5. 10 Things I Hate About You
The most epic chick flick of my time. And by my time I mean was essentially my generations Sixteen Candles. I watched, and still watch, this movie endlessly. This film did exactly what Clueless did. It borrowed from the best. It's based on Shakespeare's
The Taming of the Shrew which, like many of Shakespeare's romantic comedies, was an interweaving tale of characters who were all having their own type of mishaps in love. But most importantly, this movie was responsible for breaking out Heath Ledger and Julia Stiles. (Joseph Gordon-Levitt, who is always great, didn't explode quite a much. As we all know, it's been a gradual and well deserved rise to fame for him.) But when Ledger hit the screen, it was like, "Whoah. Who is this guy?" He had strong screen presence, was handsome, and a bit of the bad boy. Who better to "tame the shrew", who just so happened to be equally tough and gorgeous in her own right. Julia Stiles was funny, smart, and strong. She's the kind of girl you don't approach because you're afraid she'll beat you up, but there's something about her that you're desperate to find out. The film is so well done that I think most people were surprised at its wild success. The script is solid, the performances are top notch, and Gil Junger's directorial debut proved his greatest. (Seriously Gil, get it together and come on back bro.) Because of the wonderful chemistry each of these characters (and actors for that matter) share, the film shares common ground with Clueless in that it elevated the genre from from boy meets girl, lets fall in love, the end. And took the audience on a Shakespearean comedy of errors and screwball antics much like the old Clark Gable rom-coms of the same genre. It's an honest, old school love story that works for everyone.