For each movie in the top 100, I’ve written a question to answer. (It would get very, very boring for me to have to write some variation on “boy howdy, you’ll never believe how good this movie is” one hundred more times.) There’s no exact sentence or word count I’m holding myself to here, but this is also isn’t going to function as a rationale for why 88 is better than 89 is better than 90. We’ll just be poking into some movies that are, simply, the very best.

90) Mulholland Drive (2001), directed by David Lynch

So what part of this movie seems clearest to you?

I am so glad we have this question instead of like, what part of this movie seems least clear to you. The clearest part of this movie, as far as I’m concerned, is the scene where Rebekah Del Rio sings “Llorando,” the Spanish translation of Roy Orbison’s “Crying.” Or…maybe. Fifteen years earlier, Lynch had used Dean Stockwell, in noticeable makeup, lip syncing to Orbison’s “In Dreams.” In Mulholland Drive, we’re meant to believe that Del Rio is singing this song, and Lynch makes us believe it. He’s got her in close-up, her lips are moving and vibrating with music, and Naomi Watts and Laura Elena Harring are close to sobbing as they watch this performance. And then…she faints. The song keeps playing, the words are still sung, and the tears, strangely, persist in falling. The inherent falseness of the performance, the inauthenticity at the heart of it, the fabrication of deep personal failing: none of them detract from audience emotion. None of them detract from the honest feeling that two women, neither of whom are really anything like what they are in that moment, are breathing in and out with mucus and tearstains. Mulholland Drive is frequently given as a kind of upside-down Hollywood story, not least because of the Watts character’s designs on acting there, but it’s an upside-down Hollywood story because Lynch has placed the thesis of commercial filmmaking, perhaps all filmmaking, in his picture. There are other directors and other movies, a couple of which I hold in higher esteem than Mulholland Drive, which also put movies under a bright light and say, “Look, it’s all just made up!” No one has ever done a better job with this concept than Lynch, and why should anyone have done? Lynch, the patron saint of authentic and unironic feeling, has not gilded lilies but has arrayed them to all of their natural advantages.

89) The Palm Beach Story (1942), directed by Preston Sturges

Pick your poison: Sturges slapstick, Sturges dialogue, Sturges scenarios.

If we were talking about Unfaithfully Yours, it’d be the slapstick, and if we were talking about Christmas in July, it’d be the dialogue. But we’re talking about The Palm Beach Story, which starts and ends with some weirdness that even David Lynch would put a hand to his forehead in response to. Did you ever think your relationship with your spouse might be suffering because you might have accidentally married her twin who’s never let on after all these years? That’s the threat at the beginning of The Palm Beach Story, or maybe it’s a joke, or maybe it’s actually incredible frightening, but hey, it doesn’t seem to make any difference until the last scene when all of a sudden multiple twins turn into a way to give this comedy an ending so Shakespearean that they practically call in Hymen to do the honors. This is quippy, although my favorite character in this entire film is not one of the leads but Sig Arno’s Toto, who speaks in…zips? Magyar? what Martin Short was doing in Father of the Bride? In any event the wit of the dialogue is not what’s getting me. Somehow I haven’t even discussed the Quail and Ale guys who embody strangeness on a train, or the Wienie King. All I really want to say is that this movie is so funny and weird that it’s a little bit menacing, like when you watch a cat contort its body in a freaky way and run out of the room.

88) Singin’ in the Rain (1952), directed by Stanley Donen and Gene Kelly

This movie was released twenty-five years after the advent of the talkie, or, in other words, the distance between now and Titanic. Does this movie have perspective or is it just playing the hits for MGM?

There’s some perspective in Singin’ in the Rain, for sure. I mean, if you want to watch a movie that has no perspective at all about the transition between the silent and sound eras, The Artist is right there for the watching. (Hahaha what a terrible use of time that’d be!) When I saw The Barretts of Wimpole Street, a movie which has this absolutely oppressive blocking, you can watch it and pinpoint where the microphones are on the set based on where Norma Shearer and Charles Laughton are pointing their faces. For me, it’s why that scene where they try to figure out where Lina Lamont’s microphone should go is so funny. It’s not just a comedy of errors, but it makes me think of watching Fredric March practically bounce up and down in Barretts because he’s definitely not allowed to bounce side to side. On the other hand, this is definitely just playing the hits. When Gene Kelly sings “Lucky Star,” all I hear are the endless iterations of that song which populated MGM movies throughout the ’30s. If you want to hear basically any number from Singin’ in the Rain with Judy Garland involved, you can find it in 1939’s Babes in Arms; if you want to see Gene Kelly do “Make ‘Em Laugh,” watch The Pirate. There’s a fair bit of forced nostalgia baked into the crust of Singin’ in the Rain, a paean to Arthur Freed and Nacio Herb Brown which for audiences of the early ’50s would have reminded them of non-atomic times.

87) Mississippi Masala (1991), directed by Mira Nair

Come on, is this movie actually that hot or does it just have sex scenes.

There are these casual tracking shots in Mississippi Masala where the camera just follows Denzel Washington and Sarita Choudhury walking side by side, sometimes not even touching all that much, and the tension between those two is just almost unbearable. The actual sex scenes, which are not even that graphic, are about muscles tensing and relaxing, the contraction which you know is being met in a more sensitive place. A couple months ago I was listening to the This Has Oscar Buzz podcast do an episode about Wild Mountain Thyme, one of the Internet’s favorite confusing movies of the past few years, and one of the points they made has stuck with me. Jamie Dornan and Emily Blunt are far and away the two hottest people in town: shouldn’t they have just ended up with each other sooner? On a rational level, this obviously makes no sense, but in a movie there’s an expectation that two hot people in a world of like, less attractive people are supposed to glom together. Washington and Choudhury are both totally beautiful, so regardless of how much baggage Roshan Seth is carrying, they were absolutely made for each other. What makes this a really delicious romance is the way that the two of them complete each other. For Demetrius, Mina is the smart, passionate woman he has not been able to find anyone like in Greenwood. For Mina, Demetrius is goodness without slyness or resentment, pure confidence and competence. Even their best features complement each other. Washington’s got that ridiculously cocky grin, and Choudhury has enviably thick hair; one seems to almost point in the other’s direction. What really makes this movie steamy, at least for me, is that the sexiest scenes in this movie aren’t about Demetrius chasing Mina, but the two of them agreeing tacitly to terms where they have one another.

86) The Age of Innocence (1993), directed by Martin Scorsese

Does this movie have the best twist of the 1990s?

I don’t think it’s even close. Take any of your famously twisty ’90s films, from Fight Club to The Usual Suspects to Wild Things to The Sixth Sense, and all of them feel like they’re designed around that moment where the whole theater is supposed to go “Oh my godddd” together, the sound of hundreds of empty bags of popcorn falling on the sticky floor together and making a small, forgettable flapping noise in unison. The twist in The Age of Innocence is not that May knows that Newland’s been having the steamiest affair in recent Gotham memory with her cousin Ellen. It’s so obvious to everyone that even people in North Jersey knew about it and could pretend it made them sophisticated. The twist is that Newland never learned his wife’s quality. There’s that great scene where Ted accidentally reveals that May, quite frankly, played Newland like his motivations were sheet music, and it sends the old man reeling. What a remarkable twist it must be to believe through her death that one’s wife was proper and fine, only to learn after her demise that she was every bit as sophisticated and even conniving as the woman one pined after instead. It’s a hugely complicated emotional moment, a twist that squeezes the heart rather than manufacturing plot.

85) When Harry Met Sally… (1989), directed by Rob Reiner

What does it say about the film’s conception of romance that its most likely couple is between young Clemenza and Princess Leia?

The thesis of When Harry Met Sally is not exactly that men and women can’t be friends because of the looming aspirations to hanky-panky, but it’s not not that. I think everyone knows that the Harry/Sally relationship, one which is a deep personal friendship over the course of years and then survives an unplanned sexual encounter (barely!), is about as realistic a courtship strategy as letting an adolescent leopard loose in Connecticut and seducing your opposite number while looking for Baby. Shoot, the movie understands that. This very nearly ends with Harry and Sally not even friends anymore, and the raw dogging reality version of this picture absolutely does not send Harry running through the streets on New Year’s Eve to win her back. Jess and Marie meet in one of the more incestuous meet-cutes I can think of in a movie. (I’m imagining the missing scene in this movie where Harry’s like, “Say, Sally, have you thought about how much more complicated our sublimated sexual desires for one another would be if we made it so your best friend had banged me and my best friend had stirred your yogurt?” and Sally’s like, “Harry, that’s disgusting [has brainwave inside perm], but maybe you have a point.”) Mercifully, Jess and Marie, introduced by friends, have that serendipitous moment with one another. Marie has read something Jess has written, not knowing it’s his, and what he’s written has left an imprint in her mind; Jess, who Kirby brings some vulnerability to, obviously thrills to the fact that she likes something about him already. There’s a reason our world loves stories of accidents or fates deciding romance, even if those romances are star-crossed; it’s the only explanation we have as to why people can fall in love when there ought to be a hundred Berlin Walls’ worth of obstacles for even a fling. But Jess and Marie click. It’s not their movie, but the movie seems to believe most in the possibility of their love.

84) Metropolitan (1990), directed by Whit Stillman

Given some of the slightly amateurish touches in some of the acting, Stillman’s direction, etc., is it fair to say that this is the “most valuable” screenplay in American movie history?

One of my hobbyhorses is about the value of a screenplay. The list of really showy screenplays which have built great movies is a short one indeed. Casablanca is probably the most quotable movie in American history for the sheer number of iconic lines it holds, but every one of those lines makes sense as something that Rick or Ilsa or Renault would say in that moment. The words are like a sprig of spearmint as opposed to a full tube of toothpaste splooging gooey on a plate. (A Few Good Men is probably America’s most toothpaste movie, though as a kind of self-preservation I don’t think about this topic much.) Whit Stillman is not immune to the toothpaste experience, certainly; The Last Days of Disco comes with some real tartar control. But Metropolitan, a delightfully quotable picture, is also about basically inhuman college kids reveling in their stifling social circles. Chris Eigeman makes me laugh the hardest in this movie, but Taylor Nichols must be the most essential person on screen. I always forget how early the line “You’re a Fourierist?” comes, but it’s such a wonderful statement of intent for this movie about these class-conscious people who have no small amount of education but whose emotional urbanity cannot match their ability to dress up pretty. The idea of the UHB is memorable, perhaps even pithy to a fault, but of course Charlie would need to create terminology for people like himself. It’s the way people whose values are based not on cash but on wealth can cement themselves as tangible beings; even at the risk of pathology, there needs to be terminology.

83) Daughters of the Dust (1991), directed by Julie Dash

Does the steadiness of this film make it more or less dreamlike?

I think the best way to answer this question is to say that this is about as Faulknerian a film as has ever been made, although it of course has thoughts and insights that even Faulkner at his most perspicacious never quite made. I’ve seen this one a couple times now and both times I have been amazed at how easily this picture vaporizes time. It’s not that long, less than two hours, and yet the experience of watching it is not easily measured in minutes or seconds. The images occur just a little too slowly, the movement of cloth or boats or fronds slightly off. The overwhelming memory of this film is one of white clothes, especially beautiful white dresses, on tawny sands, moving without haste, perhaps even still. But of course that’s not at all what actually happens in this movie. Eli beats his breast and struggles verbally and physically with the child he’s not sure will be his. On the other hand, people eat on the beach in a group, creating a wave of small movements that deny the stillness of other segments of the film. I can’t think of another movie that quite understands the warmth and languor of beachlight in the way that Daughters of the Dust does, the way that it in the late afternoon and early evening it coats everything it touches.

82) Pilgrimage (1933), directed by John Ford

So why exactly are you a sucker for Ford’s F.W. Murnau hero-worship?

Scott Eyman’s Print the Legend: The Life and Times of John Ford is a very strong biography, and perhaps just as importantly a wonderful read. Eyman hypothesizes that Ford, who made dozens of silent movies before he became like, John Ford, was responding to two directors as he was developing his style. The first was D.W. Griffith, from whom Ford borrowed an occasionally celeritous camera and an ability to layer even a still frame with deep, three-dimensional, even undulating movement. The second was F.W. Murnau, whose facility with shadow and spiritual feeling remains unmatched. There’s probably no film that Eyman watched for his Ford biography that he spends more time piling on than The Fugitive, an extremely Murnau interpretation of The Power and the Glory. Clearly, having rated The Fugitive 170th in an earlier post, above Jaws, Imitation of Life, and T2, I don’t have the same problem that Eyman does with that picture, or without Ford’s adulation of Murnau. Pilgrimage is, as I’ve written previously, a film which uses three individual shots to direct the entire film. Each one is a response to the other, each one essential to highlighting what Ford intends to highlight, and it’s this attention to detail, the shot-by-shot manual that Ford, like Bong Joon-ho, can keep in his head. The beauty of this film is pure Murnau, though the plot—a domineering mother signs her son up for World War I, where he’s killed, and then freaks out about seeing his grave—has much of the social register of a Griffith movie.

81) Superstar: The Karen Carpenter Story (1988), directed by Todd Haynes

Can a Barbie doll give a great performance?

The wryest answer to this question is: “It depends on whose hands she’s in.” Actresses from Millicent Simmonds to Cate Blanchett to Julianne Moore have been just spectacular in Haynes pictures; if we’re being honest, it’s easier for me to rattle off great performances by women in his films than it is for me to rattle off great performances by men. The Karen doll is, in the most unusual way, part of that lineage. In his best films, Haynes helps us to love the leads, willing to let us see the defects in their character but also certain that those people can be loved regardless. The diabolical cleverness in this film can be jawdropping in its audacity, never less than when Haynes sets up the pleasure of self-denial in an eating disorder to the sound of The Carpenters’ cheerful “Top of the World.” But for as unhip as she is, there’s never a doubt for Haynes, or for us, that Karen Carpenter deserves anything less than our adoration. Over the course of the film, the Karen doll is hollowed out, thinned, hurt, and we have to feel for that doll, feel the person who the film opines was actively controlled and mistreated by her family in pursuit of financial security. Something I’ve always been really moved by is that Haynes, intent on this story, does not bring in an actress who would have to lose weight and mangle her own body to play Karen. He finds an alternative, and in his humanist way finds a striking, pitiable alternative.