20 Films That Prove 1999 Was The Best Year

20 films that prove 1999 was the best year to be a teenager in a movie theatre.

1. 1. Fight Club

A 35 year old Brad, need I say more?

4. 2. 10 Things I Hate About You

If you had this on DVD you were the coolest

If she didn’t make you want to stand up for what you believe in, I don’t know what type of person you are

6. 3. Big Daddy

The quintessential Adam Sandler film, which also sparked Dylan & Cole Sprouse’s Dual Star careers

8. 4. American Pie

This classic IMDB description gives it all away: “Four teenage boys enter a pact to lose their virginity by prom night.”

The start of a hilarious set of movies grossing over $900 million

10. 5. Star Wars: Episode I

The first episode of Star Wars was finally released

Jar Jar Binks nullified all that was good in 1999 and Ewan McGregor kicked some ass

12. 6. Runaway Bride

We were still in that hardcore Julia Robert’s era

14. 7. Never Been Kissed

Truly the cutest girl-gets-the-boy story

Poor Josie Grosie

16. 8. The Matrix

Neo, sooner or later you’re going to realize just as I did that there’s a difference between knowing the path and walking the path.

18. 9. The Green Mile

The Green Mile was nominated for four Academy Awards. Best Performance by an Actor in a Supporting Role, Best Sound Mixing, Best Adapted Screenplay and Best Picture.

20. 10. American Beauty

Did you know Green Mile lost the Academy Award for Best Picture to American Beauty?

Such a dramatic and poetic film. Also we finally realized that Kevin Spacey is good at creepy

22. 11. Cruel Intentions

The film that led to Reese Witherspoon and Ryan Phillippe’s intense real life relationship. No wonder there was so much chemistry on screen

Sarah Michelle Gellar played the perfect coke addicted, high school girl

24. 12. Toy Story 2

The second film in the most anticipated animated series

Tom Hanks and Tim Allen formed the most incredible duo

26. 14. The Sixth Sense

Terrifying kids around the world since 1999

Possibly the most iconic film quote of the year

28. 15. Girl, Interrupted

Did you know that Girl, Interrupted is based on a true story? Author Susanna Kaysen wrote the book based on her time in a mental hospital

24 year old Angeline Jolie Voight won an Academy Award for Best Actress in a Supporting Role

30. 16. Office Space

You would never know from the movie poster that Jennifer Aniston is a supporting character

This film also spawned the era of red staplers and jump-to-conclusion mats

32. 17. She’s All That

Minus the clothing, this movie has stood the test of time. It features the classic makeover scene, the boy falls in love with girl scenario and the nerdy girl wins the day

Academy Award winner Anna Paquin also makes an appearance as Freddie Prinze Jr.’s little sis

34. 18. Superstar

SNL Alums Molly Shannon and Will Ferrel took this Saturday Night skit and made it into a cult comedy

Mary Katherine Gallagher everybody.

This one deserves two gifs

37. 19. Notting Hill

Another Julia Roberts film

Nothing more needs to be said

39. 20. Austin Powers: The Spy Who Shagged Me

Another SNL character. The film grossed over $300 million in 1999!

Playing two characters at once - imagine the possibilities!

42. Clearly 1999 was the best year in film

Oh! And Britney Spears released Baby One More Time, Christina Aguilera debuted her first self-titled album, and Millennium by the Backstreet Boys was released.

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