to enjoy the conspiracy theory-laden documentary about the film, Room 237. Is the Overlook Hotel a CIA setup or is it Hell? Did Wendy imagine the whole thing? Is it all a Holocaust metaphor? It’s a compelling good time watching it with these weird theories in mind while searching for Kubrick’s face Photoshopped in the clouds.

Shutter Island, the fourth team-up between Leonardo DiCaprio and director Martin Scorsese, is about a World War II-era U.S. marshal investigating a missing psychiatric patient while secretly hoping to avenge the death of his wife at the hands of another inmate. He travels to the ominous Shutter Island hospital for the criminally insane where he meets two doctors—one has empathy for his patients, the other has none—and as they help with the investigation the marshal experiences some disquieting flashbacks of his own. Scorsese delivers a cool noir thriller with elements of psychological horror that works all the way to the ending you’ll never have seen coming, which is why it’s worth a repeat viewing.

Why are we including this thriller that put twist ending king M. Night Shyamalan on a list of movies to rewatch, when by now you already know its killer conclusion? First, to appreciate Bruce Willis’ terrific, tragic acting and Haley Joel Osment’s heartbreaking performance. Second, because another viewing will allow you to parse out the clues of that probably should have smacked you in the face the first go-round. The Sixth Sense is a devastating ghost story about sad and lonely people that has a killer surprise–the movie is the near-perfect dragon that Shyamalan’s been chasing ever since.

Director Andrei Tarkovsky hated 2001: A Space Odyssey so much he came up with this answer to it—a thought-provoking and meditative exploration of the human soul based on the 1961 novel of the same name. If 2001 was the technology-focused, special-effects positive, then Solaris is its messy negative, less concerned with explaining the science than examining the human condition. Tarkovsky isn’t for everyone (the opening scene is five silent minutes of a guy strolling in nature) but by the end, things come full circle and that scene becomes clear—all the more reason to watch it again. (To better understand Tarkovsky’s unique filmmaking style, it’s not a bad idea to read his book, Sculpting In Time).

Dwayne Johnson stars in Southland Tales from Donnie Darko director Richard Kelly. The film is set in a dystopian near future after a nuclear attack on Texas starts World War III and something called “Fluid Karma” is ripping holes in the space-time continuum. Kelly based the movie on graphic novels he wrote while filming, a process he said pushed him “to the edge of my own sanity”—the same feeling most critics and audiences had while watching it—but it’s worth another look for the star wattage (including Sarah Michelle Gellar, Janeane Garofalo, and Kevin Smith).

Long before Kevin Spacey’s legal troubles, he rose to acclaim in the ’90s for movies like The Usual Suspects. Spacey plays the ultimate boogeyman, the mythical super-criminal Keyser Söze, whose reputation for psychopathy precedes him—at least according to con man Verbal Kint. Upon rewatching it, you’ll see the “gotcha” ending is actually the whole point of the film; pay attention to the artist’s sketch of Söze and the bulletin board in the detective’s office for clues to the Big Reveal. The film—which won an Oscar for Best Original Screenplay and Spacey won for Best Supporting Actor—still holds up today.