You know... I've never really thought about it that way, but my three favorites may be the same most watched.
2001: A Space Odyssey
The Empire Strikes Back
Miller's Crossing
Sometimes I'll watch Miller's Crossing with English subtitles/captions, just to take in all that insane and masterful dialogue, it truly is as if William Shakespeare had written a 1920s mob tragicomedy.
You ain't got a license to kill bookies and today I ain't sellin'. So take your flunky and dangle!
Isn't Grosse Pointe Blank from around '98 or '99?
That's when VHS was on its' very last legs. I think my first DVD player was from around 2001, by that time the graph line of DVD rising and VHS falling had already intersected, and this was in Mexico, I'm not sure when other parts of the world made the transition, say in the US, Europe or Japan it happened earlier.
That mid-Almodovar peak was incredible, now that you mention it. My personal favorite from that time has to be Habla Con Ella (Talk To Her), in parallel Woody Allen filmography terms I would equate it with Hannah & Her Sisters, in artistic achievement.
Barry Lyndon is currently a rising "underrated masterpiece" topic with most of the best film critic podcasters. My personal favorite film has nearly always been 2001: A Space Odyssey, but I just recently rewatched Barry Lyndon and man... in any other filmography this would have stood alone at the top.
And we still have the rest of Kubrick's work to contend with... Dr. Strangelove, The Shining, Paths Of Glory, Eyes Wide Shut... it's just ridiculous.
For a long time now, I've regarded two people as my artistic heroes of the 20th century: Stanley Kubrick and John Coltrane. Mark Rothko could be up there, too, I cannot imagine my day-to-day life without his work to stop and look at, or to simply have as a presence in my surroundings.
"...the Rat Pack one with Frank Sinatra and Dean Martin!"
Imagine some crazy guy saying that.
This list of yours needs Werner Herzog's Aguirre and Fitzcarraldo in there.
This is Old School Cool catnip.
Is there an active Old School Cool instance around these here parts of the internets?
Oh lord... I LOVE Another Green World like few other albums in this world. Up there with Talk Talk's Spirit Of Eden and Laughing Stock, in my book.
I rather like the shitpost bombardment. It's the type of thing that creates a party vibe, and it could attract more than a few eyeballs to peek and linger. As the content can be somewhat dry in a community that's just starting out, this helps to normalize the place, make it more familiar to visiting eyes.
This current shitposting challenge sure as hell beats a barrage of anti-reddit, anti-musk, anti-zuckerberg posts, as well as "how does this [Fediverse/instances/posting/etc] work?" dominating the All page.
A blunt rewording of Seneca and Stoicism, leaning on the fatalism.
But now if I want to feel the spiritual and connectedness, I much prefer something like Van Morrison's Astral Weeks (I see your username and salute!), or John Coltrane's A Love Supreme. Stuff that challenges as it illuminates.
Musically, I've always been an enthusiastic searcher and have yet to stop delving, decades later.
One album that was tagged as New Age in the 80s that I still listen to every day - I use it for stretching before meditation - is Brian Eno's Music For Airports.
In the 80s, Ambient and New Age were clumped together uneasily but we didn't know better, until Techno came along and Ambient instantly found its' proper, logical home.
For a taste of some of the sound of groups like Wyndham Hill or Mannheim Steamroller - every element of rock n roll completely absent, a bit of medieval vibe wafting throughout - I now prefer a band like Pentangle.
There's one song I'd like to recommend to you at this moment - I can't get it out of my mind right now as I write - I discovered it about a year ago thanks to fantastic UK music monthly Uncut Magazine, it is closer in spirit to Brian Eno and it may have shot all the way to my #1 favorite piece of music ever. Listen to it in a quiet place, or with headphones. Often. This piece has a way of unfurling differently every time you hear it.
"Live on, survive, for the Earth gives forth wonders. It may swallow your heart, but the wonders keep on coming. You stand before them bareheaded, shriven. What is expected of you is attention."
Salman Rushdie, from The Ground Beneath Her Feet.
A more recent one, meditation-related, short and simple and I have no idea who said it, I just happened to catch it a couple of years ago on a website-that-shall-not-be-named:
"I am not my thoughts."
Meditation is better advice. By which I mean doing the exercises to approach grounding oneself in the present, sensing and feeling things from that perspective, instead of the YESTERDAY and TOMORROW clashing storms inside our minds.
But one can't just start meditating one day - "from zero to sixty", so to speak - and expect immediate results. It's a discipline, like brushing your teeth every day.