10 Things I Hate About You: The enduring charm of Heath Ledger in a romcom that still sings, 27 years on

Nostalgia is a wound that's also a balm, and it stings either way.

We keep searching for the past in the present, and get disappointed that the past insists on staying where it is. So when the present offers us a glimmer of the days gone by, we clutch at it, relive it, and blame the present for never being what the past was.

I had similar sentiments on October 20, when Julia Stiles took to the floor on Dancing with the Stars for the show's Dedication Night and gave her dance to Heath Ledger. With her partner Ezra Sosa, she performed a contemporary routine to Frankie Valli's Can't Take My Eyes Off You, the song Ledger's Patrick Verona sang to her Kat Stratford in the 1999 film 10 Things I Hate About You.

As a photograph of the two of them appeared on screen, Stiles laid a red rose on the stairs. Then came the surprise: Joseph Gordon-Levitt, Larisa Oleynik, Gabrielle Union, Andrew Keegan and Susan May Pratt walked out to join her, a class reunion staged in a ballroom. The judges gave her 36 out of 40. The tearful millennials gave her considerably more.

Ledger died in January 2008, at 28. Eighteen years on, he still has a way of filling rooms he isn't in. You find him in his 20+ films, in old interviews and you hear him in Can't Take My Eyes off You.

Almost immediately after the performance, the algorithm got to work. Clips flooded our timelines: the bleachers, the paintball fight, the prom. They brought back the giddy world of the late-90s teen romcom, and with it a bitter realisation: However much we might want it, we will never see Ledger in a romantic comedy again.

If his Joker in The Dark Knight, the role that won him a posthumous Oscar, set one bar impossibly high, his Patrick set another in an entirely different key: the Australian-accented bad boy, rumoured to have eaten a live duck, who wins the girl’s heart by serenading her in front of the whole school. In the process, he wrote the playbook on making a fool of yourself for love. Take note, gentlemen.

The film is a deft, palatable reworking of Shakespeare's The Taming of the Shrew, among his most contested plays, in which Petruchio of Verona marries the fiery Katherina of Padua and sets about 'taming" her' into obedience. Screenwriters Karen McCullah and Kirsten Smith kept the bones (the names, the Padua setting, the two sisters, the rule that the younger can't be courted until the elder is) and threw out the misogyny. Padua is now a Seattle-area high school; Petruchio of Verona becomes Patrick Verona; and the only taming that happens is mutual.

The Stratford sisters, Kat (Stiles) and Bianca (Oleynik), are bound by a rule laid down by their obstetrician father: Bianca can date only when Kat does. Since Kat has no interest in anyone at Padua High, Bianca is stuck. And so, there's Cameron (Gordon-Levitt), the new gawky teen who falls for Bianca at first sight. With his friend Michael, he hatches a scheme: persuade Joey Donner (Keegan), the school's preening, self-regarding model, who also has designs on Bianca, to pay Patrick to take Kat out. If Kat dates, Bianca is free.

Patrick, of course, falls for Kat, despite every withering rejection she throws at him. You know where it's going. You can predict the rupture in the final 20 minutes, and you are more than ready for the reconciliation. Predictability was never the point in such films. It mattered how you got there.

And 10 Things gets you there with real style: its toxic boys get their comeuppance from the girls (Bianca's prom-night punches at Joey remain deeply satisfying), and its soundtrack works as a character in its own right.

Listen closely and you notice something: for a film so emphatically of 1999, almost none of its defining musical moments are from 1999.

The film opens with Kat's car pulling up to school blasting Joan Jett's Bad Reputation, a 1980 punk snarl that introduces her before she says a word. It's a mission statement, and a lineage: Jett is the godmother of the riot grrrl movement that a girl like Kat would have worshipped in the late 90s. Kat is impervious to others opinions of her, and the film tells us so in under three minutes of guitar.

Then there's the bleachers scene. Patrick, trailed by the school marching band and dodging security, sings Can't Take My Eyes Off You, a 1967 crooner's ballad from Kat's parents' generation. It's a profoundly uncool choice, and that's the beauty of it.

Kat's entire persona is armour against looking foolish and playing to expectations; Patrick wins her by doing the thing she would never do, making himself ridiculous in public.

At the prom, my personal favourite: the ska band Save Ferris backing Kay Hanley of Letters to Cleo on Nick Lowe's 1979 power-pop hit Cruel to Be Kind". It is gloriously, unmistakably 90s, and it still makes me smile. But it's also the film winking at itself. That very night the truth about the bet comes out, and Patrick's kindness is revealed to have been bought. Cruelty and kindness, tangled together, set to a song you can dance to.

And for the finale, Letters to Cleo play Cheap Trick's "I Want You to Want Me" on the school roof (Tacoma's Stadium High, in real life). After two hours of characters pretending not to want each other, the film closes on the plainest possible statement of desire.

The pattern is the point. A late-90s film voiced its romance through 60s and 70s songs, refracted through 90s alt-rock covers, all laid over a story from the 1590s. 10 Things I Hate About You was already an act of nostalgia. It was always reaching back.

The film is full of small, specific pleasures, which is perhaps why it has become a cult phenomenon. Stiles's deadpan one-liners still have more zing than half the romcoms made today, from her classroom takedowns of the boys in her English class to her steady refusal to be impressed by anyone. Ledger, meanwhile, has enough charm to power a car, if charm could do that sort of thing.

One scene explains the film's following better than any other. After the prom fallout, Kat stands in Mr Morgan's English class and reads the poem she has written for the assignment, a list of the things she hates about Patrick. It begins as a list of grievances: his hair, his combat boots, the way he drives her car. It ends in collapse, with Kat admitting that what she hates most is that she doesn't hate him, not even close. Her voice cracks; she leaves the room in tears; Patrick watches, heartbroken.

Then comes the ending. Kat finds a guitar, a Fender Strat, in her car. Patrick admits he bought it with the money Joey paid him, turning the cash that started the deception into a gift for the girl who would rather make noise than make nice. When Kat warns him he can't buy her an instrument every time he messes up, he says, in the most Patrick way possible, that there's always drums, or bass, or maybe one day a tambourine. He is in it for the long game.

And that, brings us back to that ballroom, and to the ache of nostalgia that sometimes burn.

It is tempting to watch Stiles's tribute and conclude that the present is simply lesser: that they don't make romcoms like that any more, that we lost something we can't recover. Some of that is true. We will never get another Ledger romcom, and that loss is visceral. Yet one three-minute dance was enough to send millions of us straight back to the bleachers.

We can't go back to Padua. But we never really left. Not even a little bit.