The Big Lebowski (1998)
Jeff Bridges as The Dude—or "his Dudeness, or Duder, or El Duderino if you're not into the whole brevity thing"—is one of the most inimitable characters in movie history. After a case of mistaken identity, the lovable deadbeat finds himself in a series of strange, precarious situations, in what co-director Joel Coen describes as "a hopelessly complex plot that's ultimately unimportant".
Generous with its oddball characters and one-liners, The Big Lebowski always manages to scratch an itch we didn't even know we had.
Dazed & Confused (1993)
It may have been a box office flop when it first came out, but Dazed and Confused has gone on to become a cult hero that launched the careers of some of its now-all-star cast, including Milla Jovovich, Ben Affleck, Parker Posey, Matthew McConaughey and Anthony Rapp.
A love letter to the fast cars and feathered hair of the '70s, it follows a riff-raff group of stoners, jocks and geeks to produce what Rolling Stone described as "one of the single most spot-on movies ever made about the lazy, hazy days of American youth".
Ugh, as if we weren't going to include Cher and the gang on this list. It's the movie that had a generation dancing to Coolio's Rollin' With the Homies and dreaming of automatic closets; it introduced us to what it meant to refer to someone as a "Monet" and perhaps the most gut-punching insult you could hurl at a high school student teetering on that awkward line between clueless teenager and functioning adult: "you're a virgin, who can't drive".
Despite being centred around a group of rich kids in Beverly Hills, Clueless is a timelessly relatable classic that never goes out of style—much like its iconic tartan ensembles.
American Psycho (2000)
In this tale of monsters and men—or what turns men into monsters—investment banker Patrick Bateman is drunk on success but crippled by a more-than-fragile ego. During the day, he leads a lavish life that's envied by many but that barely (if at all) satisfies the jaded protagonist, played by Christian Bale. By night, the audience sees his mental decline as he finds a sense of power and control in death, destruction and delusion.
It's a dark, satirical perspective on the rat race, and a reminder of the price some end up paying for their shallow pursuits.
The Truman Show (1998)
Jim Carrey serves up a fantastic performance as Truman Burbank, an unsuspecting insurance salesman who happens to be the star in a reality show (before reality shows were even a thing, it's worth noting) watched by millions around the world.
The themes in this thought-provoking cult classic are perhaps more relevant now than ever, touching on the ethics of privacy, digital surveillance, society's voyeuristic obsession with reality television.
American Beauty (1999)
A satirical portrayal of suburbia, American Beauty tells the tale of a cast of characters all looking for ways to escape their mundane realities. Lester, played by Kevin Spacey, falls in love with his daughter's school friend and begins to fantasise about scenes of her shrouded in rose petals. His wife, Carolyn, has an affair with a sleazy local real estate agent. Their daughter, Jane, begins a relationship with their tortured artist-type neighbour, Ricky. Their stories all intertwine, and it's all one big happy mess.
At the 2000 Academy Awards, American Beauty won five Oscars including Best Film and Best Director for Sam Mendes.
An 86-carat diamond has a bunch of amateur crooks—including characters played by Jason Statham, Brad Pitt and Benicio del Toro—chasing after it. In true Guy Ritchie fashion, there are plenty of freeze frames, witty dialogue (even when it's borderline inaudible...you like dags?) and bareknuckle brute.
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A Clockwork Orange (1971)
Stanley Kubrick's audacious film adaptation of Anthony Burgess's 1962 novel is not for the faint of heart. Dark, dystopian and disturbing, A Clockwork Orange follows Alex DeLarge and his "droogs" on an evening of "ultra-violence". Alex is arrested and eventually agrees to be a test subject for a new aversion therapy known as the Ludovico technique, where his eyes are pried open as he's forced to watch sadistic scenes ominously set to music by his favourite composer, Beethoven.
Despite the attempt to redeem himself, the movie itself offers little redemption—in the end, it only leaves its audience questioning how we as a society respond to our shadows.