Freeway: awesome, twisted, fairly obscure movie starring Reese Witherspoon and Kiefer Sutherland. I’m not a Reese Witherspoon fan at all, but this is one of her earliest film roles and is really amazing in it.
Seen it. 
Are you familiar with the works of Buster Keaton?
I’m like an anti-film buff in that I have probably only watched around 100 films in my life (yes, really) but based on the few on your list I have seen (or at least am aware of), I get the impression you might like films with a weird twist at the end that immediately makes you want to watch the film again. To that end, I offer The Prestige and Lucky Number Slevin. You’ve probably already seen them, though.
I watched that this evening, not really knowing what it was about beforehand. Yes, I did finish it. It was weirder than “Eraserhead”, and that is saying something.
Safety Not Guaranteed - a group of reporters investigate a guy who has placed a personal ad looking for someone to time travel with him.
I’ve seen a great many of these, excellent suggestions!
I’ll add Rubber about a homicidal car tire that gains self awareness.
Amelie, because no one does weird like the French; and if you can handle the subtitles, Le Diner du Cons which was remade with Steve Carell as Dinner For Schmucks. The French is much darker, I thought.
I also thought Guardians of the Galaxy was a great romp.
Finally, I liked Replacement Killers, and The Professional if you need to some shoot em ups.
You might check out Kids by the same director. It’s not as strange as Gummo, but yet still captures the nihilism of youth.
Given there are two Charlie Kaufman movies in your top four you have to watch Synecdoche, New York immediately. It’s a mind bending existential film with lots of symbolism, mostly depressing but with some dark humor. Not exactly a light popcorn flick. One of those movies that rewards a second viewing.
That was one of the dumbest movies I’ve ever finished. :rolleyes: It’s not really about time travel, and the main character was one of the most unlikable characters I’ve ever seen.
What kind of 38-year-old man is obsessed about his co-workers’ virginity status, anyway? 
Some great new ideas from this older thread. Some of the films I’ve seen; (Safety Not Guaranteed, Amelie, Le Diner du Cons, Kids, Synecdoche, New York,) and some I haven’t.
I saw Birdman and was surprised that I didn’t like it nearly as much as I thought I would, (but I LOVE the way it was filmed! It just seemed like one long take, but the flow of the film was good - I just wasn’t a big fan of the story or the ending.)
So, yeah… if anyone has any other flix in mind, I would love to hear them. I have my plate full now with Netflix rentals. ‘About A Boy’ is great so far… I just had to take a break from the movie because it’s so long. I’ll finish it Monday.
BTW, a fun site for looking up movies is http://www.jinni.com/ You don’t have to join, sign up, or even sign in. Just click on the orange “moods” button, make some choices, and it will suggest movies. The data base, alas, is NOT vast.
A few more you might consider:
Blindness
When a plague of blindness overtakes an entire city, all sense of order breaks loose in the hospital where the victims are being quarantined. Now, it’s up to a woman who’s keeping her sight a secret to lead a group safely to the streets.
John Dies at the End
A new street drug that sends its users across time and dimensions has one drawback: some people return as no longer human. Can two college dropouts save humankind from this silent, otherworldly invasion?
Kiss Kiss Bang Bang
A murder mystery brings together a private eye, a struggling actress, and a thief masquerading as an actor.
Only Lovers Left Alive
Depressed over the state of the human world, underground musician Adam – a vampire – hooks up again with Eve, his mysterious lover of many centuries. But the antics of Eve’s spirited little sister threaten to destroy their eternal love.
Run Lola Run
After a botched money delivery, Lola has 20 minutes to come up with 100,000 Deutschmarks.
About A Boy is new information; I wouldn’t have recommended it based on your list in the OP. One of the ones I was going to recommend (going through all my 5- and 4-star netflix ratings) was 500 Days of Summer, which was already in your list.
There’s more to the movie. What makes it really interesting is that it shows the same scenario over and over, each time with slightly different actions yet similar results.
If you haven’t already, I’d suggest you discover the screwball comedies of the golden age of Hollywood. Some of the very best are The Awful Truth, Ninotchka, Bringing up Baby, My Favorite Wife, You Can’t Take It with You and It Happened One Night.
You also might like the independent films from the 1980s, when Hollywood was extremely formulaic, before Hollywood noticed that people were going to the independent (and cheaply made) films in droves, and started being a little more experimental in the 90s.
Check out Stranger than Paradise, Night on Earth, Hannah and Her Sisters, Return of the Secaucus 7 (actually from 1979, but first film from prolific 80s director John Sayles), My Brilliant Career (also technically 79, but released in the US in 1980), and other films from John Sayles and Jim Jarmusch.
Also, in the 80s, Spanish director Pedro Almodovar released the closest thing to a modern screwball comedy I’ve ever seen, called Women on the Verge of a Nervous Breakdown. It features a kind of nerdy Antonio Banderas before his Hollywood makeover.
If you liked The Bride of Frankenstein, you would probably like the initial films in all the Universal monster series, before they degraded into silly, but IMO, kinda fun, sequels. There’s the original Frankenstein, the Lugosi Draula, the original Wolf Man, with Lon Chaney, jr., as well as the earlier Werewolf of London, and the original Mummy with Boris Karloff. All are highly recommended.
Based on your list, I assume you have seen the original Planet of the Apes, but if not, you should. Not the sequels, just the original. Also, if you are very young, and have never seen Star Wars aka, pt. IV “A New Hope,” see this. Just this.
Try Passport to Pimlico, a little British comedy where a neighborhood of London becomes and independent nation.
Also Good for Nothing, a Western from just a few years back about an outlaw who’s frustrated by an inability to repe his hostage due to erectile dysfunction, who searches the west for a cure.
Based on some of the above, such as Truman Show and Eternal Sunshine, I’d say try 1997’s The Game, with Michael Douglas and Sean Penn.
Similar sort of “immersive experience”, “try to crack the nut while the main character is doing the same” kind of vibe.
Speaking of The Game – you might also enjoy a screwball variant of it, The Man Who Knew Too Little with Bill Murray thinking he’s participating in a street theater game, but he’s not.
Try The Saddest Music in the World, a satire of 1930s-era films, with Isabella Rosellini as a filthy rich double amputee who offers a cash prize to the musician or band who win an American Idol-type competition.
According to Roger Eber, “This plot suggests no doubt some kind of camp musical, a sub-Monty Python comedy. What Maddin makes of it is a comedy, yes, but also an eerie fantasy that suggests a silent film like “Metropolis” crossed with a musical starring Nelson Eddy and Jeannette McDonald, and then left to marinate for long forgotten years in an enchanted vault.”
The movie is truly inexplicable in description, think along the lines of North Fork (which I also highly recommend).
Sorry it took me so long to reply.
I’ve seen:
Kiss Kiss Bang Bang
Run Lola Run
Stranger than Paradise
Most of the Universal monster series
Planet of the Apes
The Man Who Knew Too Little
Good suggestions!!
I’ll come back to this thread every now and then to see what I want to watch next. 