Annie Hall

Alvy Singer and Annie Hall share a quiet moment in Annie Hall (1977)

“‘I would never want to belong to any club that would have someone like me for a member.’ That’s the key joke of my adult life, in terms of my relationships with women.”

Clever movies are a bit of a dying art. Nowadays, studios keep things pretty simple so nothing flies over the heads of their audience. Annie Hall, written and directed by Woody Allen (Crimes and Misdemeanors, Manhattan) and starring Woody Allen and Diane Keaton, is a film that’s clever to a fault. Some have said this is the greatest romantic comedy of all time, but I disagree—it’s not perfect, but that’s kind of the point Allen is trying to make. Much like the lead character Alvy, the film is smart and funny, but can be a bit condescending and has trouble connecting with people. This film was somewhat autobiographical for Allen, but he doesn’t romanticize his quirks and neuroses—he shows how they can be endearing, but also how they can be destructive. Overall, the film is intelligent, witty, and surprisingly deep in some spots, filling an odd void in the cinema world: admitting that it’s possible to be too smart for your own good.

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Eternal Sunshine of the Spotless Mind

Eternal Sunshine of the Spotless Mind

“What a loss to spend that much time with someone, only to find out that she’s a stranger.”

The manic-pixie dream girl is a common trope that pops up in a lot of movies. You know the ones, where there’s a guy who takes life too seriously and he meets this girl who’s wild and free and teaches him to have a new appreciation for life. Think Penny Lane in Almost Famous, or Holly Golightly in Breakfast at Tiffany’s, or Zooey Deschanel’s character in any movie she’s in. We always see the beginnings of the relationship and the transformation. But we never see how that plays out. We rarely see that while manic-pixie dream girls can be amazing, they can also be high maintenance, and it takes serious work to keep up the amazing aspects of the relationship—work that not every guy is willing to put in.

Eternal Sunshine of the Spotless Mind fills that gap by showing us a manic-pixie dream girl relationship after it has failed. Directed by Michel Gondry (The Science of Sleep, Be Kind Rewind) and starring Jim Carrey and Kate Winslet, this film offers a fresh look at what a romantic relationship really means and what it takes to make one work for imperfect people. It maintains a lot of that quirkiness from the other movies, but this one is layered with some heavy bittersweet moments as well. At times funny, at times sad, this is a great film about the ups and downs of love that doesn’t try to water down what makes relationships difficult, but still captures what makes them meaningful.

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The Apartment

The Apartment

“Ya know, I used to live like Robinson Crusoe—I mean, shipwrecked among 8 million people. And then one day I saw a footprint in the sand, and there you were.”

Many films that have tried to seamlessly blend tragedy and comedy together. This took off in the 90s and is still going strong today with films like Life is Beautiful, The Royal Tenenbaums, and Sideways. But in 1960, long before this was popular, The Apartment pulled it off beautifully. Directed by Billy Wilder (Some Like it Hot, Sunset Boulevard) and starring Jack Lemmon and Shirley MacLaine, this film is at times funny and silly and at other times dark and depressing, and the change is never jolting. It also deals with depression in a way that’s way ahead of its time. I had never seen this film before today, and it’s now one of my favorite classic films. If you like a little darkness with your comedy, this might be the perfect classic film for you.

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Gone with the Wind

Gone with the Wind

“If I said I was madly in love with you, you’d know I was lying.”

Gone with the Wind is a film that almost needs no introduction. Directed by Victor Fleming (The Wizard of Oz), who took over after George Cukor (My Fair Lady, The Philadelphia Story) was let go, this four-hour epic is widely heralded as one of the best films of all time, and, when adjusted by inflation, it’s the highest-grossing film of all time by a very wide margin—over seven billion dollars in 2018’s money. But I’ll be honest: I didn’t really understand much about it until I watched it today. I’d heard it was a romance, but that’s only partly true; it’s also about the disintegration of the old South and its culture in the aftermath of the American Civil War. And it’s told from the perspective of the Confederacy, showing an interesting, if somewhat misleading, perspective. The idea of a four-hour romance movie initially didn’t interest me, but this film is every bit as epic as it is romantic—which is to say a lot. The scope is grand, the characters are deep, and the conflict is much bigger than one relationship. I’m a little late coming to the party of reviewing this film, but I think this still holds up pretty well today. It really is that good.

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Moonrise Kingdom

Moonrise Kingdom

“I love you, but you don’t know what you’re talking about.”

Do you remember the first time you fell in love? That’s the feeling Wes Anderson tried to recreate with Moonrise Kingdom. It’s a story that focuses primarily on two kids—a rarity for Anderson. Even his children’s movie, Fantastic Mr. Fox, focused on the father of the family. The closest he’s come to this before was with Rushmore, which focused on a high school student. Moonrise Kingdom focuses on a pair of 13-year-olds, and it is, appropriately, filled with a sense of wonder and innocence that’s missing in most of his movies, which are more about disenfranchised adults who have trouble with relationships. Those adults are still here, but they’re in the background. The real story is in how these kids come together, although the relationships the adults have serve as a terrific foil for this. I wouldn’t say this is Anderson’s best film, but it’s probably his sweetest and most wholesome, and it absolutely deserves some attention.

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Your Name

Your Name

“The dream I must have had, I can never recall. But… the sensation that I’ve lost something lingers for a long time after I wake up.”

I’ve said it before, but I’ll say it again: I’m typically not a fan of anime, just like I’m typically not a fan of horror movies. But some movies, like Psycho and The Shining, are so good that they rose above the trappings of the horror genre. Your Name is a movie that rises way, way above the trappings of your typical anime. Directed by Makoto Shinkai (The Place Promised in our Early Days, 5 Centimeters per Second), this is the only anime movie to out-gross Spirited Away, which was a classic I’ve reviewed before. It’s one of the best love stories I think I’ve ever seen. There is a touch of the supernatural in this, but rather than that being the focus, it serves to enhance the drama and romance in the film that remain the focal point. This is a beautiful story beautifully told, and the fact that it’s an anime actually makes it better—that format tells the story better than any other would. Anime skeptics take heart: you will probably like this film.

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Breakfast at Tiffany’s

Breakfast at Tiffany's

“It’s better to look at the sky than live there. Such an empty place; so vague. Just a country where the thunder goes and things disappear.”

Have you ever seen something that seemed to say one thing at first glance, but upon further inspection actually says the exact opposite? I think Breakfast at Tiffany’s fits that pattern. Directed by Blake Edwards (The Party, The Pink Panther) and starring Audrey Hepburn and George Peppard, this film is often lifted up as a fun example of 60s style and culture—particularly Hepburn’s character Holly Golightly. But dig a little deeper and there’s a darkness just underneath the surface that takes a hard look at the cultural revolution of the 60s—why it existed and where it was going. This is fun to watch whether you understand the cultural context or not, but understanding it opens up a whole new plane of understanding for the film.

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Secretary

Secretary

“Who’s to say that love needs to be soft and gentle?”

BDSM used to be a pretty taboo topic—until the godawful Fifty Shades of Grey exploited it as an artless debacle. But back in 2002, it was a pretty foreign topic in cinema, often used as a raunchy joke if it appeared at all. Secretary, directed by Steven Shainberg (Rupture, Hit Me) and starring Maggie Gyllenhaal and James Spader, could have been either a sermonizing condemnation of the subject matter or a gratuitous exploitation of it; but the way the movie respects the relationship it portrays elevates this from the drivel that usually surrounds the topic. And with great writing and great performances from both leads, this is a fascinating portrait of how a real relationship with BDSM aspects could develop.

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Roman Holiday

Roman Holiday

“Rome! By all means, Rome. I will cherish my visit here in memory as long as I live.”

Though there are a lot of great older movies, the term “classic film” evokes some very specific feelings. Classic films show characters dealing with complicated and timeless emotions and situations. They’re fun and memorable without being overly sentimental. They transport you to another world that may or may not be based on reality, but is nonetheless fantastic. They have a sense of class and elegance that’s just missing in today’s movies. In my opinion, no movie is more classic than Roman Holiday. Directed by William Wyler (Ben Hur, The Best Years of our Lives) and starring Gregory Peck and, for her first major movie ever, Audrey Hepburn, this is a movie that, for me, is the quintessential classic film and will always be one of my favorites.

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The African Queen

The African Queen

“Nature, Mr. Allnut, is what we are put on this earth to rise above.”

In the classic era of cinema, female characters had an interesting but disappointing trait: they relied on the male characters to move the plot along. Though there were some strong female characters in the 30s and 40s, they were usually portrayed as less capable than the males, and the plot usually didn’t go anywhere until the males got involved. In most movies of that era, the females were also very dependent on the males. (I know there will undoubtedly be some exceptions, but this was the norm.) This era started to die off in the 50s (although traces of it can still be seen today), and for that, we owe a huge debt of gratitude to the 1951 movie The African Queen. Directed by John Huston (The Maltese Falcon, The Treasure of the Sierra Madre) and starring Katherine Hepburn and Humphrey Bogart, this is a movie that not only defined the romantic adventure genre (Romancing the Stone and Pirates of the Caribbean are modern derivatives), but it also showed that a female lead who is in every way her male co-star’s equal can make for a successful film.

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