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20 Years Since One Of The Best Years Hollywood Ever Had

Some years are annotated by cinematic gems that make us hold the year up so the brilliance doesn’t end; movies that cross the spectrum and give us joy, tragedy, heartache, chills, motivation, and ultimately a reason to believe in the arts. Here are 19 movies that turn 20 in 1999, each movie giving us so much inspiration!

1. Fight Club

Helmed by David Fincher, and with a star-cast of Brad Pitt, Edward Norton, and Helena Bonham Carter. The movie looks at understanding a life that you planned, as opposed to the life that happened to you.

2. The Blair Witch Project

Heather Donahue starrer, this cult classic scared us so subtly that we aren’t sure if there is no subliminal  fright left within our souls. This movie is truly one of the most terrifying movies of all time.

3. Being John Malkovich

This comedy starring John Cusack and Cameron Diaz, is actually all about dark desires, missed connections, and surrealism!

4. The Mummy

Brendan Fraser and Rachel Weisz star in probably one of the most well known action-supernatural movies in the recent times. It has got excavation horror like you never knew could exist!

5. 10 Things I Hate About You

Julia Stiles, Heath Ledger, Joseph Gordon Levitt, and Larisa Oleynik star in this brilliant movie that is such an intelligent coming-of-age movie we truly feel it is not only for your teenybopper dreams, but for you to watch as an adult to know exactly why you don’t need to adhere to norms!

6. The Talented Mr. Ripley

Oh, Mr. Ripley – this Matt Damon, Jude Law, and Gwyneth Paltrow starrer is a classic case of an archaic version of catfishing but so sinister that the moment we saw it we ceased to trust people. Period.

7. Sixth Sense

This movie gave us one of the most iconic dialogues of our time – I See Dead People. Spoken by the cutest Haley Joel Osment in the most scary of all circumstances, cinematically, and we all were as curious as Bruce Willis, but possibly far more scared!

8. American Beauty

This movie was such an elegant foray into perversion, we tell you! Kevin Spacey held this one on his own with a bevy of a superstar supporting cast.

9. Girl, Interrupted

Winona Ryder and Angelina Jolie star in this absolutely mind-altering crazy movie that looks at mental disorders in such a real and authentic way, it hit too close to home!

10. Stuart Little

The most adorable, least gross mouse ever! Stuart Little literally warmed our hearts with his little mischief and concern and absolutely little cute Converse shoes – oh my God!

11. The Virgin Suicides

Sophia Coppola’s debut movie was a force of nature, it was so real in it’s manifestation of teen angst and parental control sprinkled with the aftereffects of tradition that are rooted in stereotypes.

12. Boys Don’t Cry

Oh that tragic tale of this movie. It really hit us in the feels, and Hillary Swank was so convincing that it was impossible to feel anything but gnawing empathy and sympathy.

13. Notting Hill

Julia Roberts and Hugh Grant star in the most OG of all romantic comedies ever. The story is so completely like nothing we would ever accept in real life, and that just made it all the more endearing!

14. Never Been Kissed

Drew Barrymore as the delightful, naive, gorkilicious undercover Josie, is a must-watch for all of us who battle between their alter-egos and their own vulnerable selves.

15. Cruel Intentions

We mean, let’s be real, this movie gave so many of us Bittersweet Symphony, and an absolutely torrid and incestuous love affair between Ryan Phillippe’s Sebastian and Sarah Michelle Gellar’s Kathryn with the naivete of Reese Witherspoon’s Annette. This movie was terrifically coy, smart, and voyeuristic!

16. The Green Mile

Tom Hanks and Michael Clarke Duncan in such fine roles that we can’t imagine a reboot of this movie with anyone else. The tragic and supernatural tale had us shivering so hard!

18. Matrix

Oh what a classic this one was! None of its further franchises could match-up to the art deco, avant garde, industrial chic magic of this movie! And the background score, my God!

19. American Pie

Well, ok, this one is an honourable mention because this may not be a cinematic brilliance, but was it a cult favourite. An ensemble cast of a brat pack fit for the burgeoning Y2K, this movie was so slapstick we couldn’t help but shake our heads in both curiosity, disgust, and a little bit of laughter.

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