Can't Take Our Eyes Off of Him: The 17 Cutest Photos of Heath Ledger from 10 Things I Hate About You

When He Smiled

“I burn, I pine, I perish.” New kid Cameron James may direct this line (lifted directly out of Shakespeare’s Taming of the Shrew, which inspired 10 Things I Hate About You) at the popular and selfish Bianca Stratford in the 1999 movie, but it’s an apt description of how the late Heath Ledger made us feel in his role as the tough “pretty boy” Patrick Verona.

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When He Negotiated a Deal with Joey

With his tousled hair and unapproachable air, Patrick made us want to become poets, too — it isn’t fair. Even as he agreed to narcissistic Joey Donner’s proposition to take out the equally unapproachable Kat Stratford for money, we couldn’t help but love him already.

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When He Agreed to Help Cameron

As Patrick, Ledger drilled a hole through Cameron’s textbook — and our hearts.

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When He Approached Kat

While Patrick’s bold first attempt to charm Kat was slightly over the top — “Well maybe you’re not afraid of me, but I’m sure you’ve thought about me naked, huh?” he asked — we couldn’t help but identify with her wry response: “I want you, I need you, oh baby, oh baby.”

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When He Got Book-Slapped

Perplexed and intrigued by Kat’s own personal brand of feminine mystique (and at first spurred on by his deal with Joey), Patrick persisted in trying to crack her code, trailing her through a bookstore only to be turned down once again.

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When He Played Pool in a Bar

Patrick called in backup to learn more about Kat’s interests in the form of Cameron and Michael, who masterminded the plan to get Kat a date in order for Cameron to take out her sister Bianca, who could only date when Kat did. The nerdy boys met him at the quintessential bad-boy hangout, a smoky biker bar.

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When He Saved Kat After Her Table Dance Fiasco

Who thinks putting a drunk and possibly concussed girl on a swingset is a good idea? We forgive Patrick for this questionable choice thanks to his gentlemanly manner of taking care of Kat, stroking her hair after she’s puked presumably on his shoes.

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When He Refused to Kiss Her

In a more responsible scene, Patrick resisted when a still-inebriated Kat tried to kiss him. She was rightfully hurt and mortified, but also — she had just thrown up in front him. And he was respecting her right to sober consent. Cut the guy some slack.

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When He Smiled, Again

Seriously, how can anyone resist this smile?!

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When He Sang ‘Can’t Take My Eyes Off You’

This scene was just too good to be true. Ledger cemented his status as an instant (though reluctant) heartthrob when he slid down a pole and serenaded Kat with the help of the marching band in front of the entire soccer team, forever redefining the expectations of teen girls everywhere when it comes to grand romantic gestures.

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When He Took Kat Paintballing

After Kat flashed her soccer coach to help Patrick escape from the detention he got for his musical stunt, the two went for a romantic paddle-boating ride before going paintballing in one of the most iconic first date scenes of all time.

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When He Threw Off His Goggles and Kissed Her

We don’t hate this first kiss — not even close, not even a little bit, not even at all.

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When He Opened Up

This swoon-worthy hair tuck is not talked about enough.

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When He Saw Her at Prom

Thankfully, Kat turned up at the prom, and we got to see Heath — er, Patrick — in a tux.

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When He Got Called Out

Naturally, Joey had to ruin everything, revealing the nature of his deal with Patrick. Thankfully, Bianca then punched him in the face — twice — and kneed him in the groin.

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When He Auditioned

10 Things director Gil Junger recently reflected on Ledger’s immediate appeal during his audition for what would become his breakthrough role.

“Heath walked in, and I thought to myself, if this guy can read, I’m going to cast him. There was an energy to him, a sexuality that was palpable,” Junger told the New York Times as part of an oral history ahead of the film’s 20th anniversary on March 31.

“The instant the door closed, I turned to the women in the room and said, ‘Ladies, I have never wanted to sleep with a man, but if I had to sleep with a man, that would be the man. Please cast him immediately,’ ” he said.