Matt Abra, CONTRIBUTOR
59) The Sixth Sense (1999)
Some of us guessed the ending (and have been holding it over people ever since), but the fact that The Sixth Sense is, to us, still a haunting and sad fable of quiet redemption goes to show that famous “surprise” was just gravy. The whole thing is slowly mesmerizing, and scary in all the right places.
58) Good Will Hunting (1997)
Try watching Good Will Hunting without then spending hours insulting your friends with a rowdy Boston accent. No? Okay, fine, you’re better than us. But also don’t forget that it’s smart, it’s funny, it’s heartbreaking—it rings of life.
57) The Lives of Others (2006)
The first foreign language film to grace our list (and the Oscar winner in that same category), The Lives of Others is a carefully constructed and quiet spy film, and what it lacks in Bond-esque car chases it makes up for in subtle chills, carefully administered through Ulrich Mühe’s haunting performance.
56) The Longest Day (1962)
Is it the greatest war movie ever made? If you don’t think so, you at least have to admit it’s the most ambitious. At three hours long, with dozens of characters and unceasing battles, the grandeur of the Second World War has never been better represented.
55) Juno (2007)
As Jon Stewart noted as host of the Oscars, “Thank God for teen pregnancy.” At a time when Hollywood suddenly and inexplicably turned dark dark dark (No Country For Old Men, There Will Be Blood, and the list goes on), Juno was a funny, honest, and endlessly sweet piece of levity, and it may have saved our souls.
54) The Departed (2006)
Martin Scorsese finally won his Oscar for this amped up crime saga, and, nice for him, it wasn’t merely a make-up win, it was more than deserved. In perhaps Leonardo DiCaprio’s most underrated performance, he plays an undercover cop who gets caught up with some shady stuff in Boston’s mob world. Then again, watch the final 15 minutes to see why “shady stuff” is a gross understatement.
53) This is Spinal Tap (1984)
Insert obligatory joke about “turning it up to 11.” This is Spinal Tap is packed to the brim with cultish quotes about squashing dwarfs and licking love pumps, and if you’re not in on the fun, you’re missing out.
52) Se7en (1995)
Most people usually just think of that ending (and for good reason), but be reminded of its overall morbid atmosphere of unease, its showcase of a city—and world—in eerie disrepair. You kind of have to be a cynic to get optimum enjoyment from Se7en, so dare I ask, how could it not be a favourite of Millennials?
51) Rocky (1976)
In some ways, it’s a shame that Rocky was practically sequeled into caricature. I mean, you may love Rocky IV’s camp, but let’s be honest, Ivan Drago was a cartoon. The first go-around was, however, a glowing tribute to the human spirit, and like the best sports movies, it was actually about the people doing the punching, not just the punching itself.
50) The Grand Budapest Hotel (2014)
Wes Anderson reached his zenith with this quirky period piece, and he did it by, at last, perfectly mixing his signature visual delights with the human heart. Ralph Fiennes shines as a concierge who does side-work as a gigolo. His line readings are so perfectly aloof, he’s the scoundrel you can actually believe in.
49) The Lord of the Rings: The Return of the King (2003)
The Lord of the Rings Trilogy received its Best Picture Oscar for its third go-around, which many thought was a way to celebrate the entire nine hour epic, but we think it got special recognition because, on top of the breath-taking visual spectacle, the actors finally got to invoke full catharsis with their characters. At the peak of Mount Doom, the emotions reached their peak as well.
48) The Incredibles (2004)
. . . is incredible. With its first PG rating, Pixar amped up the intensity, and amped up the fun at the same time.
47) Vertigo (1958)
Some lists call it the greatest movie of all time. We didn’t go that far (to us, it’s not even Hitchcock’s greatest, as you’ll see), but given that the film’s portrayal of sexual politics and obsession are still timely today, Vertigo was a revelation in its time, and a darn suspenseful one at that.
46) Oldboy (2003)
With The Departed, Se7en, and now Oldboy, it would appear this portion of our list was reserved for all the downer endings. A newly heralded classic, South Korea’s Oldboy mesmerized audiences with its rowdy fight scenes, its hypnotic violence, and its disturbing—and disturbingly perfect—resolution. Try looking at a hammer the same way again after this.
45) Blade Runner (1982)
Sometimes reissues are actually a good idea (just not when George Lucas does them). A bit misunderstood when it first hit theaters, the stripped down director’s cut of Blade Runner made Ridley Scott’s mysterious, neo-noir futuristic thriller a deeper, and achingly human sci-fi masterpiece.
44) Casino Royale (2006)
Was it the most memorable James Bond film? It’s hard to tussle with the iconography of movies like Goldfinger or From Russia With Love, with their flying hats and explosive boat chases, but we’re going to call Casino Royale the BEST Bond film. Daniel Craig honestly deserved an Oscar nomination for how convincingly he mixed Bond’s steely resolve with a layered humanity that we’d hardly, if ever, seen in the character before.
43) Spider-Man 2 (2004)
Up there among the greatest superhero movies ever made, at this point what may be most appreciated about the second Spider-Man film is that the villain enhanced the story of Spider-Man, not the other way around. At the time, superhero movies tended to be about making the most impressive effects-driven antagonist. Here, Sam Raimi made both superhero and struggling young man equally compelling.
42) 2001: A Space Odyssey (1968)
It’s almost impossible to keep a classic film called 2001 from the Millennials List of Greatest Films, even if its slow-burn pace and difficult symbolism are not exactly what our generation is known for. Then again, a space-opera about the folly of mankind is right up our alley, so we’ll just put it on the list and move on.
41) Gladiator (2000)
In Hollywood, they don’t make them like this anymore. Except that they did! Inspired by the epic period dramas of the 50s and 60s like Ben-Hur and Spartacus, Gladiator updated it all for modern audiences, and while people, some of them desperately, tried to write the film off as popcorn splurge and nothing more, a Best Picture Oscar and Best Actor Oscar for Russell Crowe silenced them forever. This is popcorn as high art, and it’s majestic.
