This site contains affiliate links to products. We may receive a commission for purchases made through these links. Learn more

The 30 Coolest Films Ever

Best viewed through sunglasses

The 30 Coolest Films Ever

To celebrate the commemoration of all things cool in this week's issue, we decided to trace the evolution of that tricky concept – cool – through the medium of cinema.

So, without further ado, we present for your fair delectation the 30 coolest films of all time.

Any we've missed? Let us know at the bottom?

(Images: Rex Features, All Star)


Year: 1942

Any film starring Humphrey Bogart is obviously dripping in cool – The Maltese Falcon, Key Largo, To Have and Have Not, The Big Sleep etc – but Casablanca is undoubtedly his finest moment. Strong, reserved, taciturn, cynical… his hard-boiled character Rick Blaine naturally commands respect. But besides his effortless interpretation of powerful masculinity – the snappy suits, his economical way with words – it’s his heroic nobility that cements Casablanca as a founding pillar of cinematic cool.

The Wild One

Year: 1953

“What are you rebelling against, Johnny?” The answer to those six simple words – “Whaddaya got?” – heralded the birth of the teenager and by extension the emergence of the sine qua non of 20th Century Cool: youth culture. Marlon Brando’s brooding leather-jacketed biker visually signalled a complete break with the old order and naturally appealed to members of the opposite sex. And there’s nowt cooler than that.

Rebel Without a Cause

Year: 1955

If The Wild One opened the door to a brave new world, Rebel Without A Cause stylishly sauntered in through that door and nothing would be the same again. James Dean’s iconic performance as the titular troubled teen Jim Stark sent shockwaves through Hollywood. The realism spoke to teenagers around the world, as men and women alike flocked to witness this authentic portrayal of malcontented youth. Dean’s death a month before the film’s release meant that the film was crystallised in the canon of cool for eternity.


Year: 1958

Some films are born cool; some have cool thrust upon them. Others, like Alfred Hitchcock’s defining masterpiece, Vertigo, acquire cool over time. The classic tale of obsession and our helplessness in the face of that fact, Vertigo might appear to have all the trappings of a psychological thriller, but it’s much more than that. Playing against type, James Stewart is superb as the retired police detective suffering from acrophobia hired to shadow the mysterious blonde Kim Novak. The depth and layers slowly reveal themselves over time, but then some things are worth waiting for.


Year: 1960

Call it continental chic, but come the dawn of the 60s all the hipsters were looking towards France for cool inspiration. The French New Wave, best exemplified by Jean-Luc Godard’s Breathless (A Bout De Souffle), captured the times perfectly. Here, Jean-Paul Belmondo – all beat generation cool and proto-mod style – etched himself into pop culture folklore thanks to his devil-may-care attitude and his natty dress sense.


Year: 1966

Everyone knows London was swinging in the 60s, and Blow-Up helped give the capital an extra couple of spins on the wheel of cool. A dark, often confusing tale of hip photographer Thomas (based on David Bailey), the abstract nature of Michelangelo Antonioni’s first English language film is offset by the unparalleled brilliance of David Hemmings as Thomas. His floppy fringe and post-mod wardrobe (have white jeans ever looked so alluring?) defined an age. Top soundtrack from Herbie Hancock too.


Year: 1968

If there’s nothing cooler than youthful exuberance and sticking two fingers up at authority then Lindsay Anderson’s controversial if.... is dining at the high table of cool. Chiming perfectly with the counterculture revolts of 1968, if.... tells the tale of an uprising at a conventional English public school. Malcolm McDowell is majestic as the subversive Mick Travis: a charming character brimming with infectious idealism.


Year: 1968

There might be many pretenders to the throne but there is only one King of Cool, and that, of course, is Steve McQueen. With his stylish, clean cut Ivy League-cum-mod apparel, McQueen reached a devilish crescendo in Bullitt. Yes, the iconic opening titles and that car chase help, but Bullitt has endured because of one reason, and that reason is Steve McQueen.

Easy Rider

Year: 1969

If Bullitt managed to meld conventionality – Steve McQueen’s character was a cop, albeit a maverick – with cool, Easy Rider made no apologies in embracing the late 60s counterculture. A psychedelic road movie starring Dennis Hopper, Peter Fonda and Jack Nicholson, its notion of attaining freedom and dropping out of society spoke to a generation.

A Clockwork Orange

Year: 1971

Stanley Kubrick’s spellbinding interpretation of Anthony Burgess’s dystopic novel would have made this list without the controversy that subsequently surrounded it. Not only did it vividly depict the unsavoury aspects of a society gone awry through the eyes of an ultra-violent gang led by Alex (Malcolm McDowell again), it invented new ways of speaking and dressing. The fact that you couldn’t watch it in this country for 27 years added to its mystique too.

Get Carter

Year: 1971

Get Carter is the British Bullitt to A Clockwork Orange’s Easy Rider. A brutal and uncompromising piece of cinema, redemption, of sorts, is found in the mesmeric performance of Michael Caine. Immaculately attired in his tailor friend Dougie Heyward’s suits – which harked back to the gangsters of the 30s – Caine was at the peak of his powers in Mike Hodges’s masterpiece. No end of quotable lines either.


Year: 1971

If one were to assemble a list of ingredients for a cool film it might read something like Shaft. Gangsters? Check. Copious use of leather? Oh yes. A stunning soundtrack? Step forward Mr Isaac Hayes. Popularisation of a new genre? Indeed, take a bow Blaxploitation films.

Mean Streets

Year: 1973

Martin Scorsese had made two films before Mean Streets, but with respect to both, neither Who’s That Knocking At My Door or Boxcar Bertha had quite the impact of his third motion picture. Starring Harvey Keitel and Robert De Niro (whose arrival onscreen has arguably never been bettered), and concerned with the now familiar Scorsese tropes of loyalty, guilt and redemption, it remains the quintessential rock’n’roll movie.


Year: 1979

The law of cool subsection 3.14 states that mods are cool. The music, the fashion and the attitude still speaks to those wanting to locate the essence of hipsterdom almost 50 years on. Although made a decade and a half after the mods’ initial heyday, Quadrophenia – loosely based on The Who’s rock opera of the same name – remains a reference point for those wanting to mix style and subversion.

American Gigolo

Year: 1980

Richard Gere gets paid to have sex with women; drives expensive cars; wears the latest threads and has all the latest gizmos in his fabulously decorated pad. What’s not cool about that? In all seriousness though, the powerful aesthetic developed in American Gigolo (formulated by designer Giorgio Armani) was to set a theme for the money-mad 80s.

Blade Runner

Year: 1982

It could be argued that Harrison Ford should feature on this list for his starring roles in the Star Wars and Indiana Jones franchises. His coolest film, however, is Ridley Scott’s Blade Runner. Not only did Blade Runner take sci-fi films out of the realm of the geek, it pre-dated the dystopic fin-de-siècle mood of the late 20th Century by a good 10 years. And just look at Ford’s Rick Deckard; has a burned-out cop ever look so fashionable?


Year: 1990

Outlaws are always cool. So while most people don’t actually want to be gangsters, watching them on the big screen is always a visceral thrill. And gangster movies don’t come more hip than Martin Scorsese’s Goodfellas. Everything about the two-and-a-half epic is perfectly judged – from the casting (De Niro, Ray Liotta, Joe Pesci, Paul Sorvino and Lorraine Bracco), the music (Rolling Stones, Donovan, Cream) to the wise-cracking criminals in their sharp suits. What’s cooler than cool? Goodfellas.


Year: 1992

In many respects grunge was the ultimate anti-cool youth cultural movement. It was scruffy, wild and paid scant regard to previous arbiters of cool like the beats, the mods and co. This, of course, made it supremely cool for teens and those drifting 20-somethings, termed Generation X by Douglas Coupland, in the early 90s. Singles was the definitive grunge movie, capturing the ennui of the age perfectly. That it starred Matt Dillon (always cool) only enhanced its hip credentials.

Reservoir Dogs

Year: 1992

Unless you were there, it’s difficult to envisage just how uncool suits were in the early 90s. Firstly acid house had heralded a freer, more relaxed mode of dress among the youth of the late 80s, and then the aforementioned grunge kids came along and were just content to raid the local thrift stores for sartorial (in)elegance. Quentin Tarantino’s Reservoir Dogs gave suits a much needed shot in the arm. Combining a magpie’s eye for pop culture with snappy dialogue and a suite of fully formed characters, Reservoir Dogs set a new benchmark for alternative cinema.

Dazed & Confused

Year: 1993

As a kid you never believe it when your parents tell you that your school days are the best years of your life. Richard Linklater’s affectionate hymn to his mid-70s school days in Texas, demonstrates that, for once, the old folks were right. At turns hilarious and bittersweet, it ideally captures that carefree spirit of post-adolescence, when doing the cool thing is a full time job. Arguably the best high school movie ever made.

Pulp Fiction

Year: 1994

If Reservoir Dogs suggested Quentin Tarantino was a man of considerable talent, Pulp Fiction demonstrated that the carefree director was no one-trick pony and was, in fact, fully conversant in the lexicon of cool. Drenched in the language of postmodernity – ironic, high pastiche, humorous – Pulp Fiction not only revitalised the career of John Travolta (a former champion of hip), it made bona fide stars of Uma Thurman and Samuel L Jackson. Terrific cameos from Bruce Willis, Christopher Walken, Tim Roth and Harvey Keitel too.


Year: 1996

Trainspotting could hardly fail. Its source material, Irvine Welsh’s acclaimed novel, was the most caustic book of its time; the actors involved – Ewan McGregor, Robert Carlyle, Jonny Lee Miller – were fresh, dynamic, luminous; and the spirit of the film chimed with the iconoclastic spirit of Britpop (well, the first seeds of Britpop anyway). A great soundtrack and aesthetic – evoking the casual culture of the 80s – ensured Trainspotting was the coolest UK film of the 90s. It hasn’t been bettered since.

The Big Lebowski

Year: 1998

Jeff Lebowski was not hip; his demeanour suggested on overgrown slacker; he was unemployed with seemingly little or no prospects. However, he was The Dude, and for this he was cool. In a career littered with cult classics (Raising Arizona, Barton Fink, Miller’s Crossing, Fargo…), The Big Lebowski is the Coen Brothers' masterpiece. Since its 1998 debut the film has taken on a life of its own (how many films have a religion in its honour?) and it continues to speak to our confusing times. A case of enduring cool.

Out Of Sight

Year: 1998

Much like Trainspotting, Out Of Sight had fortunate beginnings. In this case an Elmore Leonard novel. However, without the presence of one George Clooney, Out Of Sight could have been merely good. Imbued with an unquenchable thirst for life and adventure, and possessed of a cocksure attitude, Clooney’s Jack Foley is one of the coolest characters on celluloid. His hotel bar confrontation with Jennifer Lopez is worth of cool status alone.


Year: 1998

Filmmaker Wes Anderson is cool. His films – from Bottle Rocket through The Royal Tenenbaums to Fantastic Mr Fox – reflect his eccentric and unique vision. His second film, Rushmore, is perhaps his most quintessential. It awoke the world to the idiosyncratic talents of Jason Schwartzman, and helped revitalize the career of cool icon Bill Murray. A tale of youthful (and middle-aged) rebellion, Rushmore speaks up for strange outsiders everywhere.

Fight Club

Year: 1999

Cool films not only capture a time and place; they are, at heart, timeless. Fight Club is one such film. Again, it appears it could hardly fail. Adapted from Chuck Palahniuk’s lauded book by David (Se7en) Fincher, and starring Brad Pitt and Edward Norton, it had high expectations. It effortlessly met them. Encapsulating the disillusionment at the heart of many young men at the end of the 20th Century, Fight Club’s themes remain relevant to this day. And who, when confronted with a dilemma, hasn’t asked: What would Tyler Durden do?

Ocean's Eleven

Year: 2001

A remake of the 1960 Rat Pack vehicle and starring George Clooney, Brad Pitt, Matt Damon, Don Cheadle, Andy Garcia, Casey Affleck, Elliot Gould and Julia Roberts (as the sophisticated eye candy), Ocean’s Eleven wore its cool credo as a badge of honour. A heist movie set in a Las Vegas casino that combined male camaraderie and stylish action, Ocean’s Eleven is an unapologetic alpha male film.

This Is England

Year: 2006

Shane Meadows doesn’t make conventionally cool films: the likes of Twenty Four Seven, Dead Man’s Shoes and A Room For Romeo Brass are gritty and at times uncomfortable viewing. This is what makes them cool of course. They operate outside the often times glamorous world of cinema. Taking this on board, This Is England is Meadows’s coolest work. Evoking the skinheads of his early 80s youth, the film’s hard-hitting tale is enough to warrant cool status, but when you factor in the skinhead fashions and music, the cool quotient is unmistakeable.


Year: 2007

A dead rock star is a cool rock star. A misunderstood poetic rock star who died by his own hands is a very cool rock star indeed. The mystique of Ian Curtis had grown steadily since his suicide in 1980, but Anton Corbijn’s stylish movie elevated Curtis and his band Joy Division to new heights. Shot in black and white and announcing a major new talent in Sam Riley, Control was naturally cool.


Year: 2011

Every now and again actors come along who grab the spirit of the times by the short and curlies. With Drive, Ryan Gosling has done just that. Loved by critics and cinemagoers alike, the film concerns itself with themes of freedom and outsiders and touches upon perennially cool genres like B-movies and film noir. As the titular getaway driver, Gosling is the ultimate uncommunicative anti-hero evoking the likes of Steve McQueen, Lee Marvin and Clint Eastwood. Drive was easily the coolest film of 2011.