My top 25 movies of all time

Not Greek mythology, but still mythology

What’s going on here? Best of? What motivated that?

Well, the New York Times recently published a list of its 100 top movies of the 21st century (seems a little premature, as we’re only 25 years into the century, but okay).

Then Greg Gioia of Substack wrote his top 100 movies of the 21st century, and I thought he did a bang-up job.

Being a fossil, I almost never watch feature-length movies anymore, and when I do, lately, it has been film noir stuff from the 40’s and 50’s (check out Thieves’ Highway, directed by the great Jules Dassin). I am definitely not a child of 21st century cinema.

And yet, inspired by the NYT and Greg Gioia, I offer here for your summer enjoyment my 25 favorite movies of all time, be they from the 20th or 21st centuries.

Some notes first

My opinion is that the Golden Age of American cinema happened between 1946-1963, and a second, excellent age came between 1986-1996. But there are a couple of good ones from the 21st century, yes indeed.

You’ll notice there are plenty of the best of all time according to others left out of this list. That’s because my top 25 is mostly about movies I don’t mind watching over and over again, and where I find new things to appreciate every time. In the era of streaming, if I can watch a movie all the way through without fast-forwarding, that’s a really good movie.

For example, I agree that The Shawshank Redemption is in everyone’s top 10, but it’s not something I’ll watch over and over, while Glengarry Glen Ross (a film on no one’s top 25) I watch pretty much every six months.

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Here they are, title first in bold, director(s) in parentheses, followed by year of release.

#25. Tootsie (Sydney Pollack), 1982.

Such a feel-good fantasy. You have to like Dustin Hoffman as the cross-dressing, unlikely soap opera star, but I fell in love with his girlfriend Teri Garr. She has always been a favorite of mine since her turn in the original Star Trek as a guest star, but her intrinsic goofiness is just perfect for this utterly goofy, heart-warming comedy.

#24. Bull Durham (Ron Shelton), 1988.

Having lived in Durham, North Carolina, and having attended games at the ballpark where the movie was shot and having driven past the house that was used for Susan Sarandon’s home, and having gone to many Durham Bulls games just in general, there’s no way I can’t put this movie in my top 25. It’s also a pretty entertaining baseball movie.

#23. Toy Story 2 (John Lasseter), 1999.

The first Toy Story was pretty terrific, but this one ups the ante with an especially high-stakes premise that humanizes the toys in heartbreaking fashion. The best part of this movie is the song “When She Loved Me” by Sarah McLachlan.

#22. Big Night (Campbell Scott, Stanley Tucci), 1996.

Probably the best food movie I’ve ever seen, there’s no scene or moment here that isn’t memorable and beautiful. Stanley Tucci and restaurant partner Tony Shalhoub are trying to get their Italian eatery off the ground in 1960’s New Jersey with a whizbang opening, and they pin their hopes on hosting the music star Louis Prima and his band, who will presumably tout the restaurant afterward to his friends and audiences. What happens is not what you expect.

#21. Moonstruck (Norman Jewison), 1987.

Cher and Nicholas Cage chew the scenery while the supporting cast helps to create an effective antidote to the Italian mafia movie. This is Italy as it’s meant to be: furiously loving, unapologetically romantic and sentimental, hilarious, heart-warming, family-oriented, wacky, and full of truth.

#20. Dr. No, From Russia with Love, Goldfinger (first two Terence Young; third Guy Hamilton), 1962-1964. It’s somewhat cheating to put three movies into one slot, but they really do go together as a unit. Of these, my favorite is From Russia with Love because it holds together best as a spy movie, and the other two are somewhat ruined by their spectacular and unlikely endings. Cannot say enough about Bond girl Daniela Bianchi in From Russia with Love. And the title ballad sung by Matt Monro is one hundred percent singable.

Image found here.

#19. 2001: A Space Odyssey (Stanley Kubrick), 1968.

I saw this a few years after its release when I was nine or ten years old, and I was completely freaked out. I still get freaked out by it, but it is so mesmerizing all the way through that I can’t help but watch it over and over.

#18. The Big Lebowski (Joel Coen), 1998.

This is extremely wacky, offbeat, and strange, but it ends up being a highly complex L.A. private detective yarn. That’s the genius part.

#17. Glengarry Glen Ross (James Foley), 1992.

The David Mamet play about cold-calling real estate sales guys in New York City is famous for the scene where Alec Baldwin says it takes brass balls to sell real estate, but the ensemble performances of Al Pacino, Jack Lemmon, Alan Arkin, and Ed Harris are the real draw. Plus a top-notch jazz soundtrack.

#16. Rear Window (Alfred Hitchcock), 1962.

For this movie, all your really need to know is Grace Kelly. It’s pretty terrific in a lot of ways, but Grace Kelly is one hundred percent the reason it is a must-see.

#15. The Sting. (George Roy Hill), 1973.

Robert Redford and Paul Newman play the heck out of this con game flick. I adored this movie when it came out and it still holds up today. I watch the poker game scene between Newman and villain Robert Shaw on YouTube on the regular.

#14. The Trip (Michael Winterbottom), 2010.

This isn’t strictly a movie, but a kind of straining and concentrating of the best moments of a UK television show of the same name, starring UK celebrities Steve Coogan and Rob Brydon. Coogan, playing a version of himself, asks Brydon, also playing a version of himself, to go on a tour of restaurants and sights in the north of England, ostensibly for Coogan to write a magazine article. Their relationship, bits, jokes, insights, flaws, and talents are all on prominent and highly entertaining display.

Coogan left, Brydon right. Image found here.

#13. Thelma and Louise (Ridley Scott), 1991.

I once published a scholarly article about how this movie is a reverse Odyssey, redone for the Penelopes that decided to leave home instead of waiting for their peripatetic men. It was boldly feminist for the year 1991, but it is also extremely entertaining, perfectly shot, and the relationship between Susan Sarandon and Geena Davis is the deserved centerpiece. Brad Pitt does his best work here. He never had a better role.

#12. Sideways (Alexander Payne), 2004.

The stereotype is that every story is really about a writer, regardless of what occupation the main character has. This movie is actually about a writer (Paul Giamatti), his actor friend (Thomas Haden Church) and the sad, ugly, poignant, hilarious, hopeful, wistful, and tragic realities of various types of addiction. Beautiful soundtrack, beautiful performances by Sandra Oh and Virginia Madsen. Beautiful movie.

#11. The Matrix (Lana and Lilly Wachowski), 1999.

Back in the old days when I was beginning to teach high school, someone said to me, “You need to watch The Matrix if you want to understand kids today.” It was true. They all were obsessed with it, and rightly so. I never much liked the sequels. This movie stands on its own as one of the best American stories ever told.

#10 O Brother Where Art Thou (Joel and Ethan Coen), 2000.

This was the first movie I ever saw on DVD, and I thrilled at the sepia tones of Mississippi as I laughed out loud through the entire thing. Is this an updating of the Odyssey? No, it’s really a send-up of it, and a terrific one at that. George Clooney and his buds are national treasures in my book.

#9. Blade Runner (Ridley Scott), 1982.

I’ll never stop watching this movie, despite the fact that I really do not like violence in movies and most of the movie is a process of hunt-and-kill. I admire the world-building, the attention to detail, Harrison Ford’s film noir hero sensibility, the beautiful way the is-an-android-a-human trope is handled, and of course, Sean Young’s bee-stung lips.

Image found here.

#8. Rain Man (Barry Levinson), 1988.

I watch this movie at least once a year if possible, depending on where it comes up in my life. I know Tom Cruise is not one of the most beloved actors of all time, but his performance in this one really captures the depth of a young man who had a deeply wounding relationship with his father. Dustin Hoffman, of course, does a great job, and there are multiple scenes in this one that are pure crystal. I think the final interview with director Levinson playing the role of the psychologist, tapping his pencil on his desk, is the very best one. But that’s just me.

#7. Breakfast at Tiffany’s (Blake Edwards), 1961.

This is an iconic choice, but for me the hook is in the perfectly-rendered relationship between a writer who is an emotionally-needy rescuer and a damaged woman with borderline personality disorder. Audrey Hepburn of course is an absolute gem, and her “Moon River” scene is utter heaven, but the real power of this movie is in the non-happy ending, which you can see is non-happy if you have any emotional or psychological depth at all. Devastating.

#6. The Natural (Barry Levinson), 1984.

A number of people will say that this is too corny, too mythologically American for them, but I say, bring it on. Baseball is that one American activity that lends itself at the DNA level to mythology. Everyone gives the most fantastic performances in this one. I’m a sucker for the baseball-shatters-the-light-standard-and-keeps-going scene, but the best one is where Roy strikes out the Whammer on three pitched balls. Nothing better.

Image of Roy Hobbs’s bat found here.

#5. The Princess Bride (Rob Reiner), 1987.

As you wish.

Image found here.

#4. Vertigo (Alfred Hitchcock), 1958.

I grew up in San Francisco, and I have to admit that what some people would consider the most boring part of this movie, when Jimmy Stewart is tailing Kim Novak through the streets of San Francisco, is one of my favorite parts. Yeah, I know that corner of Clay and Taylor. Yeah, I know that neighborhood near Coit Tower. Yeah, I know the Museum at the Legion of Honor. Yeah, I know Fort Point and Crissy Field.

But I love this movie because I never saw the twists coming. Never in a million years.

#3. When Harry Met Sally and Sleepless in Seattle (Rob Reiner, Nora Ephron), 1989, 1993.

These two go together even though they really deserve to be choices on their own. Both are terrific in different ways, but if I had to pick, it would be Harry at 3A and Sleepless 3B. Harry has the most overall memorable moments, but Sleepless has the best dénouement. The Empire State Building indeed.

#2. School of Rock (Richard Linklater), 2003.

As a schoolteacher…

I don't have to finish that sentence. If you’ve ever worked with the younger set, you will appreciate the beauty of Dewey Finn’s awakening as a motivator of young minds. It is so funny, and quotable, and inspirational, and beyond the pied-piper performance of Jack Black, you have to love Joan Cusack’s utterly wacky and perfect turn as “The Man.” Magic.

Image found here.

#1. Defending Your Life (Albert Brooks), 1991.

My number one is a movie I come back to over and over again as a touchstone for my own life and an antidote when I’m feeling down. Albert Brooks dies and goes to a limbo-like holding tank for the Universe, where humans defend their life choices in a court-like setting. If your life was ruled by fear, you are sent back to Earth reincarnated as someone else, but if you’ve overcome your fears, you get to “move forward” into a higher plane of existence. Brooks is hilarious and his romance with Meryl Streep will pluck at your heart-strings. Unusually poignant, stirring, laugh-out-loud funny, and truthful about what matters in life.

Just missed the cut (in no particular order):

Gladiator, Midnight Run, Napoleon Dynamite, One Flew Over the Cuckoo’s Nest, Back to the Future, Dumb and Dumber, Chinatown, The Freshman, Get Shorty.

Honorable mention (in no particular order):

Pirates of the Caribbean (first one), Casablanca, American Graffiti, Disney’s Hercules, Apocalypse Now, The Shawshank Redemption. Broadcast News, Annie Hall, Never on Sunday, The Bicycle Thief, Diner, Groundhog Day, Lost in Translation, The Lord of the Rings, The Godfather, Killer of Sheep, Top Gun (the original), Predator (the first one), Alien, Episodes 4-6 of Star Wars, The Truman Show, Memento, Donnie Darko, The Conversation, Three Days of the Condor, Ghostbusters (the first), Breaking Away. Henry V, Big, A League of Their Own.