#1. Alexander (2004)
Oliver Stone was so well-known when he made it that audiences weren’t exactly expecting a passion project out of him. In fact, nobody was expecting anything out of him. He hadn’t done a high profile movie since 1995’s Nixon, and had only done two other films since then. By 2004, he was pretty much known by reputation, which had been distorted to the point of irrelevance. Alexander was seen as just another misguided attempt to cash in on the success of Gladiator, a historical epic worth ignoring, or worse yes, outride deriding. He cast Colin Farrell, “who looked nothing like Alexander the Great,” in the title role, and submitted as supporting cast Angelina Jolie, Val Kilmer, and Anthony Hopkins, none of whom were all that popular at the time. Anyway, all of that negative talk is say that none of it really matters. Stone achieved his masterpiece twenty years into his Hollywood directing career. Farrell has never before or since found a role more befitting his unparalleled range, a sensitive actor who can also command the screen, whose singular knack for conveying desperation goes a long way in exploring the scope of a life that made history through sheer force of will. Kilmer and Jolie are indispensable in filling out this portrait, demonstrating equally powerful figures who help shape the man Alexander becomes, just as Hopkins explains his legacy for people who might still not get it. There are three cuts, the final one presenting a definitive version, but you really can’t go wrong whichever way you go. If you look past all the bad press, though, the movie really ought to speak for itself. Simply put, the most powerful movie I have ever seen.
#2. Munich (2005)
Steven Spielberg was in a fairly similar position as Stone when he made this portrait of terrorism. By all records, he’d already made all the definitive career statements any handful of directors could have been expected to make, a wide gamut from E.T. to Schindler’s List. Most of the critics at the time were looking for a movie that explained the modern world, post-9/11, and mostly, they looked to war stories. When Spielberg delivered this look back at the Israeli reaction to the Munich Olympics murders, it looked more like an homage to classic thrillers than a nuanced picture that blamed no one and impugned everyone. Most people hate that sort of thing. They prefer black and white. To personify the message, he cast Eric Bana, one of today’s finest actors, but who has consistently failed to capture critical acclaim. His only problem is that same kind of vexing nuance.
#3. The Truman Show (1998)
I guess at this point you’ll begin to see a pattern forming. Nothing should be obvious. Here is Jim Carrey’s finest transformation to date, a perfect reflection of the comedian’s dilemma. Yes, he’s the center of attention, but that’s not really what he wants. All he wants is for his world to make sense. As it turns out, the way in which he does that is tremendously entertaining. The Truman Show is not only that, but also incredibly moving, a breakthrough reflection on reality TV before it really exploded. The only man the whole world wanted to watch actually had no idea. Nothing was fake about him except the circumstances cast around him. I guess that also describes everything reality TV did in the years that followed.
#4. The Dark Knight (2008)
Christopher Nolan quickly established himself as the most cerebral filmmaker of his generation. Early films like Following and Memento relied on a certain amount of gimmickry, but soon he set out to prove that his flair for getting attention was just the icing on the cake. Tackling superheroes had become something of a hobby for established directors like Bryan Singer and Sam Raimi in recent years, but it took Nolan to truly embrace them. He gave Heath Ledger the defining role of his career, which finally transformed him into a character actor, and in doing so, perfectly encapsulated the murky portrait of modern heroism, super or not.
#5. The Assassination of Jesse James by the Coward Robert Ford (2007)
Brad Pitt has such an abundance of charisma, he makes a curious icon of modern cinema. He never does what he’s supposed to. The actor everyone mistakes for Brad Pitt is Johnny Depp, but it’s Pitt who is constantly searching for the roles that fulfill him artistically, rather than the ones that are showy. It’s Pitt who’s perfect to casually inhabit someone who was genuinely infamous, who will instantly make you sympathize with someone who might at best be called an anti-hero, only to remind you in the least expected moments what kind of person he really is. Like Alexander, it’s a true story with constant surprises, the ring of truth behind high art, and has been all but completely overlooked. That’s the real tragedy.
#6. Inglourious Basterds (2009)
Quentin Tarantino arrived on the scene and was instantly acclaimed as one of the most exhilarating new voices in cinema, someone who was literally born into it. Then everyone got a little too used to him, even though he made more films almost as a last resort. This is beyond a doubt his masterpiece, combining both his instinct to throw what appears to be utter nonsense onto the screen, as well as his singular voice, the one which intrinsically understands great drama, merging into the sublime. This student has beyond a doubt graduated.
#7. Memento (2001)
This is how much I love Christopher Nolan. In previous versions of this list, this one was higher still, and has recently had the great privilege of being eclipsed by its own sibling. I imagine that if you want to make historical comparisons, Nolan is our Hitchcock, who envisions filmmaking to be no different than the best of literature, which can announce itself as much by what it says as how it says it. Even told front to back, this one would still work.
#8. Gladiator (2000)
Ridley Scott was another director well into his career when he made a creative breakthrough, coming into his own as a visionary of the historical epic, which he went on to practice with much success later. But the first in this instance is still the greatest, as he channels Russell Crowe into a reluctant hero, who even dies at the end, still clutching moral victory. It’s not an easy message to accept for those who would rather believe life is made to enjoy all of life’s rewards, even though those that are not technically earned, and so critics were always baffled by this one, even after it one the Oscar.
#9. Star Wars (1977)
The oldest film of the top ten and a full-blown cultural phenomenon, this one really needs no introduction. George Lucas perfects the sci-fi film here, and to this day no one has really tried to top him. The fact that five subsequent films further explain what the heck was happening in all that adventure, I can’t even begin to separate from its own impact. I was born three years after its original release. Remains the greatest story inspired by and created for film.
#10. JFK (1991)
Oliver Stone again, in the other film that has to be considered a masterpiece, the only piece of fiction that has attempted to tackle the most important moment in US history from the past century. To fully understand it, Stone exploits all the conspiracy theories behind the assassination of President Kennedy, only to explain why they’re physically necessary, and why the subject who isn’t even a character in the movie is still important today. My appreciation for JFK has grown over the years. This marks the first time it appears in the top ten.
#11. The Departed (2006)
The genius of Martin Scorsese is that he made a career thanks to Robert De Niro, but a legacy thanks to Leonardo DiCaprio. I know that sounds a little like heresy, but where De Niro inhabited characters in Taxi Driver and Raging Bull, it’s DiCaprio Scorsese captures literally at the moment he reaches acting maturity. That’s what this whole film is about. Titanic made him popular, but that didn’t guarantee Leo a career, as subsequent failures to capture the zeitgeist made clear. After The Departed, that all changed. Forget Blood Diamond, which somehow obscured his chances to win the Oscar for this performance. This is cinema magic, unqualified.
#12. The Matrix (1999)
The only movie that could possibly upset the public’s interest in Star Wars happened to debut in theaters just before The Phantom Menace. A strange combination of philosophy and action, The Matrix became ubiquitous in an instant. It wasn’t that its ideas were entirely original, but the way the Wachowski brothers presented them did. No matter what you think of the sequels, the first one burned an indelible image in movie history.
#13. Monty Python and the Holy Grail (1975)
The first out-and-out comedy on the list, it’s the kind of classic that ignores all restraint, understands no limitations of pretext, and puts it all out there, and pretty much everything sticks. You don’t need to be a fan of Monty Python to enjoy it, and I think that’s the one distinction that bothers most critics. You attach any label to the title, and that’s all they’ll think about. But in all seriousness, if Charlie Chaplin had done it, no one would be thinking that way today.
#14. Citizen Kane (1941)
This is the furthest back yet, and there’s a reason, because this is more or less the birth of modern cinema, from the consummate professional and genius of film, stymied by a system that had no use for any of that. They wanted Orson Welles, and they also really, really didn’t want Orson Welles, because in him was a talent that would not accept restrictions, and for that, the rest of his career was as constricted as possible. He better understood filmmaking than anyone else for the next twenty years. He was and still is far ahead of his time. He is Shakespeare and Herman Melville for a new medium. This is still his most famous accomplishment, mostly because it’s still so darned hard to find much of anything else that he did. It also happens to be really good. If it featured the famous actors of the day, more people would watch it.
#15. Watchmen (2009)
The comic book that looked beyond the episodic adventures typical of that medium, and instead looked at the scope of careers and history, became the next great superhero film in the hands of Zack Snyder. Famously described for years as unfilmable, Watchmen is actually the consummate film experience, full of set pieces and giant personalities, uncoiling moment after moment, until finally Snyder envisions a more perfect ending to the whole affair. I could kind of understand that after The Dark Knight, audiences weren’t quite ready to accept that someone else could make another superhero movie this good, but at some point, they are really going to have to catch up.
#16. Star Trek: First Contact (1996)
All of the Star Trek films will be on the list, but this ranking isn’t a de facto designation. I’m a Star Trek fan as well as a film fan, and this one is the best of the Star Treks, and also a great film, bolstered by Patrick Stewart’s embracing of the switch to the big screen. Like Star Wars a little earlier, I don’t know what someone would think if this were the only Star Trek they ever saw, but it was a pretty definitive success at the box office, so that’s probably a good indication that it works pretty well.
#17. Eternal Sunshine of the Spotless Mind (2004)
I saw this film as a fan of Jim Carrey, but there’s a wealth of other performances to enjoy, be it co-star Kate Winslet, or supporting actors Kirsten Dunst, Mark Ruffalo, Elijah Wood, and Tom Wilkinson, whose subplot could easily support its own great film. What’s so constantly surprising about this film is that it works on so many levels.
#18. Mr. Arkadin (1955)
Because of the conditions put on Orson Welles’ later career, as suggested earlier, I figure it’s up to personal experience as to the next best film in his canon. This one has been considered a weaker version of The Third Man, but I consider it a sort of tribute to Dostoyevsky, something that feels authentically Old World at times, but embroiled thickly in classic film noir as well. There are multiple versions available, owing to the fact that he was sabotaged in his attempts to put the finishes touches on the film. It’s your own reward to watch each of them, one of those tricks to have an excuse to rewatch a great film.
#19. Apocalypse Now (1979)
Almost from the beginning, Hollywood has been obsessed with the subject of war, trying to explain its horrors to a public that has not always been interested. Francis Ford Coppola famously took inspiration from a classic piece of literature, but that didn’t make it any easier to make. It was war to make this definitive portrait of war, defining the career of Martin Sheen, and giving Marlon Brando another chance to define his.
#20. The Usual Suspects (1995)
The problem with Bryan Singer is that he isn’t easy to pin down. If he’s got a particular message to make, he doesn’t make it very obvious, which may be one of the most refreshing moves a filmmaker can make. Here he makes a startling debut, building a web of characters out of a terrific cast, headlined by Kevin Spacey, in a role he still can’t top. Sometimes, when critics want to take the wind out a classic, they’ll try and explain its success away as some sort of fluke. There’s a reason why my appreciation for The Usual Suspects only grows.
#21. The Imaginarium of Doctor Parnassus (2009)
Terry Gilliam has been thinking out-of-this-world thoughts since he infiltrated the British brotherhood of Monty Python, but his uniquely American perspective has been formulating new fantasies for decades now, leaving him a prime candidate for critics to underestimate the longer he continues working. Here he guides Christopher Plummer into a profound exploration of legacy and responsibility. There are other things to talk about concerning this movie, but let’s concentrate of what it’s really about.
#22. The Mask of Zorro (1998)
For one generation, which was at this time well past its prime, pure cinematic adventure was embodied by Indiana Jones, just as it had once been by Errol Flynn. For me, it was this film, which had the good sense to dust off an old Hollywood favorite, and take it to a whole new level. Antonio Banderas, Anthony Hopkins, Catherine Zeta Jones, it was a potent combination, another funny little crossroads of careers, and the true birth of the modern cinema superhero.
#23. Dr. Strangelove: or, How I Learned to Stop Worrying and Love the Bomb (1964)
The name everyone associates with this movie is Stanley Kubrick, but I have two others that trump it: George C. Scott and Peter Sellers. Sellers is pretty obvious, so I’ll concentrate on Scott. I still have never seen Patton, so this is the experience that instantly explains Scott’s star power, his sheer presence, no matter the tone of the role. That’s a pretty good legacy, too.
#24. Star Trek (2009)
Here is the first time Star Trek really gets to just embrace moviemaking, because it’s the first time everything is created specially for the medium. J.J. Abrams is one of my favorite creators on television, but it’s apparent with work like this that he’s got the talent to succeed anywhere he chooses.
#25. On the Waterfront (1954)
The birth of the first real movie star, just as Citizen Kane introduced Orson Welles as the first real filmmaker, Marlon Brando bursts onto the screen. This isn’t his first or even first famous movie, but it’s still his greatest achievement, the one performance that everyone judged all his other performances on. That this is his first starring role to be featured on the list is not an indication that I experienced the same critical pitfall as just about everyone else, merely that in this instance, all the elements were given the chance to align at the same time.