10 Things I Hate About You: A relic of my high school era, this movie is awesome for so many reasons. Not only is it a re-telling of Shakspeare's 'Taming of the Shrew', it stars actors who went on to become stars in Hollywood (Heath Ledger, Joseph Goden -Levitt), and who actually look like they're in high school. Better yet, the dialogue and pacing still comes off as witty over 10 years later. This is 'The Breakfast Club' of my age.
FUN FACT: This was improvised. The building was meant to explode and come down in one go and the crew had one take to get it right. When the explosions malfunctioned, Ledger reacted in character, and Nolan urged his crew to keep filming. By pure chance, it resulted in one of the greatest moments in the movie, and a moment that perfectly showcased Joker's archaic nature and Ledger's sheer talent.