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

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When He Smiled

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“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

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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

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

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When He Approached Kat

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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

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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

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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

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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

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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

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Seriously, how can anyone resist this smile?!

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When He Sang 'Can't Take My Eyes Off You'

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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

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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

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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

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

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When He Saw Her at Prom

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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

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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

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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.

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When He Melted Our Hearts

Twenty years later, we still can’t take our eyes off of this movie.

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

1 of 17

When He Smiled

1 of 17

2 of 17

When He Negotiated a Deal with Joey

2 of 17

3 of 17

When He Agreed to Help Cameron

3 of 17

4 of 17

When He Approached Kat

4 of 17

5 of 17

When He Got Book-Slapped

5 of 17

6 of 17

When He Played Pool in a Bar

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7 of 17

When He Saved Kat After Her Table Dance Fiasco

7 of 17

8 of 17

When He Refused to Kiss Her

8 of 17

9 of 17

When He Smiled, Again

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10 of 17

When He Sang 'Can't Take My Eyes Off You'

10 of 17

11 of 17

When He Took Kat Paintballing

11 of 17

12 of 17

When He Threw Off His Goggles and Kissed Her

12 of 17

13 of 17

When He Opened Up

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14 of 17

When He Saw Her at Prom

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15 of 17

When He Got Called Out

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16 of 17

When He Auditioned

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17 of 17

When He Melted Our Hearts

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