Oh man!
I usually read your posts and really agree, but High Noon? Barry Lyndon? 
Ok, I’ll give you Barry Lyndon (a bit bloated, too much for even the most beautiful cinematography to counter), but High Noon just built and built… until… it was resolved!
Ok, I really liked it for the characters and acting.
Not until me and Harvey get the rules straightened out.
I thought it might be fun for someone to guess, so I’ll answer in a spoiler tag. It’s nothing super interesting by any means.
They’re all taken from the IMDB top 250 and sorted from least votes to most. I figured that a movie that cracks the top 250 with FAR fewer votes than the really well known ones, has a devoted following of sorts. The logic may not be mathematically sound, but it was just the first unique way I thought of to sort a long list of movies I’d like to check out sometime.
As for the subjectivity issue, this is a vetted list, that I’m further vetting on a board with a lot of people whose opinions I respect. It at least helps narrow down the field a bit. I’m informally tracking the results for each movie mentioned more than once so that I have a metric as well.
Ditto that.
I’ve seen about 90% of the films on that list.
All are good films though different tastes will say otherwise - there are a few I’m not particularly keen on. The top five that struck me as being accessible and entertaining to a newbie:
The Third Man (naturally), classic thriller that really hasn’t dated, fast-paced, funny, perfectly cast, killer ending.
High and Low: very good police procedural, directed by a master (Akira Kurosawa) and based on a novel by Ed McBain. Patience is required.
La Strada: heart-breaking drama from Federico Fellini.
Paths of Glory: anti-war film by Stanley Kubrick, another perfectly-cast film, moves very quickly, fantastic script, devastating and unforgettable.
High Noon: stellar, cynical, classic western.
Grave Of The Fireflies
Possibly the saddest movie in the world, no spoilers but it follows some young war orphans and pulls no punches.
Nihilistic.
I was able to identify it instantly, since I made a similar list at one point for a similar reason! (My list was restricted more by date, though – something like 1940-1985.)
My favourites:
The Best Years of Our Lives (1946)
Anatomy of a Murder (1959)
Nausicaä of the Valley of the Wind (1984)
The Wild Bunch (1969)
Touch of Evil (1958)
Mr. Smith Goes to Washington (1939)
The Treasure of the Sierra Madre (1948) <– probably my favourite from the whole list
The Manchurian Candidate (1962)
All About Eve (1950)
Roman Holiday (1953)
Manhattan (1979)
My Neighbor Totoro (1988)
Cool Hand Luke (1967)
Sunset Blvd. (1950)
Singin’ in the Rain (1952)
Butch Cassidy and the Sundance Kid (1969)
The Bridge on the River Kwai (1957)
Ben-Hur (1959)
Ones that I found underwhelming:
Kind Hearts and Coronets (1949)
The Night of the Hunter (1955)
The Celebration (1998)
Yojimbo (1961)
Bicycle Thieves (1948)
8½ (1963)
The Seventh Seal (1957)
Interesting way to come up with that list, dnooman. I might suggest swapping the Altman selection to either Nashville or The Player, swapping Kubrick’s selection with The Killing, including at least one Coen brothers film, and cherry pick a few more films from the '70’s.
From your list, these are the ones I especially like. I didn’t bother deciding if any are “bad”.
But – you’re missing a lot of great movies. 
.
Judgment at Nuremberg (1961)
The Best Years of Our Lives (1946)
Anatomy of a Murder (1959)
Witness for the Prosecution (1957)
The General (1926)
All Quiet on the Western Front (1930)
The Man Who Shot Liberty Valance (1962)
It Happened One Night (1934)
The 400 Blows (1959)
Yojimbo (1961)
The Wild Bunch (1969)*
Notorious (1946)
Bicycle Thieves (1948)
Touch of Evil (1958)*
The Manchurian Candidate (1962)*
Ran (1985)
High Noon (1952)
City Lights (1931)
All About Eve (1950)
Roman Holiday (1953)
Strangers on a Train (1951)
Network (1976)
The Apartment (1960)
Rashomon (1950)
M (1931)
A Separation (2011)
Metropolis (1927)
Paths of Glory (1957)
Cool Hand Luke (1967)*
The Third Man (1949)
The Maltese Falcon (1941)
Cinema Paradiso (1988)
For a Few Dollars More (1965)*
Gandhi (1982)
Butch Cassidy and the Sundance Kid (1969)*
I’ve seen the following:
Must See: Ran (1985)
Must See: Rashomon (1950)
Must See: Grave of the Fireflies (1988)
Fun: My Neighbor Totoro (1988)
Skippable: High and Low (1963)
Skippable: The Killing (1956)
Skippable: Nausicaä of the Valley of the Wind (1984)*
Skippable: Castle in the Sky (1986)
Skippable: Metropolis (1927)
Skippable: Paths of Glory (1957)
Skippable: For a Few Dollars More (1965)**
Tedious: Gandhi (1982)
Avoid: Barry Lyndon (1975)
:smack: Can’t believe that I missed The Killing earlier.
Gotta disagree with you, Sage Rat, on The Killing and on High and Low - they would both be must see’s for me, along with:
The Wages of Fear
Stalag 17
The Hustler
The Night of the Hunter
The Big Sleep
Yojimbo
Touch of Evil
The Treasure of the Sierra Madre
The Manchurian Candidate
All About Eve
Dial M for Murder
Rope
Strangers on a Train
Double Indemnity
Network
The Apartment
Rashomon
M
Cool Hand Luke
The Third Man
The Maltese Falcon
Cinema Paradiso
For a Few Dollars More
Sunset Blvd.
Butch Cassidy and the Sundance Kid
Thanks, but I had no part in choosing anything about this list other than the way it was sorted and listed. A handful of the ones listed here would be on my fave list, but my fave list would look quite different.
Yes, I know. This ended up being primarily a list of older movies that I hadn’t seen, and wanted advice on which ones to cherry pick first.
BTW, I haven’t put your picks into my spreadsheet yet, but I can already tell that you are the guy who is most likely to enjoy whatever classic a random Doper might choose. You must come to my M. Night Shyamalan film festival so that you can taste scorn for once. You’ve been hogging all the adoration for way too long buddy. 
So many of my favorites are already listed, but I would add these for sure:
The Music Box
Duck Soup
Manhattan Melodrama
Pygmalion
Casablanca
The Sea Hawk
49th Parallel
Gentleman’s Agreement
The Postman Only Rings Twice
Mildred Pierce
The Snake Pit
Destination: Tokyo
Thirty Seconds over Tokyo
The Purple Heart
Run Silent, Run Deep
This Is the Army
Yankee Doodle Dandy
Key Largo
Love Me Or Leave Me
The African Queen
The Spirit of St. Louis
Bad Day at Black Rock
The Seven-Year Itch
Some Like It Hot
Bus Stop
Funny Face
Never Steal Anything Small
Psycho
A Shot in the Dark
Experiment in Terror
The Magnificent Seven
The Great Escape
The Train
Wait until Dark
American Graffiti
Of these, I’ve seen the following:
Infernal Affairs (2002)
Ip Man (2008)
Cool Hand Luke (1967)*
Howl’s Moving Castle (2004)
I liked Infernal Affairs (The Departed is an inferior knock-off) and Ip Man (but if you’re not interested in martial arts, you might not be interested). I watched Cool Hand Luke more than a decade ago and can’t remember whether I liked it. I disliked Howl’s Moving Castle.
I also dislike Grave of the Fireflies on general principles and so have deliberately never seen it.
[quote=“dnooman, post:1, topic:628054”]
I’m trying to find some hidden gems worth watching. Maybe they’re not exactly hidden, but there are a lot in this list I haven’t even heard of. Bonus points if you figure out why they’re ordered this way. I’ve asterisked the ones I’ve seen and remember enough to have an opinion about, just for fun.
As you may have noticed I eliminated all silent movies save one, and all foreign films. I have seen some but just don’t care for most and the ones I do like you have not chosen so I did not rate them. Of the remaining films you have selected some of my all-time favorites (but not a lot of others.) In any case the best of the best that remain are numbered according to my preference. As you can see, you just cannot go wrong with Billy Wilder. But you are missing Preston Sturges, the Coen brothers and almost all of John Ford.
I will plug three of my all-time favorites not on this list:
The Lady Eve: Barbara Stanwyck; Henry Fonda
Viva Zapata: Marlon Brando; Anthony Quinn
Three days of the Condor: Robert Redford; Faye Dunaway
I didn’t say they were bad, just that you can reasonably skip them over. If you’ve seen 2001: A Space Odyssey, A Clockwork Orange, Dr. Strangelove, and the first section of Full Metal Jacket, you’re just as well to move on to Ran, The Seven Samurai, and Rashomon rather than to keep watching Kubrick films. The Killing is fine, Paths of Glory is fine, and Spartacus is fine, but they’re not the films that show off what Kubrick brought to the game.
And if you’ve watched Ran, The Seven Samurai, and Rashomon, you’re probably just as well to move on to Blue Velvet, The Elephant Man, and The Straight Story rather than go back and dig out Kurosawa’s greater anthology.
I noticed that the greatest movie of all time, *Raging Bull *is not on anyone’s list. So go ahead and watch all the others, because the very best will still be out there to see some day.
Gotcha - I just really like noirs, and I think that both The Killing and High and Low are terrific examples of them, two of the absolute best of the genre.
Is not! That’s the movie that gave me a years long crush on Cooper, damnit…
For a Western that’s in the list of “all those things you’re calling clichés were done here first” and which is not in your list, try Stagecoach. And I’m going to take advantage to plug one of my favorite Spanish movies, since I know it’s available in Parts Abroad with subtitles: Belle Epoque (when we rented it, my non-Spanish-speaking then-boyfriend stayed on the floor after falling off the armchair laughing for the second time).
I don’t think anyone has given props to or even mentioned the first movie on your list:
**Harakiri **(1962)
This is an amazingly good film.
Also, to me, **Ikiru **(1952) is Kurosawa’s best film. Maybe not his most entertaining, but his best.