The 100 Greatest Films Of All Time: A Wednesday Listicle (#100-91)

I promised that, coming fresh off of awards season, when Hollywood works itself into a lull, I would entertain you all with something special. Today, I present to you a labor of love twenty years in the making, and several thousand hours dedicated to film when they could have otherwise been spent socializing. Allow me to officially announce the start of a ten-week essay series: The Top 100 Greatest Movies Ever Made.

Finally, the thousands of films I have seen in my life will be put to use as I break down the best films ever made. Similar to the lists created by Time, Empire, Sight and Sound, and especially AFI, I have determined, using science, a list of the 100 greatest films in all of history. However, unlike AFI, or even Sight and Sound, this list will not be based on any specific country or region. Furthermore, this list will be a compilation of several different factors. Yes, I will be looking for the greatest artistic achievements, but that’s not all I will be crediting. I will also be looking at the impact each film has had over the years, as well as its popularity. So, for example, some animated or pop culture staples that normally don’t receive recognition could be popping up on this list (examples can be seen below). Meanwhile, acclaimed films like, oh, I don’t know, Citizen Kane, that have formed a monopoly in most lists’ number one slot may appear on this list, but I can promise you that they will not be first. This Top Ten will be original and honor the best films that often go overlooked. It’s also worth acknowledging in advance that I haven’t seen every movie ever made, so there are several films that may shockingly not make this list. There’s always a chance that new films will make this list over time, but for the time being, they just remain to be seen.

In lieu of the usual Honorable Mentions that go in this spot, I will be saving those for the final piece nine weeks from today. So instead of holding you up from the good stuff, let’s get right into it. Here are The Greatest Films Ever Made, #100-91.

100. Brazil (1985)

Brazil is a cornucopia of wrong ideas. It’s too dark for a children’s film, but too slapstick-driven for the serious drama it passes itself off as. It wants to be a tale of combating the bureaucratic totalitarians, yet ends far too depressingly for the average audience member. And while it wants to be a huge blockbuster, it’s far too smart. However, all of these “wrong” decisions are exactly the reason why Brazil is so right. A satirical look at society through the minds of Tom Stoppard and especially Terry Gilliam, the latter of whom created the more surrealist sketches for Monty Python, the film follows everyman dreamer Sam, portrayed by Jonathan Pryce in an all-time great performance, who grows tired of his mundane life in the bureaucracy of his futuristic world. Inspired by his fantasy sequences and the multiple visits from “terrorist” Archibald Tuttle (Robert De Niro), Sam determines to escape his oppressive society and live the life of his dreams with his fantasy girl (Kim Griest) despite numerous obstacles, including his cosmetic surgery-obsessed mother (a disturbing Katherine Helmond) and two bumbling government employees, played by Bob Hoskins and Derrick O’Conner.

This is the type of film where the writing is sharp, but the filmmaking is sharper. From the leitmotif of the song “Brazil” to the scenic design of a not-too-distant future, Brazil explores its society carefully and creatively. Inspired by films like Metropolis and literature like 1984, the film carefully crafts a world where the people are vain, consumerism is king, and the bureaucrats rule all. As lensed by Gilliam’s keen eye, we get to witness all of this in its hysterically dark glory. The film builds in insanity until its dark conclusion, but that doesn’t stop it from being a joy up to-and even including-that point. A scathing satire, laugh-out-loud comedy, and tragic cautionary tale all rolled into one, Brazil is Gilliam’s crowning achievement, and one of cinema’s greatest experiments.

99. Fantastic Mr. Fox (2009)

Sure, Wes Anderson has made more mature films than Fantastic Mr. Fox, but few are as joyfully sweet and hysterical. Fantastic Mr. Fox combines two things that most people wouldn’t think of combining: the crisp dialogue and keen eye of Anderson and the bizarre mind of Mr. Roald Dahl. The result is one of the greatest children’s films ever made, let alone one of the greatest films, period. The stop motion world that Anderson has crafted is so crisp, so sharp, and so real, it’s hard to think of this world as anything but natural. Perhaps that’s because Anderson chose to record the dialogue in actual nature, and opted to use natural props to create their worlds (the trees are actually miniature trees, the grass consists of tiny blades of grass, etc.). It makes for one of the most shockingly beautiful works of animation in history, and it makes the film an artistic masterpiece.

Of course, the only reason a Dahl/Anderson film can work lies in the dialogue, as well as those delivering it, and luckily Anderson went all out to perfect this aspect. Combining family drama, the heist narrative, and the classic Anderson-ian wit, the audience witnesses a heartwarming and thoroughly entertaining story for parents and kids alike. Of course, it helps when you have a cast of this caliber reading the dialogue. George Clooney performs a spot-on spoof of his Danny Ocean role, to great comedic effect. Anderson regulars Bill Murray, Owen Wilson, and especially Jason Schwartzman give the ridiculous dialogue the right mixture of humor and pathos. Jarvis Cocker almost steals the movie as henchman Petey, who narrates the story through song, much to the chagrin of the villainous Mr. Bean (second Dumbledore Michael Gambon relishes in the opportunity to play the villain here). However, the best voice work in the movie has to belong to Mr. Fox’s partner-in-crime/life, Felicia, voiced deliciously by Meryl Streep. Streep lends both her theatrical training and whimsical joy to the role, making Felicia a joy to watch and to listen to. Her reading of the line, “If what I think is happening is happening…it better not be,” might be one of my favorite lines in all of film history. It’s a fantastic ensemble reading fantastic lines surrounded by fantastic mise-en-scéne…in short, Fantastic Mr. Fox is, well, fantastic.

98. M*A*S*H* (1970)

Satire is one of the hardest art forms to pull off. It requires a sharp script, skillful direction, and incredible foresight. Luckily for M*A*S*H*, Robert Altman possesses all of these qualities, allowing his satire of life as a drafted soldier to shine. Yes, the film possesses a powerful message about the absurdity of war, using the thinly-veiled cover of the Korean War to comment on the absurdities of Vietnam. Of course, it isn’t the war commentary that draws us in, but the amoral activities of the characters. We are reminded that the idea of killing each other over belief systems doesn’t matter in the long run when we can just as easily have fun. From football games to golfing trips to trysts with the mistresses, the doctors engage in various acts of bacchanal, making the most of their lots in life and, more often than not, saving others’ lives.

The reason that Altman’s film works so well is that he knows exactly how to introduce us to the massive ensemble. By allowing us to see things through the eyes of talented Dadaists Hawkeye, Duke, and Trapper John (who would be unlikeable if they weren’t such damned fine doctors), we are allowed to see otherwise-stuffy characters and locations with a sense of wit and joy. From the lenient Captain Blake to Major Burns, from the caring Father Mulcahy to the nervous Radar, and especially the Oscar-nominated Margaret Houlihan (“Kiss my hot lips!”), the ensemble is filled with goofy, likeable characters that you want to watch in their series of shenanigans, which I’m sure inspired the television show of the same name. The movie might not be as well-remembered as the television show (which I consider a fine follow-up that is nowhere near as remarkable as the movie), but considering it was not only a box-office smash, but is still considered the high-water mark for satirical writing, I’d say this film stands tall in the field of great movies.

97. Amadeus (1984)

Sometimes just two parts of a film are so good, you can’t remember much else about them. That’s the case with Miloš Forman’s Amadeus, a film that is such a masterpiece in terms of writing and acting; you barely remember that the score, scenery, costumes, and direction are just as remarkable. A fictionalized account of the relationship between Antonio Salieri and Wolfgang Amadeus Mozart, the film is instead a study of art, jealousy, doubt, and all of the rest of those nasty habits that infuse the creative world. It’s a story about the jealousy those who work their asses off to be a moderately talented artist feel for those born with the gift, especially when said person doesn’t take their gift seriously. This struggle is perfectly embodied by the hard working Salieri, played in eloquent perfection by F. Murray Abraham, and the naturally gifted but emotionally stunted Tom Hulce.

Each piece of dialogue flows articulately from one scene to the next, with an abundance of memorable lines, a rarity for period films: “You go too fast!” “I absolve you!” “The duo becomes a trio, the trio becomes a quartet…” and The Masterpiece Monologue all stand out as classic pieces of dialogue, recognizable in every single film and show that spoofs them. Of course Abraham is the heart of this movie, standing tall as the bitter Salieri, but let’s not forget about Hulce. The uncorked energy, the braying laugh, and the genius behind his eyes all speak to the caliber of performance he is working with. These are two performances that absolutely shine, and the filmmaking behind them helps illuminate their work even more. The writing of Requiem near the end of the film is a near perfect sequence, filled with fire, passion, and urgency, beckoned onwards by the script, music, actors and editing all working together in unison. Amadeus may be one of the greatest films to come out of the 80s, and one of the greatest films to come out, period.

96. Pan’s Labyrinth (2006)

The Spanish have always had much more success with the magical realism genre than the Americans or Brits have. They seem to have an understanding of using fantasy and science fiction to explore political, social, and emotional issues that plague society. They have recently set a high water mark for the genre in Guillermo del Toro’s Pan’s Labyrinth (El Laberinto del Fauno). The film takes place in 1944, as young Ofelia (Ivana Baquero) is told by a Faun that she may be the reincarnation of a fairy princess, and must prove herself worthy of reentering the kingdom. All of this plays out as she begins life with her new stepfather, a captain in Franco’s army, who is determined to torture and execute every last Republican Rebel in the country. It is in this plot description that the film finds its “masterpiece” mantle, as the symbolic connotations of the plot elevate what could otherwise be a simple children’s fairy tale. Del Toro uses his filmmaking prowess, from storytelling to cinematography to art direction, to explore one of the most atrocious times in Spanish history. It explores the nature of innocence and evil, greed and human decency, and the complexities of life. The inclusion of the more fantastical moments serve as metaphors for the horrors of Ofelia’s childhood, his childhood, and the childhoods of several thousand Spanish children born under Franco’s regime.

However, just because the film uses fantasy as a metaphor doesn’t make the fantasy any less impressive. The design of this world is absolutely stunning to look at, from the gothic look of the set to the dark woods of the real world, from the stunning appearance of the Faun to the Hall of the Pale Man, each frame is a stunning painting, creating a haunting parable to frighten its viewer. The Pale Man sequence is a perfect example of mixing art direction, setting, makeup, visual effects, and dramatic tension to scare the living sh*t out of the viewer. It’s one of the greatest fantasy movies ever made, and when combined with its weightier material, it makes for one of the greatest movies of all time.

95. Swing Time (1936)

Sometimes these films aren’t very spectacular overall, they’re just really good at one particular thing. Thus is the case with Swing Time, a film with a fairly simple premise and the general acting and filmmaking of a Ginger Rogers and Fred Astaire film, but with impeccable dancing that changes what the art form means when placed into cinema. While dancing has been a form of expression since long before film existed, and has been a part of the silver screen since the very beginning, dance has really only been used as a form of expression, a way of showing us the characters’ psyches. It is rarely used as an interactive part of the story. Not so with Swing Time, perhaps the most innovative of the “Fred and Ginger” movies. Yes, every sequence is a lavish extravaganza of phenomenal dancing, but they also serve as a part of the plot, whether literally, metaphorically, or both.

Honestly, this film can be understood as a classic by breaking down each of the dance sequences. “Pick Yourself Up” is one of the greatest dance scenes in film history, with the slow build of “terrible” dancing by Astaire slowly building into an astonishing duet. “The Way You Look Tonight” may not be my favorite romance song from their repertoire, but it’s still a good one. “Bojangles of Harlem” may be problematic due to the use of blackface, but there’s no denying the artistic achievement found in the Shadow Dancing. However, nothing compares to the use of storytelling in “Never Gonna Dance.” The “Never Gonna Dance” sequence is such a remarkable use of storytelling through song and dance that it could, in many ways, be seen as a grandfather or inspiration for the famous La La Land finale. As for the performances, Fred may not be the most talented actor or singer, but his charisma will convince you otherwise, and his dancing will seal the deal. Meanwhile, Ginger continues to prove why the expression “She did everything he did backwards and in heels” exists, serving as the perfect match for Fred, verbally and physically. In the end, it all comes together to show that sometimes movies are masterpieces through the skilled demonstration of their stars’ talents, and nothing flashy is needed.

94. Almost Famous (2000)

Well-written ensemble flicks are sort of my bread and butter. Watching huge, sprawling sagas play out with great dialogue and hundreds of lovable characters is just an absolute joy. And few films of the genre have been quite as enjoyable as Almost Famous. Cameron Crowe’s ode to art as told through the combined crafts of writing and acting. Almost Famous is an extravaganza of the reasons the 70s gave us a cultural boon: the music, the critics, the fashion, and the lifestyle, all rolled into one. It’s funny, it’s sweet, it’s depressing, and it’s hopeful, all rolled into one. It captures an era where society had nothing going for them in their personal, professional, or political lives, so they had to turn to the art world to save them. It was an era that gave us Zeppelin, and Simon and Garfunkel, and The Stooges, and Black Sabbath, and Yes, and so many more all-time greats that I can’t even count them. It was a time where any fight amongst friends could be solved by singing along to “Tiny Dancer.” It’s the type of story that feels so real that it won’t surprise you at all to learn that it is semi-autobiographical to Crowe’s life, to the point you can forgive any clichés that pop up, because real life is a cliché. Crowe perfectly creates a tapestry of a singular time and place, a time we can look back on nostalgically, but would not and should not ever return to.

Of course, great ideas and great dialogue are nothing without a great cast backing it up, and luckily, Crowe knows how to pick it. Forget all the modern day stars who are now famous that pop up in first-time cameos, including Zooey Deschanel, Rainn Wilson, Jimmy Fallon, Michael Angarano, Jay Baruchel, Eric Stonestreet, and Nick Swardson. And I’m not even counting the minor roles for Anna Paquin, Bijou Phillips, and Fairuza Balk. I’m focused solely on the leads this film gives us. Patrick Fugit is an excellent audience surrogate as young William, the 15 year old high school graduate who goes on tour for Rolling Stone to write about rock band Stillwater (arguably the greatest movie band of all time), and he plays perfectly off the band, which consists of Jason Lee, John Fedevich, Mark Kozelek, and “Golden God” guitarist Billy Crudup, who seves as the friend, devil, and mentor that every kid wants/needs/should never have in life. Frances McDormand takes the stereotypical “nervous mother” role and amps it up to eleven, while still adding enough tics and traits to make it her second-best performance ever. I don’t know any other actress who could find the heart and soul inside lines such as “My son has been kidnapped by rock stars!” Phillip Seymour Hoffman, my all-time favorite actor, shows up as music critic Lester Bangs, who delivers the film’s moral in one of Hoffman’s best-ever monologues, and also inspired me to become a critic in the first place: “Great art is about conflict and pain and guilt and longing and love disguised as sex, and sex disguised as love.” It’s such a great line, but ironically, while Hoffman says it best, it is another character that personifies it. Kate Hudson is the heart of this film, perfectly embodying the 70s. Hudson’s Penny Lane is the free spirit of hope, inspiration and love that fills us with nostalgia and wins our hearts, but she also demonstrates exactly why the 70s were so creative. Art comes from pain, and Penny Lane is the embodiment of it. Wanting what she can never have, idolizing that which will never fully accept her, and incapable of ever feeling “normal” again, Lane is the essence of a time when American had lost hope in decency, between Vietnam, Watergate, a crashed economy, and the weakening or destruction of everything they’d fought for in the 60s. Penny is the pain that launched the careers of these tortured artists, and Hudson and Crowe manage to work together to find this pain in a young woman. All around, this is a time where great writing and acting not only create art, they personify it.

93. The Social Network (2010)

Dialogue is a great tool for telling a story, but it can also be a sharp weapon to drive the point home. And no film demonstrates this technique quite like The Social Network. Sure, it may have been a hell of a shoot, thanks to Aaron Sorkin’s wordy dialogue and David Fincher’s grueling takes, but my God, do they come together in such a shockingly delicious way. It explores human relationships, greed, fame, friendship, pride, and ego, exploring the hubris inside all men as they strive for greatness. In essence, The Social Network is almost a modern day retelling of Citizen Kane, although this one has the guts to actually use the real names of the characters. It uses Mark Zuckerberg, Eduardo Saverin, Sean Parker, and the Winklevoss twins as stock figures in a Shakespearean tragedy: Zuckerberg is the tragic hero, Saverin the Banquo betrayed along the way, Parker the corrupting Iago, and the Winklevoss twins the Laertes in our hero’s way. And the dialogue itself is on par with the Bard himself-Aaron Sorkin outdid himself in the rapid-fire dialogue that permeates this film. Line upon line lands in such frequent succession you may not be able to figure out what they’re saying until a third or fourth watch, but that just speaks to the level of intellect you’re dealing with from these characters-so smart, their minds move faster than the average human’s. The words carry the weight of a thousand emotions, and have a specific, epic ring to them, even if they would sound dumb in any real-life context (“A million dollars isn’t cool. You know what’s cool? A billion dollars.”) This also allows for greater opportunities for actors to launch into epic monologues and soliloquies-the kinds that make up the greatest films cinema can offer. Lead actor Jesse Eisenberg takes two monologues in two separate courtroom scenes and works them like putty into pure masterworks, almost in the same way Kenneth Branagh interprets Shakespeare or John Gielgud interprets Oscar Wilde. If you’re looking for a film to teach you how to write dialogue, look no further.

However, the reason The Social Network stands out isn’t just its screenplay. It’s the entire production, managed by skilled perfectionist David Fincher. Fincher makes his cast and crew do take after take for all eternity, but it results in some of the greatest work cinema has to offer. Each frame works in complete unison to study its characters and show what their feeling. The camera lingers on the faces of the actors, capturing their emotions, while framing them so that their isolation is key. The palette is muted to demonstrate their loneliness at the top while the score (Trent Renznor and Atticus Ross created one of cinema’s all-time greats in this one) hums depressingly onward. It all adds up to a tale of loneliness, greed, corruption, fame, and betrayal in a way few films ever truly have. It also doesn’t hurt that Fincher is aided by a group of young, but talented actors all looking to do their best to prove themselves as powerhouse actors. As mentioned, Eisenberg is a true master of the game, portraying the real-life Zuckerberg as one part assh*le, one part genius, and one part enigma. He is incapable of understanding social queues, but is above everyone else in his prowess, creating a way to connect people around the globe while ironically incapable of connecting to anyone himself. Of course, no actor can truly be great without a foil, and Eisenberg has two talented ones to work off of. Well, three, considering Armie Hammer pulls double duty as the Winklevoss twins, a pair of egotistical one-percenters whose embarrassment at the hands of the antihero drives them towards a lawsuit. Hammer mixes pride, arrogance, and swagger to give the twins individually unique and complex personalities, and it makes the film better for it. However, the film shines when Eisenberg gets to play off of Andrew Garfield, who makes Eduardo Saverin likable, complex, shy, nerdy, and fiery, all at the same time. You cheer for his friendship with Mark and are destroyed when the two friends are torn apart by the end of the movie, and it’s all through Garfield and Eisenberg’s compelling ability to hold your attention. I could go on praising what was accomplished with this movie, but I’ll just leave it at this: just watch the opening scene of this movie, a breakup scene in a bar. If you can watch that scene and tell me that this movie isn’t the one to define the current generation, then you just don’t understand cinema.

92. The Assassination of Jesse James by the Coward Robert Ford (2007)

Cinema is supposed to consistently change the game. It’s supposed to be artistically intelligent, technically stunning, and entertainingly complex. And no film in the past twenty years has really accomplished that the way Andrew Dominik did with his 2007 film The Assassination of Jesse James by the Coward Robert Ford. An obnoxiously long title for an obnoxiously long movie, Jesse James creeps along at a snail’s pace, slowly building its world and its characters so that when something dramatic or exciting does happen, its weight is felt. The opening train robbery is one of the best scenes in modern cinema, and the execution of the titular character is truly shocking, and yet these action sequences that would be the centerpiece of almost any other film make up maybe ten minutes of a two hour and forty minute plot. You see, Dominik isn’t simply interested in an action-packed Western, or even a study of two men’s relationship. He wants to explore the whole shebang-the way people lived their lives, why we celebrate celebrity, why we honor criminals, and what it means to live. He’s grappling with the most complex themes known to the human mind, and he does so in such an intelligent, yet entertaining way. The film isn’t about an assassination as much as it’s about human relationships, jealousy, idolization, and celebrity, each playing out in their own time as it explores why we idolize famous people, and what happens when that idolization builds without payoff. Of course, it helps when it’s paired with some of the most artistic filmmaking of the 21st century.

Dominik is the auteur of his generation, creating an epic of austerity on par with Terrence Malick and Werner Herzog. It helps that he assembled an all-star team to create the mise-en-scene. Perhaps the most important team member is cinematographer Roger Deakins, one of the greatest cinematographers in history, who performed his best work creating the bleak world of this story. His picturesque camerawork resembles old photographs from a long-gone era, drained of life and color, to represent the dissolving myth that surrounds the era. It is simultaneously rich and depressing, which is perhaps the best way to sum up the film as a whole. An image of James walking through the fog with a lantern is single-handedly the most impressive shot of the 21st century, and inspired the official logo of this website. The images are accompanied by a world-class score by Nick Cave and Warren Ellis, creating a moody and depressing atmosphere that perfectly captures the images on hand. Of course, none of this works without the perfect people in the roles. The cast is filled with the oddest, yet most impressive collection of character actors around, from Sam Rockwell’s Charley Ford to Jeremy Renner’s bitter cousin to, um, James Carville as a corrupt politician (it’s a weird, yet somewhat believable sentence, I know). And, of course, there are the two eponymous antiheroes, Jesse and Bob. Jesse is portrayed as the original celebrity, with swagger and charm for days, which means no one could play this role the same way that Brad Pitt could. At the height of his fame in 2007, with the media hounding his private life relentlessly, it certainly became a case of art imitating life. Yet as good as Pitt is in a role that may have just been an ultra-violent self-portrait, the film belongs to Casey Affleck as Bob Ford. Bob is an enigma of a character, platonically in love with his hero Jesse while despising his fame and his temper, wanting to be him while also wanting to become more famous than him. It’s a curious character study that could literally be replaced with any assassin, from Mark Chapman to John Hinckley, Jr., but it may not have been as interesting a result. Affleck portrays Bob with the same sort of internal reflection that makes him a great actor and won him an Oscar this year, but make no mistake: he has never been better than he is in this film. I won’t lie, it’s a long film, and could have been a bigger hit had it been shortened. But that’s exactly how you know this is a great film: when you sit down and try to get to the brass tacks of cutting anything, you find it impossible. Everything in this film is essential, in a spectacular way that only applies to true masterpieces.

91. Drive (2011)

Sometimes a film doesn’t have to say anything intelligent. Sometimes it can just look cool, feel cool, and be cool, just for the fun of it. As acclaimed director Jean-Luc Godard once said, “In order to make a film, all you need is a girl and a gun.” This is especially the case with Drive, a 2011 neo-noir that has nothing deep or intelligent to say the way many other films on this list do, but chooses to change the game through taut storytelling, exciting visuals, a suave protagonist, a beautiful girl to thaw his heart, and a gun. Well, several guns. And knives. And hammers. And elevators. Look, this is a violent movie, you guys. And that’s ok. Drive gives us a combination of several filmic devices to win its audience over. The opening car chase through the streets of L.A. is a perfect example of tension, all before we meet our characters or the plot. After that, things begin to twist and turn as our hero tries to make sure everything works out well for the good-hearted and retribution comes for the wicked.

Ryan Gosling just oozes all sorts of Steve McQueen cool as the unnamed Driver who navigates the L.A. underworld, aglow in a gorgeous neon wash. He fights for the love of the sweet and charming Carey Mulligan as gangsters Albert Brooks and Ron Perlman pursue them for being too close to their criminal activities. Director Nicholas Winding Refn shoots the film with a cool sheen and a peaceful ambiance, so that when the tension builds up, it feels extra thick, before exploding in a moment of unadulterated violence. It’s a simple film: your heroes aren’t all-good, but they’re simplistically heroic. Meanwhile, the villains are thoroughly awful, with Brooks chewing through all sorts of scenery to give Bernie Rose a layer of menace. And that’s only what we see on the bare surface. This is one of the slickest, smoothest pieces of movie editing in existence, flowing from one action set piece to the next, taking interludes for romance and heart along the way. When mixed with absolutely stunning cinematography and production design, as well as a rich electronic score, it creates a near perfect viewing experience. As Gosling drives through sun soaked L.A., slowly serenaded by the synth masterpiece “A Real Hero,” you’ll find yourself welling up with the sheer emotion of everything, and it will make you understand the sheer power of filmmaking. This film is why cinema exists.


Thanks for reading! As the list goes up every week, you can find the full Top 100 here, and you can find the rest of the articles each week below.

100-91 | 90-81 | 80-71 | 70-61 | 60-51 | 50-41 | 40-31 | 30-21 | 20-11 | 10-1

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