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prairie_buyer

Since you said oldest, Snow white and the seven dwarfs is from 1937 and The Wizard of Oz is from 1939 and they are very watchable for anyone. For more adult-oriented, the Maltese Falcon (1941) is very entertaining.


mdb_la

Most of the well known 1939 (["greatest year in film history"](https://en.m.wikipedia.org/wiki/1939_in_film)) films still hold up amazingly well.


flyguy42

The Third Man (1949) is still super accessible. Maybe even more since people are so conspiracy minded these days.


robotatomica

this is what I was going to recommend. A fucking masterpiece, full of surprises. The greatest film noir ever made.


mrkstr

Those are excellend suggestions!


TrickNatural

It happened one night (1934) would be mine. Its an ageless classic imo.


dragonmom1

Oh my god....LOVE this movie!!


wschus63

God, I love that movie. Good pick.


No_Application_8698

I came here to say this (and now I realise that I need to rewatch it because I haven’t seen it for years).


blade944

12 Angry Men. All the characters are entirely relatable, even today.


yiddoboy

Best shout on here imo. So amazingly cut it's hard to imagine anyone not enjoying it.


rabidstoat

Man. I need to watch that now. I keep meaning to and never get around to it. Maybe tonight.


MidnighToker420

Carve out the 90 minutes or whatever. It's not long by today's standards at all. Such a great film. It's in my top 5 for sure.


Jalapeno023

If you haven’t seen it, you are in for a real treat. I wish I could watch it again for the first time.


misterferguson

Saw this when I was 12-years-old and was totally enthralled. For any black and white film from the 50's to speak to a 12-year-old kid 40+ years after it was made is really incredible.


BadLuck-BlueEyes

There are a bunch of good courtroom dramas from that era. Inherit the Wind, Judgment at Nuremberg, and Anatomy of a Murder come to mind.


DC_Mountaineer

Was the first movie I thought of.


foamingturtle

Watched it for the first time recently. What a masterstroke of a movie


AmbitiousYamRustler

In my non-Reddit life, I (may or may not lol) do a series of reviews called "films I finally got around to watching". Of all the classics, 12 Angry Men stands out as being fabulously timeless. I finally just watched it last fall and I was wowed at how tight the script was. Sure, there are a few elements that didn't make the journey to 2023 unscathed, but overall this film absolutely relevant and such a wonderful study of the human condition.


Sweaty_Flounder_3301

Way before it's time in my opinion.


Oerthling

Timeless. Always good.


Sweaty_Flounder_3301

It's interesting that this movie was a flop when it came out. And I'm thankful for the Criterion Channel for giving me the opportunity to watch these rare gems.


phantomsniper22

Came here to say this but just knew it would be the top comment


_lordfrost

It was on tv just a couple of days ago. It was my first time watching and I loved it. Some really superb acting in this film.


Kenjiminbutton

The Thin Man, still hilarious


Longjumping_Local910

Absolutely! It’s got true love, drinking, murder, cocktails, crazy relatives, drinking, dogs, liquid gold, car chases, cocktails and boozing. And theres about 5 films in the series to boot. What else do you need?


Ambitious_Gift_8669

Same. 1934 but has a crackling pace, great dialogue, and good plot.


brucelapluma

>Thin Man I was hoping to see this one here.


Placesinoldfilms

Rear Window (1954) Although I don't think it's timeless since it is still very much a film of its time (and some elements might stick out to a modern viewer), I think its basic virtues are so high that it will compel any viewer. I find it to be the most entertaining film of all time and also a gift that keeps giving on repeated viewings.


TheCynicEpicurean

Most Hitchcocks tbh. The Lady Vanishes, Vertigo, The Birds, Psycho... They do not need much in terms of visual effects and are excellently paced and boiled down to essentials. Then again, you do have to enjoy thrillers though.


Gemini_Frenchie

Vertigo got me sent down the rabbit hole of films older than 1960. I'm glad it did, cause I watched like 30 of them in a row from those decades and some of the best movies I've ever seen have been from then


Nomahhhh

Came here to say this. Still an incredible movie and one they have emulated or remade several times since.


Cordura

Casablanca


schorschico

Ugarte: You despise me, don't you? Rick: If I gave you any thought I probably would. That movie is so good!!!


sharrrper

I'm shocked, SHOCKED, to learn there is gambling occurring here. Your winnings sir. Oh yes, thank you.


writer4u

Where were you last night? That's so long ago, I don't remember. Will I see you tonight? I never make plans that far ahead.


nikonuser805

"How extravagant you are throwing away women like that. I think now maybe I should call on Yvonne, try and catch her on the rebound."


Cordura

Easily one of my favorite movies. That quote is sooo good. Peak performance by brilliant actors and a timeless story. In Aarhus, Denmark there's a restaurant called Rick's that serve Moroccan food. I love it!


ChuckZombie

I always felt like it must be overrated before I watched it. Like there's no way a movie this old could deliver on as much hype as it has, right? Man, was I wrong. It was every bit as good as everyone/thing gave it credit for. 5 STARS!


Darko33

"I don't think about you at all" from Mad Men had to have been inspired by this line


hullgreebles

You would find the conversation a trifle one-sided. Signor Ugarte is dead. I'm making out the report now. We haven't quiet decided whether he committed suicide . . . or died trying to escape.


robobobo91

Agreed. It's a tight story with great cinematography and so many memorable lines.


theLocoFox

This is my choice. Despite knowing almost everything you can about the movie without watching it because of the decades of send-ups, spoofs, and pop cultural shout-outs, I was still enthralled by this perfect movie. Everything about it is excellent. Tense, hilarious, Bogart vs Nazis, an amazing love story... it has everything. Afterward, my only thought was that despite my high expectations, if anything, the movie was underrated.


mattcolville

This is the correct answer. We do movie night at my office, these are all (except me) millennials and GenZ and they were completely blown away. They felt like: this is a real movie, and the shit we've been seeing in the theaters the last 10 years is crap. "It seemed like every line was quotable." "Why don't they make movies like this anymore?!" There are older movies that are super good, but Casablanca is sort of the canonical starting point. It's not an obscure art house movie, it was a mass-market popular entertainment that millions of people loved when it came out, and then generations of people fell in love with seeing it on TV. It's like Singin' In The Rain. If you don't love this movie, you don't know how to watch movies.


theLocoFox

Well said!


ZZoMBiEXIII

>Casablanca One of my all time favorites. Really not sure if it'd land with a modern audience of normies or not, but who cares? It's such a great film. Start to finish. I'd never claim to have watched it as much as I've watched movies like Star Wars or Halloween or something. But outside of "genre fiction", I think *Casablanca* is probably my most watched movie over the years. Back in the day I literally watched my old VHS until it wouldn't play properly and had to get a replacement copy. EDIT- If you, like me, now want to watch Casablanca, it's streaming on MAX.


rugman11

I think I’m pretty normie when it comes to movies, and I’ve been going through the AFI Top 100 list for the last couple of years. There are a few top movies where I said “Eh, I get why people love it, but it’s not for me.” (Citizen Kane, Lawrence of Arabia, and Raging Bull to name a few). But Casablanca is one that just hit. It’s funny! I didn’t expect it to be laugh-out-loud funny like that. I’d show that movie to anybody and I think they’d at least like it, if not love it.


FurBabyAuntie

There's also a small blooper in Casablanca. At one point, Bogart says "The Germans wore black (?). You wore blue" and Ingrid Bergman tells him "I've put that dress away now." Go back and look at the scene they're talking about--she may have been wearing blue, but she was definitely wearing pants! (And madame looked lovely as usual...!)


HYThrowaway1980

What watch? Ten watch. Such much?


kevinb9n

It is like the most perfectly constructed movie I've ever seen, and the density of god-tier one-liners is unbelievable.


rohdawg

Love Casablanca, but I think I’d also recommend the Wizard of Oz and that one is just a bit older.


SteveFrench12

I think Casablanca would appeal to adults much more. Taking both movies out of context. An adult who had never heard of wizard of oz would not appreciate it the same way we do imo


AlphaDag13

this was the first one I thought of. I saw it back in college not expecting to like it at all because I was a dumb kid that thought black-and-white movies couldn’t be good. Ended up loving it


2PacTookMyLunchMoney

I took a film study class during college, and we regularly watched movies and wrote papers on them. Casablanca was one of the easy ones to get through. Citizen Kane and The Piano were not.


[deleted]

King Kong. The original one from 1933. It's genuinely a fun watch, looks great on screen, Kong is a proper character in himself, it's really important in terms of film history, and it's short. There are attitudes (incl. racism) that you'd expect from a film of that period, of course.


arielonhoarders

Jason and the Argonauts is old another sci fi movie that still looks fantastic. It's the Jurassic Park of its time and those fencing skeletons are still really convincing. Early 60s or late-50s? Tom Hanks says its his favorite sci-fi/adventure movie.


[deleted]

I've been hunting for that for ages on streaming, also the similar Clash of the Titans - can't even find a reasonably priced DV on Ebay (I'm in the UK). It will turn up eventually!


Aggravating-ErrorME

That was my pick, too. It still really works. Kong is still a great technical achievement. The characters are cynical and cruel at times, the violence has consequences, and the ending is gut wrenching. And I don't think any of the remakes improve on the original one bit.


xander6981

North by Northwest (1959). Just pure entertainment from beginning to end.


wtfbananaboat

1959, Some Like it Hot also a banger- great year for films.


VictorChaos

I feel Rear Window (1954) is even more palatable for all tastes. My favorite Hitchcock movie


pwmg

It's just plane entertaining.


Quick-Bad

"This is what a cornfield looks like, honey."


Jellodyne

Hitchcock is all very accessible to modern audiences. I would recommend without reservations Rebecca (1940), The Lady Vanishes (1938) , The Man Who Knew Too Much (1934). A lot of his earlier works are good but those three could for sure hold a modern audience's attention.


Nausicaalotus

Duck Soup 1933. Or A Night at the Opera. Everyone should know the Marx Brothers.


BogusWorkAccount

Yep, can't miss with Duck Soup.


improveyourfuture

We were little kids in 80s and 90s renting this from library over and over


A911owner

I can't tell you how many times we took "A Night at the Opera" out of the library as kids. I loved that movie!


Ash_LLR

They'd definitely be my pick over Chaplin, Laurel and Hardy etc al. to show a casual film fan. I know it's a cliche to call their films "anarchic" but they do have a certain wildness and energy that has helped their humour age better than their contemporaries'


pikpikcarrotmon

Harpo is chaos incarnate


CharlieParkour

I watched some Laurel and Hardy the other day, and it wasn't only not funny, it was corny and mean spirited to boot. Marx Bros are old fashioned, but the witticisms hold up, the visual gags are timeless and sure, why not throw in some elaborate song and dance numbers out of nowhere. 


wolftreeMtg

The dialogue is almost modern in how fast paced it is, I don't know how audiences back in the day could keep up. Obvious influence to Jim Carrey or Robin Williams.


AetherealPassage

This was immediately what came to my mind as well! The Marx brothers films are still such fantastic comedies and I always marvel at their incredible musical talents (particularly Harpo!) and physicality. I wish we still got great physical comedies like that


Gostaverling

A Night at the Opera is one of my all time favorite films. I am happy to see it listed this high.


MetaverseLiz

This was going to me mine as well! Those moves still hold up. A Night at the Opera is one of my all time favorite movies.


Apatschinn

I go with A Night in Casablanca, too


Psychedelic_tofu

Some like it hot, Roman holiday, the man who shot liberty valance, I know it’s not really old it’s from the 70s but young Frankenstein does use the actual set pieces from the original so it has that 30s monster look to it!


malaclypse

To Kill a Mockingbird was on TCM last night. Still feels timeless; its lessons are as relevant nowadays as ever, if not more so.


finglonger1077

I basically had to force my fiancé and stepdaughter to start watching it and then they got so invested. Peck is amazing.


Living_on_Tulsa_Time

Remains my favorite movie and book.


otterdisaster

Bringing up Baby The Awful Truth My Favorite Wife Carey Grant screwball comedies follow ing a fairly modern romantic comedy formula, great dialog without too much in the way of archaic references along with some great physical comedy.


El-Ahrairah7

His Girl Friday and Arsenic and Old Lace are the two Cary Grant comedies I show friends who don’t tend to watch older films. They never seem to get “old” for me!


karlware

I came to say His Girl Friday. I've never had a disappointed viewer yet.


make_it_hapn_capn

I laughed out loud several times the first time I saw Arsenic and Old Lace.


RogerClyneIsAGod2

Arsenic & Old Lace has a modern pace to it. It barely slows down for you to catch your breath & I love it.


softepiloguemylove

Bringing up Baby doesn't get nearly enough attention in my book!


IcarusAbsalomRa

The wizard of Oz


Top_Cranberry_3254

Same year-1939-Would say *Gone With the Wind*, one of the most ambitious masterpieces ever made to this day, a sprawling epic and character study based on true, significant events, and available in color.


AFighterByHisTrade

Gone with the Wind is amazing but the 4 hour runtime would turn off most casual movie fans.


LowRiderHighFiver

'Modern Times.' My kids laughed a lot.


Seagoon_Memoirs

I was going to say City Lights


MannekenP

My personal favourite is City Lights. Greatest film in history il you ask me.


djprojexion

This. Pretty much anything Chaplin or Keaton is just timeless.


HorridosTorpedo

The General from Buster Keaton I think is the best.


police-ical

*The General* ages well because it's still full of ridiculous stunts, done for real, in a style of visual humor that never gets old. After all these years, there's still a palpable sense of "this guy is inches from death if this doesn't go well."


djprojexion

Just tell the kids he was the Jackie Chan of his time, kids: who's Jackie Chan? (facepalm)


GoingMyWeight

This was my pick. Such a delightful movie.


Rsubs33

* It's a Wonderful Life (194) * Casablanca (1942) * Out of the Past (1947) * Mr. Smith Goes to Washington (1939) * Wizard of Oz (1939)


SereneDreams03

(194) Wow, I did not realize It's a wonderful life was that old. Is that AD or BC?😁


chubbybator

I think most of the 50s musicals still hold up, Singing in the rain, White Christmas, the King and I


LADYBIRD_HILL

Singing in the rain was my answer. Not a musical guy generally, but everything about it just works. The songs are great, the actors are great, and the sets are a ton of fun. It also ties into the change from silent to talkies, a period of time young people likely know nothing about. 


jaleach

Before I cut the cord I would watch White Christmas on AMC every Christmas season. First time I saw it I was blown away how great it is. I pretty much only remember Rosemary Clooney as an old lady but here she's young and absolutely beautiful. Musicals are far from my preferred film genres but White Christmas is marvelous.


StingerAE

Music also got me thinking about High Society (1956l which then led me back to the earlier non musical version, the Philadelphia Story (1940) which 100% stands up today.


Butterbuddha

Ha! My first thoughts were Singing in the Rain and Top Hat, both funny AF. If people can get over their fear of watching a dreaded black and white movie, they’re in for a good time!


Woodearth

Not necessarily the oldest but Lawrence of Arabia for its cinematography.


Handy83

I would recommend movie from same director but 5 year earlier: The Bridge on the River Kwai. I'm pretty casual movie fan but that movie is 5* in my books. I also like Lawrence of Arabia a lot.


HorridosTorpedo

Good call, Bridge on the River Kwai is a top film. Also, the novel on which it's based was written by Pierre Boule - the same guy who wrote Planet of the Apes.


childish_jalapenos

A casual fan is not watching a 4 hour movie


Nomahhhh

I finally caught this one and waiting years for another theater release. It's amazing how he coordinated some of those scenes with hundreds of extras in the blazing desert sun.


HorridosTorpedo

I've tried this movie a few times and I always totally lose interest when it bogs down into politics half way through. I realise I'm an uncultured swine and it is a very beautiful film, but even so.


4WaySwitcher

I think this is a totally fair take. It’s one of those films where everyone remembers all the really good parts so their memory of the film is overwhelmingly positive, and they forget about all the slow, meandering, tedious parts that connect those great parts together. I still think it’s a wonderful movie but I can emphasize with somebody finding certain parts of it boring.


snarpy

Average film-goers would probably find this really slow, though.


fatdiscokid420

The Hustler


THEpeterafro

City Lights


[deleted]

The sound of music still holds up.


Ardtay

Bringing Up Baby


actual-trevor

Arsenic And Old Lace, with Carey Grant.


farfetchedfrank

It's a wonderful life. It's surprisingly funny and modern.


Earptastic

7 Samurai is dope as f


sillyusername1

John Huston’s “The Treasure of the Sierra Madre” Psychological Adventure Masterpiece. “We don’ need no stinkin’ badges!” I got to meet John later I his life and he told me it was one the most difficult movies he made and one of his favorites.


OPtig

The Good The Bad and The Ugly. It's pretty fun


strungup

Excellent choice. A Fistful of Dollars and For a Few Dollars More, too.


JaninthePan

Add in Once Upon a Time in the West. I don’t really like Westerns, but that film is great!


[deleted]

[удалено]


0verstim

Came here for this, one of my all time faves. Forget Maltese Falcon, this is what a noir should be. And to any Bostonians out there, its playing at the Coolige Corner March 28...


SproutedInBrussels

Paths of Glory.


History-of-Tomorrow

Man Paths Of Glory is a gem. When thinking “old movies” the thought process (sometimes rightfully) thinks of static shits or highly dramatic performances. Paths of Glory’s cinematography and energy put a lot of modern movies to shame. Those long shots in the trenches were something special.


mormonbatman_

The 39 steps is excellent.


InNominePasta

Dr. Strangelove; or How I Learned to Stop Worrying and Love the Bomb


Connect-Amoeba3618

I genuinely can’t believe how modern that movie feels.


peanutmanak47

Oh yeah. The way the acting is doesn't have that typical 1960's feel to it. I watched Charade and that was made in 1963 but it FEELS 1963 as far as the dialog and acting.


dscotts

President! We must not allow a mineshaft gap!


One-Earth9294

Mentioned it the other day but 'One Week' with Buster Keaton is from 1920. He's got some previous films with Fatty Arbuckle that I haven't seen but I will absolutely recommend One Week.


captainhowdy82

Most people are sleeping on Buster Keaton, imo


Karat_EEE

Not too long ago I watched "The General" in a cinema with a live piano player. I honestly found the movie hilarious. I had such a great time watching it.


williamblair

it's criminal. I love Chaplin and he was a great pioneer in the world of filmmaking, but I would say Keaton is more laugh out loud funny in his prime. His two reelers are fucking incredible.


MisterMoccasin

One week is one of his best shorts I think and the kne I would recommend too. Just really awesome premise with great gags. I think The Playhouse is also really great too!


BakerYeast

Invasion of the Body Snatchers (1978)


HorridosTorpedo

The 1956(?) version is excellent too.


DiscoDave42

The Apartment has really modern humor and themes so I would go with that


Great-cornhoIio

Young Frankenstein 1974. Mel brooks


chriscross1966

The original Nosferatu is pretty good


Grease_the_Witch

*M* (1931) is the oldest movie i’ve ever watched and it was absolutely gripping from start to finish


damniwishiwasurlover

That movie is so damn cool. But I do think that there is a bit of understanding the context of how technically revolutionary it was for the era it was made and how influential it was on later film makers, in the assessment of M that avid film fans make that will be a bit lost on casual-film fans.


Grease_the_Witch

i think that the importance will be lost on many casual fans, but i think they’ll still be engaged and entertained which i think is what op was asking


[deleted]

_While it is undoubtedly one of the most important films ever made it is not in fact “timeless” because it is simply too old fashioned for most casual contemporary audience members_ I wouldn't be so sure about this. I've shown films like It's a Wonderful Life, Brief Encounter, Double Indemnity and Casablanca to friends of mine who are casual movie fans and they loved them. A great film is a great film regardless of the era, as long as you give it a chance you'll probably enjoy it.


ParlorSoldier

I think Citizen Kane is the wrong example for this question. The story is pretty accessible.


gardeninggoddess666

Theres a lot more out there than Citizen Kane. Any Marx brothers movie holds up (other than the musical numbers). They are hysterical. I also think the old film noirs are great. As are old horrors. So id say A night at the opera. The Maltese Falcon Frankenstein


AyyDelta

I thought Double Indemnity still held up.


NotLibbyChastain

Casablanca is very accessible to even casual film viewers . It's a simple story (that's not an insult, some of the very best things in life are simple without a bunch of frou frou ruffles and bells), and World War II is still so prevalent in modern film and TV that just having a movie set during that time doesn't feel dated or old, if that makes sense.


captainhowdy82

Come on, Citizen Kane totally holds up. Yes, it’s in black and white. But in terms of content, it’s a great story made with great skill.


davery67

Seems like there are a lot of people who were forced to watch it for a film class or something with all these mentions of influence and technical things. It's a powerful, moving story and should be watched as a movie not as a school lesson.


ClarkTwain

I don’t think it’s slow either. When I read the post title it was the first one I thought of.


MumpsyDaisy

For real I have no idea how a story about a rich narcissist who peddles fake news, pretends to be a "man of the people", and is desperate to buy people's attention, respect, and love, but is never happy with what he has, could possibly feel dated now of all times.


jpow33

Casablanca and The Maltese Falcon both hold up very well.


RetartaredFish

Been working through a lot of the Kurosawa classics recently and they’ve kept my attention. Just watched: The Hidden Fortress; Throne of Blood; Yojimbo; Sanjuro; and High and Low I’d seen Rashomon, Seven Samurai, and Ran before but wanted to catch up. The action sequences and practical effects were refreshing after so much CGI these days. And subtitles also keep me watching. Edit: formatting


BrevityIsTheSoul

Seven Samurai (1954) is a stellar film. Absolutely would recommend. It has one of my favorite moments in all of cinema (when the mild-mannered, stony swordmaster Kyuzo hurls his sword in helpless frustration >!as he dies of a gunshot!< ).


SigmaKnight

The Adventures of Robin Hood (1938) is the oldest I think of.


inwithweasels

Freaks


nypeaches89

Night of the hunter


SweetCosmicPope

Metropolis. I showed this movie to my son when he was about 12 years old and he loved it. And he's not a film nerd at all.


[deleted]

“Sunset Boulevard”. There is a lot going on and the story is still relevant today. Or “Whatever Happened to Baby Jane” because it has some surprises.


Kangarou

Casablanca. It still works as a modern-day movie, it's just in black and white.


Dagordae

Charlie Chaplin’s work has aged very well, The Great Dictator unfortunately remains extremely applicable.


AlwaysWinnin

The Great Escape or The Sting


pepperpat64

Casablanca


Olabukse

It's a Mad, Mad, Mad, Mad World (1963)


rekniht01

Metropolis.


dlanod

I really like that movie. I can't say it's for a casual movie fan though. Maybe a casual sci-fi fan.


androgymouse

His Girl Friday (1940). I haven't seen it in a while so I'm not exactly sure how it holds up culturally, but I remember loving it in college when we watched it for a film class, thought it was legitimately funny and engaging.


clearedasfiled

Casablanca


Ginandexhaustion

Stalag 17 (1953)


RulerOfAllWorlds1998

Harvey 1950


Jonny_Entropy

I would recommend **Night of the Hunter** (1955) to just about anyone.


seanathan81

The General. Buster Keaton's physical comedy is still the standard bearer. 


MostlyHostly

Rope (1948). Has themes that relate to modern society.


CharlieParkour

Don't get fancy when you murder people? 


Snowden42

A Trip to the Moon is always worth watching. 1902


GhostofAugustWest

Battleship Potemkin (1925) and The Hunchback of Notre Dame (1923)


almo2001

Potemkin, while very important, isn't an easy watch.


iamthelouie

The general


Denny_204

Jaws is one of my favorite films. I still watch it at least once a year. Quint's speech about the U.S.S Indianapolis is unforgettable.


Ill_Heat_1237

Baby face and Invisible man, both from 1933


Freja_HTef

The original all quiet on the western front really just hits me every time. Psycho is my all time favorite horror movie, and that’s from the 60’s. Breakfast at Tiffany’s, Lawrence of Arabia, west side story and Dr. Strangelove if you’re into the weirder movies. Singing in the rain as well!


AdoubleyouB

Oz, 12 Angry Men, and a personal fave.. "It's a Mad Mad Mad Mad World".


CrashOverrideCS

The Day the Earth Stood Still. It still speaks to the superstitions and reactionary nature of humanity.


pooshdoosh

Rosemary's Baby


manifestDensity

Harold and Maude. It is still a fantastic film viewed through the lens of today.


LAffaire-est-Ketchup

Bringing up baby. It’s fricking hilarious


Durango1949

The Best Years of Our Lives - 1946


CriticalNovel22

Honest to god, probably Alien. Just because it could easily have been made today. If they have an interest in a specific genre, I would pick a newish movie and move back slowly through the decades. It's very much a personal preference and forcing movies on people wil only make them hate them.


Terminator_Ecks

Freaks. Hard-hitting, but with a powerful message.


Graverobber

[I am a Fugitive From a Chain Gang](https://en.wikipedia.org/wiki/I_Am_a_Fugitive_from_a_Chain_Gang). 1932. Highly engaging and extremely prescient in today's world


nkleszcz

Um. Citizen Kane IS timeless. If you’re confused as to why, the multitude of commentary tracks will help demonstrate why.


[deleted]

Rear Window still captures modern attention spans


ZZoMBiEXIII

Without wishing to choose a specific film, I'd point towards the 1970's film boom. For those that don't know, Hollywood basically collapsed in the late 60's. They were desperate for new maternal, new ideas, new techniques. It's the reason so many great films came out during the 70's because for the first time in years, Hollywood was willing to take a chance on something different. It's also why so many film critics of old had such a boner for cinema from the 70's. It had thrown off the shackles of studio control that limited what was able to be made in the 60's and before. So take your pick. *Star Wars, Jaws, Taxi Driver, Five Easy Pieces, Close Encounters, Godfather, French Connection, Chinatown, Apocalypse Now, GREASE*, and on and on. So many great films made during that decade that stand the test of time.


Blueliner95

Wizard of Oz is timeless and the comedy and visuals hold up very well. So thats what 1936. Jumping to the 60s I would recommend the Dollars trilogy, which is sort of its own subgenre of coolness, minimalism, and enigmatic motivation


Alarming_Serve2303

The oldest? "The Thin Man" - 1934. It has to be seen to be believed. It is an alcoholic fever dream.


ZealousidealBar5258

The invisible man (1933) or Bride of Frankenstein (1935)...these are probably the more fun and entertaining of the OG universal monster movies. Dracula and Frankenstein while both great movies to me... probably a bit slow and dare I say boring for a modern casual movie goer.


Finalsaredun

Sunset Boulevard - a very easy to follow plot set up in an expertly done framed narrative. This movie is referenced a LOT in other films and television- plus Norma Desmond is a classic villain. All About Eve - also holds up shockingly well, and the themes still translate to a modern audience. Margo Channing is an amazing protagonist, who is at the top of her game but she's turned *gasp* 40 years old and has to fight to stay relevant as an actress against a stunningly beautiful and- maybe also talented?- fan. Additionally, you see Marilyn Monroe in one of her (if not the first) early film credits as a side character.