A decade ago this past summer, Kay Hanley and her bandmates in Letters to Cleo had to be talked into accepting a free trip to Hollywood when the producers of a new teen comedy approached them about contributing to the film’s soundtrack. Little did the band know that within a couple of weeks they would be planted high on a rooftop in Tacoma, Washington, fearing for their lives as a helicopter buzzed closer … and closer … and closer …

First things first. Next March will mark ten years since the theatrical release of 10 Things I Hate About You, a comedic update of Shakespeare’s The Taming of the Shrew that has overcome a middling performance at the box office to become one of the most popular teen movies of the post-John Hughes era. The film is best remembered these days as the American acting debut of Heath Ledger – who, ironically, is almost certain to be vying for a posthumous Oscar just a couple weeks before the anniversary of that debut. It’s likely Ledger’s participation, as much as the film’s immense likeability, that accounts for its near-constant presence on pay and basic cable over the past decade.

But 10 Things was much more than a showcase for Ledger and Julia Stiles, the co-star who also used the film as a springboard to greater fame and fortune. For all the contrivances of its Shakespearean plot, the film is among the most sensible and believable of the teen genre, full of warm and funny performances from a terrific supporting cast. Grown-ups Larry Miller and Alison Janney get some of the best moments, happily – particularly Miller as an Ob-Gyn so paranoid about his daughters dating that he forces them to “wear the [empathy] belly around the living room” before they leave the house. “Kissing? That’s what you think happens [at the prom]? I’ve got news for you. Kissing isn’t what keeps me up to my elbows in placenta all day long.”

The icing on this cupcake of a film is its music – a panoply of late-’90s modern rock (Semisonic, Sister Hazel, the Cardigans) and ’80s funk and pop (“Atomic Dog,” “Dazz,” “Push It”). Ledger’s most indelible scene featured him high-stepping across the football-stadium bleachers as he serenaded Stiles with “Can’t Take My Eyes Off of You” – with an unexpected assist from the marching band. (more…)