Cracked olive-green leather pants. That’s what director Gil Junger vividly remembers about Heath Ledger’s first day on the set of “10 Things I Hate About You.”
“A white worn-out leather belt, some crazy pair of white shoes, a hat and who knows what shirt,” Junger continued, listing the various elements of Ledger’s Day One ensemble. “I looked at him and thought to myself, ‘If I put on any one of those pieces of clothing, everybody around me would burst out laughing.’ But for whatever fucking reason, on Heath it was so cool. He could sell anything.”
Junger was captivated by Ledger as soon as he met the then-18-year-old actor at his “10 Things” audition. The filmmaker, along with his team of casting directors — including Gail Goldberg, Donna Morong and Marcia Ross — were having trouble finding the right guy to play Patrick Verona, a rebellious high school outcast tasked with getting bold teenage feminist Katarina “Kat” Stratford (Julia Stiles) to date him. He had to be grungy yet charismatic. A likable loner.
“I had already looked at probably 250 guys, and I still wasn’t happy. I still hadn’t found that magic that I felt was out there,” Junger told me at a celebration of the 20th anniversary of the movie’s release, on March 31, 1999. “And Heath walks in, and I thought to myself, ‘If this dude can read, I’m going to cast him.’”
“10 Things I Hate About You” is a modern adaptation of William Shakespeare’s “Taming of the Shrew,” centered on a major conflict: Because of their father’s (Larry Miller) strict rules for dating, Kat’s younger sister, Bianca (Larisa Oleynik), can’t go out with anyone unless Kat gets a date too, leading Bianca’s potential suitors ― her timid tutor, Cameron James (Joseph Gordon-Levitt), and popular jock Joey Donner (Andrew Keegan) ― to strike up deals with Patrick, seemingly the only guy in school who would attempt to woo the ill-tempered Kat.
It’s a tale that has entranced moviegoers from 1999 to today, which is why HuffPost gathered Junger, actress Julia Stiles, Ledger’s agent Steve Alexander and others to recall one of the film’s most iconic scenes: Ledger’s romantic song-and-dance routine on the high school bleachers. In order to make up for not kissing her after a drunken night out, Patrick crashes Kat’s soccer practice with a slightly embarrassing performance of “Can’t Take My Eyes Off You,” accompanied by the school marching band. She, of course, is charmed.
A Cast Dreams Are Made Of
After his successful stint as the director of the coming-out episode of “Ellen” in 1997, Junger had a general meeting with Disney. It turns out the studio was looking for someone to helm “10 Things I Hate About You,” and his enthusiasm for the project persuaded producers to give him the gig.
Gil Junger (director): When I got hired to do the movie, which was, of course, thrilling, I said, “I’m not making a high school movie. I look at this as a relationship movie between two people that happen to be in high school, because I want my 40-something friends to come to this movie and dig it.” I refused to make a high school film in a condescending manner of any kind. I just find the genre to be so derivative.
Steve Alexander (Ledger’s agent): I think the movie really holds up. I have kids, and they watch it today if it comes on, or they stream it or something. It still works, and it’s a testament to the material being strong and Gil casting it so well.
Junger: The only thing the studio said regarding casting was, “You should take a look at the kids from ‘Dawson’s Creek’ because they’re really hot right now.” They basically inferred that they would like me to hire Katie Holmes and that cute guy from “Dawson’s Creek.” For some reason, I think his name was Patrick. Whoever was cute or one of the heartthrobs in “Dawson’s Creek.” [Editor’s note: I threw out James Van Der Beek’s and Joshua Jackson’s names, but Junger wasn’t convinced it was either of them.] I really wanted them to trust me to find relatively talented people who nobody knows, because then there wouldn’t be any preconceived notions at all. It’ll just be this new group of kids that America is watching. I said, “Please just give me a chance to cast this myself. I’ll screen-test them and you can either say yes or no.” And they looked at me and said, “OK, you got it,” which was pretty amazing, since this was my first movie.
Alexander: It was a screen test that came first. We made a test deal for him, and if I remember it correctly, Heath read it, liked it, thought he could play the role well.
Junger: Marcia Ross was the head of casting for Disney at the time, and she was just phenomenal. She brought in the next guy, said he was from Australia and that she didn’t know much about him, but his agent said we should take a look. And as soon as Heath walked in, I just felt, “That is a fucking movie star.” And it wasn’t because of the way he looked. It was just the vibe. There was just an ease of confidence and sexuality that was like, “Whoa, who is this guy?” So, he sits down, and I had about eight pages of sides for the character to read. We’re not even done with the first page, and I said, “Heath, let’s put the sides down.” And he looked at me so scared. I said, “No, no, no. This is a very good thing. I think you’re a very talented guy, and I just want to improv with you for a little.” I wanted to see how facile his ability was to shift attitudes and maybe play off some humor. And we did that for about 45 seconds, and I said, “OK, thank you so much for coming in.” And again he looked at me like, “Dude, I just flew here from Australia. You’re spending two minutes with me for a 16-hour flight?”
Alexander: I don’t even think they looked at the film [from the screen test]. Normally they’ll watch the film and then decide together and do this whole thing. I think they literally called as soon as he walked out of the room.
Junger: Literally the instant the door closed behind him, I said, “I have never wanted to have sex with a man, but if I had to have sex with a man, that would be him. Hire him right now.” And he was hired within an hour.
Alexander: That was the first American film that I put him into. It was a studio movie with him playing the lead guy, so it was kind of just what you want.
Junger: I cast Heath, then I cast Julia.
Julia Stiles (Kat Stratford): I was flown to LA and had a screen test with Heath after the initial auditions. I just remember being happy to have gotten that far.
Junger: The character of Kat, I just wanted to say to kids, “It’s OK to not change or adjust who you are to feel connected to everyone else. Basically, don’t behave in a way to make other people like you; behave in a way that’s true to who you are.” To be honest, I always thought of it as a female empowerment film, so when I met Julia, forget it. She was exactly who Kat was. Just the way she shook my hand, I was like, “This isn’t a girl. This is a young woman to take seriously.”
Stiles: I had never seen a character like that in teen comedies. Maybe there were precursors like Ally Sheedy in “Breakfast Club” and Molly Ringwald in “Sixteen Candles.” Winona Ryder in a handful of ’80s movies. But I was excited by Kat’s outspoken angst.
Junger: I was, like, out-of-my-mind excited. This was the first movie for Heath. The first movie for Joseph Gordon-Levitt. The first studio movie for Julia. So yeah, we cast the shit out of it. We even had Allison Janney before Allison Janney was cool. How do you like that?
An Unforgettable Summer Shoot
The cast and crew descended on Tacoma, Washington, in May 1998, where they filmed at Stadium High School and in and around Seattle through August. The group quickly became a family.
Junger: Directing the cast, I never thought, “I’m hanging out with kids.” We were a team, and we were making a movie.
Stiles: We were all so open-hearted and there for each other.
Alexander: When I went and visited, all the kids — quote, unquote — were, I think, staying in dorms, and they became this little tribe.
Stiles (from a previous interview with HuffPost): We were all staying at the Sheraton in Tacoma, Washington. That was such an amazing time for all of us, and we were all so innocent.
Alexander: Heath had a blast making that movie. He loved it. It was a very close-knit group of people with the producer, director, the cast.
Junger: Working with Heath was so special, and I’m not saying this because he’s dead. I just liked being around him. Most of the days I would have my driver pick me up a little early, and then I’d go pick up Heath so I could take the extra half-hour ride in with him because I just found him to be so freaking interesting. He was amazing.
Alexander: There were so many great people in the movie, and Heath really enjoyed the camaraderie of working with them. He got close with David Krumholtz and Joseph Gordon-Levitt. Also, Andrew Keegan! That pack of guys got close. And he and Julia got along really well.
Junger: The funny thing is Julia Stiles and Joseph Gordon-Levitt were the hot item. I thought every girl on that set was going to be nuts for Heath, and true to form, Julia had her own drummer ― just totally went for the little, supersmart Joseph Gordon-Levitt.
The Scene That Charmed Audiences
Halfway through the movie, Patrick performs a memorable song-and-dance number on the bleachers during Kat’s soccer practice. Originally, Ledger was going to sing “I Think I Love You” or “I Touch Myself,” but he decided Frankie Valli’s “Can’t Take My Eyes Off You” was the right choice. Producers cast a local high school marching band to perform alongside him, which no doubt helped him score a nomination for Best Musical Sequence at the then-prestigious MTV Movie Awards.
Junger: Rather than cast actors who couldn’t play an instrument, I thought, there’s a rhythm to a band. You play with a band and you’re all in sync. And so, if my recollection is correct, I sent casting to a couple high schools to see if they had marching bands. We wanted a whole band.
Frank Caraan (bandleader): The marching band was a mix of actors and actual band members, myself included. The school that the movie was filmed at did not have a marching band, so they had reached out to my school, Lincoln High School, and asked if we could be in the movie. My band teacher was hesitant. I remember saying, “Are you nuts? We have to do this movie!” I was already accepted as an extra in the movie, but I wasn’t about to miss this opportunity to have an actual role.
Junger: The lead guy was some bumped-up extra. For all I know, maybe that bandleader was a real bandleader. I remember he blew the whistle and had one tiny scene in the hallway where Heath handed him $300 bucks. I added that scene in because I needed that connective tissue. Patrick was such an outcast, why would the marching band perform for him?
Caraan: During filming of the bleacher scene, my friends were talking, and we wondered how the audience would know that Heath got the band to play the song for him. A few days after finishing the bleacher scene, I received a call from the production company asking me to come in for an emergency shoot. I wasn’t sure what scene I was going to do, but in the back of my mind, I was hoping for that locker scene. Thankfully the production crew was two steps ahead. When I got on set, the assistant director approached me and gave me a quick rundown. He explained that the bandleader was this guy at school that could get any- and everything done for students, for a price. You needed answers for a test? Ran out of pencils? Need a full-on musical production to impress the likes of Kat Stratford? Go see the bandleader.
Junger: If you remember the way the scene was shot, it opens with the fingers pushing the volume up on the speakers in the control room, and then you see Heath come out of a room and slide down a pole. Well, there was originally no pole there, but I wanted it to set the tone — effortlessly charismatic.
Marguerite Pomerhn Derricks (choreographer): The pole! I think I got that from “Showgirls.”
Junger: I blocked on the fly, but the choreographer created a beautiful sense of movement.
Pomerhn Derricks: At that time, just because of “Austin Powers,” all of a sudden, I became the go-to girl for movies. I had a meeting with Gil Junger, and then we decided to do the movie together. I was sent pictures of the location, and through those, I came up with the idea of how Heath would move. He was my Fred Astaire!
Junger: Not that I’m an aficionado when it comes to old black-and-white films, but I wanted Heath to have that ease and charm of Fred Astaire.
Pomerhn Derricks: I talked to Heath about Fred Astaire and just the couple of little moves that he does — the slides to the side and that long-pass grapevine. It would take an actor like Heath, who was fearless, to not be worried about how he was going to come off, not to worry that it was old-school.
Years later, when I got “Spider-Man 3” with Tobey Maguire, I remember meeting with him and Sam Raimi, and Tobey did not want to dance. There was this whole breakdancing scene that turned him off. I was developing this number and bringing in all these head-spinners to be his body doubles, and Tobey was negative, negative, negative. So one day I went to his house, and I started showing him Fred Astaire stuff, and that’s what we ended up doing for “Spider-Man 3.” But it was because of Heath. I told Tobey, “You doing it is not going to age you. You’re just going to make these classic moves fresh and hip and new.” Watching Heath do that in the stands, that’s exactly what he did. In his youth and his fearlessness, he made them look so cool.
Stiles: Heath just surprised everyone with his commitment to that performance.
Alexander: He knew he wasn’t great, and I think that’s the charm of that scene, of course, that it’s bad. I think he probably went for it in that way, really not being prepared but being as goofy as he could be, running around in the bleachers doing his thing.
Junger: He was running take after take, up and down those steps. I was actually very surprised at Heath’s athleticism while singing because, yes, that was him singing. Like, of course he could fucking sing too, right? He could wear green leather pants and sing! Fucker. I still resent him. Is that foolish?
Caraan: In addition to having my high school’s band march in the movie, it’s our band that recorded the music, and we were able to watch Heath Ledger record his vocals for the scene. He was very nervous, stating that he never sang in front of anyone before. But he nailed it.
Pomerhn Derricks: The singing impressed me more than anything because, as a choreographer, I can always find a way to make actors look amazing. But singing? That’s something you can’t fake.
Alexander: He sounds terrible, yet he’s super-charming and has a great smile ― that’s what makes that scene work.
Junger: At one point I was getting ready to do a camera take, and I see someone lying down in the bleachers. One of the two cops who were supposedly chasing him in the bleachers thought he had a heart attack. He was like 50 and overweight and had such shortness of breath, so they called the paramedics. It was the perfect irony or juxtaposition to the youthful exuberance and power of Heath. It was actually the guy that Heath spanked on the butt when he ran past him.
Alexander: He was always silly and fun, and there’s a lot of his personality in that scene that shines through. Later on in his career, he spent most of his time figuring out ways of disappearing and not sharing as much of himself in his roles while trying to create characters. But I think there’s a lot of Heath in Patrick Verona, at least in certain moments.
Junger: Heath was wildly magnetic, but I got to say, just those looks that Julia Stiles gave, from “Ugh, it’s that asshole” to “What’s he doing?” to “Who’s he singing to? Me?” to “Oh, my God, I love that man.” I mean, she did it all.
Stiles: That’s so nice of him to say. It wasn’t hard to just react to what Heath was actually doing.
Junger: I just couldn’t believe it when she read for me, because I just knew, holy shit, is this girl deep. And she was! She’s crazy smart. I think one of the reasons the scene worked so well was, of course, the gymnastics of Heath and his charm, but it was also her reaction and how moved she was by his efforts. It was a beautiful two-hander, let’s say.
The Making Of Stars
Ledger’s and Stiles’ performances in “10 Things” put them on the Hollywood map, to everyone’s delight. He went on to appear in “The Patriot” and “A Knight’s Tale,” and she booked lead roles in “Down to You” and “Save the Last Dance.”
Stiles: I had done a few bit parts and an indie [“Wicked”], but “10 Things” was my first lead in a studio movie and the first thing people really saw of me. And it’s a rare privilege to make a movie that people remember 20 years later.
Junger: I told Heath, “Look, I just want you to know that when this movie comes out, you’re not going to know what the fuck hit you. People are going to be clamoring to work with you, and I bet your next offer is going to be a million dollars.” And as a new friend, I was just telling him to do his best, to remain who he was: an old soul, mature, not distracted by drugs. Then he said to me, “I really appreciate the advice, but rather than worry about what’s going to happen, help me be the best I can today.” For an 18-year-old who’s getting his first movie ― and that first movie is with a Disney studio ― and that director of your first real movie is telling you you’re going to be a huge star, any kid I know would’ve been like, “Oh, man, that’s so fucking cool! I hope so!” Not Heath. He just wanted to be the best he could in that moment. That’s so telling of who he was.
Alexander: So much has been written about Heath being that old-soul guy. He did have a maturity about him. He left home at a young age and kind of got a lot of life in quickly. So for a young guy in his early 20s, he felt older than that in the way he carried himself and the way he thought about things. I think that’s what made him special, even in the early days. He would say he wasn’t as capable as an actor until later, but he did a pretty good job in “10 Things I Hate About You,” pulling us all in. And he had a lot of fun.
Pomerhn Derricks: The thing I remember most about working with Heath was he and I just sitting on the bleachers. It was beautiful outside. I remember sitting with him for hours and talking to him about Australia and him coming here and his desires and dreams. I’m crying right now remembering this shoot.
Alexander: It’s funny, coming off of that film, he was offered so many more teen comedies, dramas, those kinds of stories. But he did that one, and that one was it for him. When he pivoted and wanted to look for other challenges, it was amazing how many he passed on after that film. I remember the year that we went to the Venice Film Festival, and we were there for a week, and every day he was talking about a different film. It was “Brokeback Mountain,” “Casanova” and “The Brothers Grimm.” And he had “Lords of Dogtown” in the can, as well. It was this incredible, very, very different group of films and characters.
Caraan: Prior to his passing, I was very excited when I heard he had gotten the role of the Joker in “The Dark Knight.” There were so many people that were apprehensive with that decision and if Heath could step up to fill such an iconic role. I remember watching it in theaters, and all of his scenes were so intense, I felt I was actually in those scenes. When he won the Academy Award for his performance as the Joker, I teared up a little bit. It was humbling for myself, as I was a small piece to his entire legacy. But it was bittersweet.
A Short Life Well Lived
Ledger died of an accidental drug intoxication on Jan. 22, 2008. He was 28 and the father of then-2-year-old Matilda, his daughter with actress Michelle Williams. In the years he spent in the industry, he starred in 16 films and earned two Oscar nominations, posthumously winning Best Supporting Actor in 2009 for “The Dark Knight.”
Junger: Two weeks before Heath died, I was just finishing a script for a film that I wanted him to star in [“10 Things I Hate About Life”]. I called Steve Alexander and asked if Heath could give me a call so I could share this exciting project with him. He said Heath would be taking no work calls at all while he’s filming “Dark Knight” because he’s so far into the character that he can’t get out of it and he’s having incredible trouble sleeping. That role shook him, and he took it so seriously and so professionally and profoundly that he couldn’t escape it. God, it gutted me because I knew it was a wasted life. I knew he wasn’t playing with fire. I knew he wasn’t that guy.
Pomerhn Derricks: I’ve worked with so many amazing actors, but he was somebody I wish I would’ve worked with again. I was a big fan of his and watched him develop into this amazing actor. I would’ve loved to have done something a little deeper with him. Not only did we all love him for his work; he was such a sweet soul. As a fan, I feel we missed out on so much more, like, what else was he going to give us as an actor? He had so much.
Alexander: I’m incredibly proud of the career that we built together. Obviously, it was his incredible work on screen, but there’s a lot of thought that goes into the choices these artists make, and I feel honored to have worked on that career. When you look at it now, it’s just … it’s great work. All of it. It’s not an overly long resume because he only had a short period of time, but the work is so strong.
Stiles (from previous HuffPost interview): I dug up this old note that he had written on this hotel stationery. … I forget the beginning of the quote, but it’s like, ‘Dance like you’ve never heard the music and love like you’ve never been hurt.’ It was so sweet. I almost cried. That was his goodbye note to me.
Alexander: I have so many memories and things to remember him by, but I have one tattoo on my arm that says, “Wish you were here,” which is something he had on his body. It’s just a constant reminder. He’s a part of my life in lots of different ways, still.
The above interviews have been edited and condensed for clarity.