Jesus of Cool: Ten Years of Loving “10 Things I Hate About You”

Written by Jesus of Cool, Music

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.

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Director Gil Junger even decided to give some screen time to a pair of bands appearing on the soundtrack: Save Ferris and Letters to Cleo. “Ralph Sall was the music supervisor on the film, and he had called us to see if we would come to L.A. to do a couple songs,” Hanley recalls. “I thought it was going to be horrible, but we agreed to go there and stay in a hotel for a week – obviously, it was like, ‘Duh, sure we’ll sing “I Want You To Want Me” for you.’

“But then [Junger] asked Ralph if he knew a band who could appear in the film, and the next thing we knew we went from doing our songs in L.A. to jetting up to do our scenes in Seattle. It was all very glamorous for a little band from Boston.”

Letters to Cleo first filmed a nightclub scene, singing an unreleased song called “Come On,” and then a prom scene along with Save Ferris in which Hanley sings Nick Lowe’s “Cruel to Be Kind.”

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Finally it was time to shoot the film’s closing-credits sequence. “They took us out to Tacoma, to [Stadium High School] where they shot the exteriors,” Hanley says. (The building was designed during the 1890s to resemble a French chateau, and was originally intended to be a luxury hotel before being renovated into a school.) “We didn’t know what we were supposed to be doing, only that we were doing ‘I Want You to Want Me.’ So they told us we were going up to the roof, and we thought, ‘OK, fine.’ But then suddenly we reach the top floor and have to climb a ladder to get to the attic, and we were like, ‘Where the fuck are we going?’

“And then they directed us up this structure that was like a fire escape – at best – and then through a trap door at the top. And this [production assistant] pulls me up and we see where we are, and we’re like, ‘Fuck, no!’ That roof was maybe the size of my kitchen – and with all of our equipment set up it seemed even more cramped than that – and the whole thing was protected by this little strand of something like chicken wire. And the wind was blowing like crazy, and we were like, ‘Holy crap!’

“So they told us, ‘This is a helicopter shot, and it costs $500,000 every time the helicopter has to take off, so don’t fuck this up!’ So we’re standing there, and we’re already barely able to stay upright because the wind is howling around us. And they hit the playback, and as we started playing we saw the helicopter appear, off in the distance. It’s hard to say how far away it was at first, because we were so high up in the air – but then all of a sudden the helicopter does this dive bomb directly toward us!

“At that point we were completely shitting our pants. Is the helicopter out of control? Is it supposed to be coming at us like this? And I’m thinking, ‘Don’t fuck up, keep singing the song, don’t fuck up, it costs 500 grand every time the copter takes off.’ And the thing circles us a few times and then moves away, and we’re thinking it’s over, but then it comes back. We were trying to stay professional, you know, but we kept glancing at each other like, ‘Could this be any more terrifying?’

“It was unbelievably scary — but it turned out to be such an amazing shot.” (The song begins at about the 1:30 mark in the following clip, the helicopter shot about 20 seconds after that.)

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Letters to Cleo’s rendition of “I Want You to Want Me” brought the group perhaps its greatest notoriety … though not enough to prevent it from splitting up a year later. To mark the band’s current reunion tour, a new rarities album titled When Did We Do That? was released on the band’s website, featuring “Come On,” “Cruel To Be Kind” and “I Want You To Want Me.”

Meanwhile, as 10 Things I Hate About You continues its endless run on cable TV – and movie fans everywhere continue to mourn the loss of Ledger – the basic-cable channel ABC Family last month greenlit a pilot for a 10 Things spinoff series. Junger, the film’s director, will oversee the TV pilot as well; presumably there will be no helicopter shots.

Letters to Cleo – I Want You to Want Me (download)
Letters to Cleo – Cruel to Be Kind (download)
Letters to Cleo – Come On (download)
Semisonic – FNT (download)

Purchase the DVD of 10 Things I Hate About You, or its soundtrack, from Amazon. Purchase When Did We Do That? from the Letters to Cleo website.