Saw this listing over at a Townhall Blog.



Okay, so... not my list., but then I've only seen 2 of those movies. (Mobster/organized crime movies don't do anything for me.)

Here's mine, in no particular order:

1) The Matrix
2) Pay It Forward
3) The Fifth Element
4) The Truman Show
5) True Lies
6) Die Hard
7) The Transporter
8) Crouching Tiger, Hidden Dragon
9) Unforgiven
10) The Sixth Sense

What are yours?

In no particular order:

1) Die Hard

2) Goodfellas

3) Heat

4) Pulp Fiction

5) Terminator 2: Judgement Day

6) Ocean's Eleven

7) Casino Royale

8) Children of Men

9) Se7en

10) Anchorman

Another fundamental disagreement! I love mob movies

No order

1-3.) The Lord of the Rings: They we're all so very good...
4.) Carlito's Way
5.) Goodfellas
6.) The Matrix
7.) Casino Royale
8.) Braveheart
9.) Munich
10.)The Departed

Edited to point out Munich was cooler than Gladiator.
I assumed we were leaving out the anime.

Jin-Roh.

Samurai X.

Respect.

Since 1987...

La Cité des enfants perdus. Jean-Pierre Jeunet. 1995.
Le Fabuleux destin d'Amélie Poulain. Jean-Pierre Jeunet. 2001.
Way of the gun. Christopher McQuarrie. 2000.
Donny Darko. Richard Kelly. 2001.
Nikita. Luc Besson. 1990.
Black Hawk Down. Ridley Scott. 2001.
Gladiator. Ridley Scott. 2000.
Le Pact du Loup. Christophe Gans. 2001.
Leon. Luc Besson. 1994.
Ghost dog, the way of the samurai. Jim Jarmusch. 1999.

In no particular order:

Dark City (1998)

Sin City (2005)

Hard-Boiled (1992)

One False Move (1991)

Sexy Beast (2000)

Kill Bill Vol. I (2003)

Desperado (1995)

Face/Off (1997)

Devil In A Blue Dress (1995)

Collateral (2004)

and I could have easily included, L.A. Confidential, Heat, Children of Men, Ghost Dog: Way of the Samurai, Leon (aka The Professional, La Femme Nikita, Reservoir Dogs, The Usual Suspects, The Long Kiss Goodnight, Casino Royale, Miami Vice and so many more, but a lot of those were already mentioned.

The main problem I have with movie lists is narrowing my selections down to several dozen - never mind ten. This one was particularly challenging in that I wasn't sure what exactly constituted "cool". Barnett's "fresh and original" and "something that some people get and other people don't" didn't quite do it for me. Nor did his "you know it when you see it". The Princess Bride and Edward Scissorhands, for example, are cool (even by Barnett's quasi-definition) - but are they "cool"?

I'll suggest that "coolness" primarily has to do with attitude: Sean Connery's James Bond and Steve McQueen's Bullitt are undeniably cool. The Brat Pack is definitely cool in Ocean's 11 - as are Clooney, Pitt, Damon, et al. in the remake. But what makes these characters - and their vehicles - cool? There's usually an element of danger or risk-taking - which often involves espionage, crime, or cons - allowing the protagonist to remain somewhat aloof in the face of various threats. There's a certain level of sophistication in the development of the narrative and in the dialogue - and a level of artifice to the visual look of the film. "Cool" movies are often something of a pastiche, recalling or appropriating conventions from established forms, most often film noir - and generally have a self-conscious sense of style. A lot of films come close, but don't quite achieve "coolness" for one reason or another. Angel Heart has a lot of the right elements, but is ultimately a bit too creepy to be cool; Down with Love has the characters, the dialogue, and the look, but not enough edge to be "cool" - it's too nice.

So... bearing all of that in mind, I started winnowing down my list and came up with the following as a top ten (alphabetically - I'm even worse at ranking than at selecting):

Confessions of a Dangerous Mind

Fight Club

Jackie Brown

Kiss Kiss Bang Bang

LA Confidential

Memento

Miller's Crossing

Sin City

Trainspotting

The Usual Suspects

If I had to single any films out, I'd go with Kiss Kiss Bang Bang and Confessions of a Dangerous Mind, two of the most underrated films of the past few years - as well as Jackie Brown (Tarantino's best film) and Miller's Crossing (the Coen Brothers' best film), which also tend to get a bit overlooked.

Those not quite making the cut: The Bourne Identity, Catch Me If You Can, The Cook, the Thief, His Wife, and Her Lover, Collateral, Copycat, Crimes and Misdemeanors, The Departed, Die Hard, Dogma, Drugstore Cowboy, La Femme Nikita, Fresh, Grosse Pointe Blank, The Killer, Last Man Standing, Law of Desire, Léon, Live Flesh, Match Point, Mulholland Falls, New Jack City, Old Boy, Reservoir Dogs, Run, Lola, Run, Snatch, Things to Do in Denver When You're Dead, Training Day, True Romance, Twelve Monkeys, 2 Days in the Valley, and Wild at Heart.

Well, my definition of "cool" may not be the same as everyone else's, but here goes - in no particular order...

The Usual Suspects - doesn't get much cooler than Keyser Soze!
Shi Mian Mai Fu (House of Flying Daggers)
The Princess Bride
Memento
Lola Rennt (Run Lola Run)
Big Fish
Lock, Stock and Two Smoking Barrels
Frida - I loved the movie, but the cinematography is what made it cool
Fresh - not very well known, but great nonetheless
Me and You and Everyone We Know - because it's just so darn weird, it's cool

Honorable Mentions: Office Space, Leon, The Silence of the Lambs, The Sixth Sense, Toy Story

I'll throw my nominations in the ring:

In no particular order:

Lord of the Rings trilogy
Sin City
Gladiator
Big Fish
The Matrix
The Lion King
Enemy Mine
Jurassic Park
Titanic
Mars Attacks!

Your mileage may vary.

In no particular order (defining 'cool' is difficult for me, I'm a nerd and yes, damnit, Babe was cool )...I agree with Wertz that narrowing this down is impossibly difficult. I'm sure I've made several other lists for similar topics during the past four years and am contradicting myself now. But these are the ones that come to mind at the moment.

Lord of the Rings
Love, Actually
Pulp Fiction
City of God
Big Fish
Trainspotting
The Sixth Sense
Babe
Underworld
The Others

Edited to add: Fun topic! I'm getting some ideas for my Netflix queue from the lists here (I just added Fresh, which I had never heard of but sounds really good! Also Nikita, which I hadn't thought of renting but sounds great, as well as edgy and my favorite genre style of movie...). Thanks.

Edited again to replace The Sandlot with Underworld, doh!

Ohhh how can Ferris Bueller's Day Off be over 20 years old? That would mean... noooooooooooooooooooooooooooo!

So:

Goodfellas
Trainspotting
Best In Show
Reservoir Dogs
300
Spiderman
Pushing Tin
Underworld
Bring It On (that's right... I liked that movie. So what?)
The Sixth Sense

1. Lord of the Rings (any)
2. Chronicles of Narnia
3. Dune (miniseries-- movie cool, but too old)
4. Harry Potter (any)
5. The Matrix (#1 only, #2 and #3 were stupid)
6. Terminator 2 (T1 is too old, T3 was not very cool)
7. Jurassic Park (any)
8. The Game (1997)
9. Sneakers (Redford, Poitier, Kinglsey, Akroyd, McDonnell, James Earl Jones, etc., in a spy-fugitive-hacker action-comedy-thriller; geek-cool)
10. National Treasure (Cage is not cool, but good action comedy)

Runners up: Babe (#1 cooler than #2), Eragon, The Ring, The Others, most of Night Shyamalan's stuff, most superhero movies, Clancy movies, historical fiction, political intrigue, and mystery-- apparently they're ranking lower than 10 with me on the cool scale today. Some greats like Schindler's List and Shawshank Redemption are far too heavy to call them cool.

Cool, but old: Few of the Star Wars or even-numbered Star Trek movies new enough to qualify are cool enough for the list, but the older ones would be way up there. Monty Python and the Holy Grail and The Princess Bride might make the list if they weren't too old. Back to the Future 1-2, but not 3. Ghostbusters. There'd be a lot of Alfred Hitchcock and Disney animation on my list if it went way-back.

Least-cool Oscar-nominated films: most of them that have won Best Picture over the past 20 years, except Braveheart, The Gladiator, and Return of the King. I especially dislike most of Quintin Tarantino's uncool rubbish-- neither entertaining, thought-proviking, cathartic, nor escapist; just vile, base, sick, predictable trash. Someone else's treasure, perhaps.

Edited to add...

Now that I've read everybody else's lists, I'm amazed I overlooked Jet Li, Jackie Chan, or Chow-Yun-Fat films. Too cool for me, I guess. Not a huge fan of Van Damm, Stalone, Bruce Willis, Clint Eastwood, Tom Cruise or Steven Segall; but Top Gun, The Last Samurai, Die Hard, Judge Dredd, Demolition Man, and a few others were very cool, though.

For a note of reference, Princess Bride just squeaks in, having been made in 1987. I thought it was older too, otherwise I'd have had it on my list as well.

I didn't include runners up, but should have: Here's some, a few inspired by other's suggestions. Some may be a smidge too old...

Bring It On
The Whole Nine Yards
Collateral
High School Musical
The Fast and the Furious
Men In Black

And now, for my nomination of the movie that did more to absolutely, totally, and completely screw up being cool, even though it tried mightily.

Torque

I have to start by acknowledging Undercover Brother and Austin Powers: International Man of Mystery simply for being so delightfully corny and self-mocking that I replayed both enough times to nearly recite every line.

The top ten nominations include:

One Flew Over the Cuckoo's Nest is two years out of range, but this thread is two years late!
Goodfellas
Reservoir Dogs
Saving Private Ryan
A Life Less Ordinary
The Silence of the Lambs
Fargo
Pulp Fiction
Kill Bill: Volume 2
Shrek (2001)
The Green Mile
The Shawshank Redemption
Dead Man Walking and
Trainspotting

P.S. I can't count.

Hmm, this is hard. So many good movies have come out in 20 years its almost not fair to list the 10 best/coolest. But here goes anyway...


In no particular order of course:

The Lord of the Rings
The Matrix (only the first one)
Fight Club
Pulp Fiction
Der Untergang (Downfall)
LA Confidential
Batman Begins
Gladiator
The Big Lebowski
Equilibrium

Honorable mentions include the following:
Die Hard, Pirates of the Caribbean, Snatch, Kill Bill, The Usual Suspects, Memento, Goodfellas, Sin City, Terminator 2, Full Metal Jacket, Groundhog Day, Battle Royale, Kung Fu Hustle, Man on Fire, Office Space, Strange Days, Dark City, Tears of the Sun, The Bourne Identity, The Fifth Element, Underworld, X-Men, The Descent, Event Horizon, The Sixth Sense plus a whole lot more I can't remember right now.

Just for fun I'll include my worst big budget movies list (in my opinion):

Batman & Robin
The Matrix Revolutions
Bloodrayne
Last Action Hero
Hudson Hawk
Alexander
The Whole Ten Yards
Oceans Twelve

In somewhat a particular order:

The Count of Monte Cristo(Remake and done very well, one of my favorites)
Desperado(Just down right sexy)
300(No wimps allowed)
Heat(No wimps allowed once again)
Underworld(Swoons for sexy vampiress)
Transporter(hard hitting unrealistic action)
Star Wars: Revenge of the Sith(Cause the Dark side is more fun)
Braveheart(like 300 this movie makes you want to fight for what is right)


more to come later

Hmm... coolest, eh? Well, my definition of cool is something that's a bit against convention, ploughing it's own furrow - something that, ultimately, doesn't really care whether anyone likes it. Definitively, then, I think cool movies are distinct from great ones, though there is a lot of overlap.

For example, Spartacus is cool, The Vikings is cool, but neither The Searchers or Ben Hur are remotely cool. However, of these four, only Spartacus and The Searchers are truly great. About the coolest film ever made would be Blade Runner, but it's a deeply flawed piece of film-making. Bambi is near-perfect film-making, but so uncool as to almost come back the other side into cool again.

Ten v. cool movies of the last two decades:
Die Hard*[[i]
[i]Sin City*
Serenity
Tombstone
Batman Begins
Miller's Crossing*
Pan's Labyrinth*
The Big Lebowski
Fargo*
Crash

Of these, only those marked with an asterisk would have a cat in hell's chance of making it into a list of great ones, though they are all very good, IMO.

Okay. Coolest. Not the best or most artistic but coolest movies of the last 20 years.

Fight Club
L.A. Confidential
The Usual Suspects
Pulp Fiction
Crash
American History X
Matrix
Memento
American Beauty
Spanglish

my apologies to the movies I would have picked had I thought of them.

and special note, Julian's nominee Pan's Labyrinth is a darn good movie.

pps. I can't believe I totally blanked on female lead movies. The Holiday, Erin Brockovich, Notting Hill occured to me, but didn;t pass the cool test.

Narrowing choices down to 10 is tough! What's cool to me might not be cool to the next person. Anywho, I went with:

The Usual Suspects
The Shawshank Redemption
Kiss Kiss Bang Bang
Frida
Basquiat
Being John Malkovich
V for Vendetta
Fargo
O Brother Where Art Thou?
American Beauty

The others I was considering were (and I'm sure I missed/forgot a bunch):

Se7en
The Green Mile
Pollock
Hotel Rwanda
Silence of the Lambs
The Black Stallion
Seabiscuit (yeah, so I’m a dork for horse movies)

P.S. Lesly, Cuckoo's Nest missed by more than 2 years - try 12. It definitely makes my "best movies of all time" list, though.

10 coolest movies .... let me think ...

# Lord of the Rings trilogy
# Die Hard I
# Terminator II
# Pulp Fiction
# Heat
# Fight Club
# The Matrix I
# Fear and Loathing in Las Vegas
# The Sixth Sense
# The Usual Suspects

Since we're going for cool and not necessarily great... here's my list.

In no particular order:

1. Se7en
2. The Matrix
3. Reservoir Dogs
4. Memento
5. Die Hard
6. Terminator 2: Judgement Day
7. The Bourne Identity
8. Akira
9. Trainspotting
10. The Lord of the Rings

1. LOTR trilogy
2. Aliens
3. Saving Private Ryan
4. The Shawshank Redemption
5. Tombstone
6. Blackhawk Down
7. Rounders
8. Silence of the Lambs
9. Terminator 2: Judgement Day
10. JFK

Oh, cool as in awesome. Let me try again. In no particular order:

Pulp Fiction
Kill Bill: Volume 2
Fight Club
Sin City
A Life Less Ordinary (really great rent)
Total Recall
Forrest Gump
Trainspotting
V for Vendetta
Fear and Loathing in Las Vegas

One of these is gonna get bumped to make room for Transformers soon baby!

These were some great ones.

American titles for some of these:

The City of Lost Children - Jeunet (fantastic film)
Amelie - Jeunet (also tres fantastique)
Brotherhood of the Wolf - Gans (I liked it... but not the coolest, in my book.)
The Professional - Besson (another fantastic film)

Donnie Darko actually pushes Trainspotting off my list.

I have so many favorite movies it would be impossible to list them all, I like movies that make you think the most. Comedies are good, as well as sci-fi and action movies as well. Here are my favorites of 4 different categories.

First the top 10 thinker movies, I don't know if thats actually a movie category but here they are, some are rather rare like "My dinner with Andre" but that one in particular is one of my favorite movies, extremely deep. A handful of these movies are a bit older than 20 years but all of them but 1 I believe are at least 80's to present day.

My Dinner With Andre
Pink Floyd The Wall
Buffalo 66
American History X
Another Day In Paradise
American Beauty
Cast Away
The Truman Show
The Ice Storm
Girl Interrupted

Top 10 Action films

Saving Private Ryan
Casino
Die Hard "sequels wernt bad either"
Pulp Fiction
Lethal Weapon
Air Force One
True Lies
Carlito's Way
Young Guns
Twister



Top 10 Sci-Fi films, actually I Thought of more than 10 for this category

Terminator, and all the sequals
The Matrix "also a deep thinkers movie"
King Kong (2005)
Deep Impact
Armageddon
Independence Day
Jurassic Park
Alien, and all its sequels
Predator
Total Recall
Stargate
War of the Worlds (2005)
Back To the Future
Hollow Man
Godzilla (1998) USA
Robocop and part 2


"West World", This movie is a bit older than 20 years but It was such a good movie I though id add it in and actually give a brief description of it. Its also less heard of and probably sounds like a Western but its actually a Sci-Fi and a Western. Its about a massive cooperation that takes probably 50 square miles of land and makes 3 tourist attractions that are supposed to be replicas of other times. I think they had Westworld, Romanworld, and Futureworld. In the movie you follow two characters that pay big bucks to visit their replica of the Old West. All three resorts were filled with Human like Androids "played by real people" that filled the roles of bar tenders, gun slingers, hoar's, you name it. Everything was set up to revolve around you to make the trip fun. The guys were given guns, and there were basically no rules to what you could do. The android gunslingers had guns as well, but were supposed to be programed to target only other Andriods, not people. It was supposed to be full proof, but similar to the movie Terminator the Androids became self aware and began thinking for themselves. Everything goes haywire, and a lot of people die while one of the gunslingers proceeds to chase the main character into the other resorts. Its a cool movie that Id love to see a remake of. Not too many people I know have seen it.

I could go on and on with all these categories, I'll do comedy and call it quits.

Top 10 Comedies

Space Balls
Naked Gun and the sequals
Airplane and part 2
Young Frankenstein
Napoleon Dynamite
Blazing Saddles
Happy Gilmore
Wayne's World
Dumb and Dumber
Shawn of The Dead
Groundhog Day
Office Space

Oops that was more like 12 for Comedy, its hard to do any of these categories justice without spending about 2 hours doing it, but overall I think one of the best movies of all time was Forrest Gump, I couldn't figure a category for it because it really has the best of about everything, Comedy, Romance, Action, History. Tom Hanks played what was probably his best role of all time, and I think this movie is truly unique in how it was played out.

VERY cool movie! I laughed my butt off. Have you heard about "Black Sheep" (zombie sheep in New Zealand)?

Yea Shawn of the dead was a hoot, I still laugh at that one. I took a look at a trailer to Black Sheep, sheep's as zombies is crazy stuff, looks like it could be funny. Violence of the lambs, lol.

Man, I love movies. I really do. I think I could survive in a 10x10 cell (with a big screen and a decent couch) for 10 years if all I to do was watch movies all day. I spent the better part of yesterday trying to think of 10 super cool movies <20 years old that other folks haven't listed yet. The longer I took the more difficult it was to do that. So I've broadened "coolness" a bit to mean a movie that #1 has a high rewatchability factor, #2 has particularly original style/mood or characters, and #3 may not be a very good movie in the strictest sense.

here's my list in no particular order

1) Live Aquatic with Steven Zissou

2) Kingpin

3) Oceans 11

4) The Untouchables

5) Bottle Rocket

6) The Lost Boys

7) Love Jones

8) Willow

9) Pitch Black

10) The Lost Boys

and as an added bonus, I've included my list of top 10 coolest movie characters of the last 20 years. The are almost in order. There are tons of super cool characters I hated to leave off of this list.

1) Jules- Samuel L. Jackson, Pulp Fiction
2) Doc Holiday- Val Kilmer, Tombstone
3) Carlito Brigante- Al Pacino, Carlito's Way
4) T100- Arnold, Terminator 2
5) Marv- Mickey Rourke, Sin City
6) Maximus- Russel Crowe, Gladiator
7) William Wallace- Mel Gibson, Braveheart
8) Tom Reagan- Gabriel Byrne, Miller's Crossing
9) Ethan Hunt- Tom Cruise, Mission Impossible Series
10) Leonidas- Gerard Butler, 300

Why did you put 'the Lost Boys' twice?

It must've been a doubly cool of a movie.

aww crud, I didn't mean to do that. Take off one of those Lost Boyses and put 25th Hour in its place. That ought to fix it.

I don't know that I'd include it on a "coolest 10" list, but I enjoyed The Lost Boys...especially Keifer Sutherland in all his 80's boyish (well, an evil boy) hottie-ness.

Ack...forgot 2 others. 10a. The Professional and 10b. American History X.

As so many of you have already said previously, we each may see "cool" differently. I see it is as unflappable under pressure, with witty comments.

This means that many of the Bond Films would make my list as would the following:

Undercover Blues
The Borne Identity
Oceans 11
Men in Black
The Princess Bride
Kiss of the Dragon
Oceans 13
The Three Musketeers (1993)(Just because I loved Oliver Platts version of Porthos)
Pirates of the Caribbean 1
The Mask

Most of these are comedies because I think the wisecracking, unflappable hero is cool. I would have loved to include Spiderman in this but unfortunately they decided to tone down the comedy side of him and focus more on the drama side. Darn it all. That was why my Spidey was my favorite superhero.

Here are my 10
1. Lord of the Rings
2. Blackhawk Down
3. The Matrix
4. Terminator 2
5. Braveheart
6. Shooter
7. Gladiator
9. the 300
10. Saving Private Ryan

While I, as always, bow to Wertz' superior cinematic knowledge, I'll toss in my 2p.

Memento
Pulp Fiction
El Mariachi
Traffic
The Bourne Identity
Do the Right Thing
Fargo
Lola Rennt / Run Lola Run
Die Hard
The Royal Tennenbaums
on edit - I forgot Rounders...looks like 11 on the top 10 list.
...

Clerks / Mallrats / Chasing Amy iftheywereonlyonemoviewouldbemynumber11 (12)
Office Space at #12ish (13)


Honorable mentions to True Romance, notably for that scene with Christopher Walken and Dennis Hopper. I very nearly included the Matador, with Pierce Brosnan... Oh, and Carlito's Way!

El Norte and Heathers (I love my dead gay son!) apparently both missed the cut at 23 or 24 years old...