WHAT WENT WRONG - Featurette: 10 Things I Hate About You (with Two Judgey Girls)

Episode Date: July 17, 2026

How did Shakespeare’s ‘The Taming of the Shrew’ become one of the greatest teen comedies of all time? In this Featurette bonus episode, Chris, Lizzie, and special guest Mary from Two Judgey Girls explore the movie that introduced Heath Ledger and Julia Stiles to the world. Find out why the screenwriters clashed with the director, which role Joseph Gordon Levitt really wanted to play, and how that bonkers helicopter shot came to be! Plus discover why this Seattle-based shoot was magical for the cast. Our Featurette episodes are shorter, more relaxed explorations of films we love that don't have quite as much behind-the-scenes drama as a regular What Went Wrong episode... but they’re too fun to skip! Hosted on Acast. See acast.com/privacy for more information.

Hello, dear listeners, and welcome back to a special episode of your favorite podcast, Full Stop, that just so happens to be about movies and how it's nearly impossible to make them, let alone a good one, let alone a movie that takes place in Seattle and was mostly shot in Seattle and a little bit in Tacoma, but that's fine, it's close enough. It's what went wrong, and we're doing things a little different today. And to explain that, I'm going to send it over to the person who came up with the brilliant idea for today's format at all, Lizzie Bassett. So celebrate her, blame her, I leave it to you.

Great. Love that responsibility. Yes, so this is a featurette, folks. This is not a full-length feature episode. This is just a featurette because initially we did a poll around, I believe, rom-coms that people wanted covered, and the one that won was 10 Things I Hate About You, and I didn't think you all were going to pick that.

So I hadn't done enough research into it. And then when you did pick it, that. I started looking into it and I thought, well, there's not actually enough here for a full episode. So we kind of put it on the shelf and forgot about it. But then I thought, you know what, it doesn't matter. It still deserves its place in the sun. So we thought, why not do slightly shorter episodes, call them featureettes and still, you know, give these movies their time to shine. So it's a different kind of bonus episode. Let us know if you like this. As I said, today, we were discussing 10 Things I Hate About You. And we have a special guest joining us to help us revisit

this William Shakespeare classic. We have Mary from Two Judgy Girls. Hi. Hi. Thank you so much for having me. I'm so excited. Of course, absolutely. And can you tell us a little bit about your show before we dive in? Yes. So Two Judgy Girls is a daily podcast and we talk pop culture, but really are focused on Bravo TV. It's the 20th season of Real Housewives of Orange County. We will be deep diving every single episode. Lizzie was on recently and we talked the Valley. We'll be doing NextGen NYC. Anything that has to do with Bravo, we are covering. So if you want to head over to two

judgy girls and give us a listen and follow us on Instagram, please do. You definitely should. And I want everyone to know that Mary is so committed that she sings the theme song to the Valley every time they cover it, which is, there it is. Givers are here. It's so funny. All right. Well, thank you so much for being here. We're thrilled to have you to talk about this movie. So let's start with you, Mary. What was your relationship to 10 Things I Hate About You before now? And what did you feel rewatching it for the podcast? Rewatching it gave me so much nostalgia. I actually owned the soundtrack. I had it on a CD. And so every single song I was singing to my husband as I was rewatching it. And I haven't seen this movie since I've. was in middle school. So I think this came out when I was in seventh or eighth grade. But, you know, when you had the CDs in your car, you listen to an entire CD the entire way through. And so like, that was giving me life, all the music. And I also feel like the fashion is really in right now, all the clothes. It also just this movie like held up. I feel like a middle schooler now would

enjoy it just as much as I did 20 years ago. Nice. I agree. I had a similar experience with the soundtrack, which we can get into. But, Chris, what was your experience watching this? Watched it with Carmela, who's a huge fan of this movie. On the spectrum of American Pie, ones that don't hold up to clueless, sterling, like a diamond, will never dull. This is much closer to clueless. It's not quite clueless for me, although I do think it gets better and better as the movie goes on. And so, especially I think as you focus more and more on Heath Ledger's relationship with Julia Stiles, the movie improves. And he is so unbelievably charming. And she's great. I really love her speech at the end. I forgot how good she was. Her dad, whose actor is escaping me is

one of my favorite, like dry comedy, delivery, you know, parent performances until, I mean, I was trying to like, Stanley Tucci and EZA or something like that would be like the next one that comes long. The wildly inappropriate Alice and Janney is just weird, like erotic literature subplot, flashing the t-shirt. There are a few things. Do they hold up entirely? I don't know. There can be one or two scenes where, you know, they kind of default to a cheap homophobic or sexist joke because it was the time. That's what we did in 1999. But overall, I agree. I think this movie holds up really well. It's so fun. I do think it has a really great heart to it, ultimately. And that really comes down to the performers.

This movie has a great cast. Obviously, Julia Stiles, Heath Ledger, but the only one who looks like he's actually in high school, Joseph Gordon-Levin. By the way, aided by the fact that he's next to David Krumholtz, who looks like a 45-year-old man, even though he's not. After they cut on every take, he is getting a hot lather shave

trying to get rid of the 5 o'clock shadow after every single take. But also, Andrew Keegan makes a great heel in this movie, He's very funny. Obviously, Gabrielle Union, I forgot. Like, we're seeing her just... You know, she's the oldest. Is she? She looks young. She's 10 years older than everybody. Oh, wow. Because Heath Ledger's 19 when he films this. He's 19, and he looks older, to me. I agree with that. But Julia Stiles is 17 when she films. She's very young. Yeah. And I feel like most movies, when you watch a high school movie, like the Breakfast Club or something like that, they're like...

Yeah, they're all 45. Exactly. So to me, I was like, okay, I was like, okay, I was. I am watching someone playing a high schooler that could actually be in high school. Yeah. That was kind of shocking. Yeah. I was surprised that Heath Ledger was 19 because he does look older. Me too.

I thought he was older. And Larissa, is it Olenik? Olenik, I think. Olenic, the secret world of Alex Mack I had totally forgotten about. She's really fun in this as well, the show where I believe her secret power, she becomes a puddle. Yes, I watched Alex Mac. And she goes underdores. I loved Alex Mac.

A Nickelodeon. Yeah. Really enjoyed it. Also loved the soundtrack. Just opening with one week, I was like, oh, we are back in it. Yes. Right now, this movie, I think, definitely one of the top five 90s teen movies that you would put in a time capsule and keep. Like with She's All That.

She's All That would maybe be number five. Hey, She's All That is good. It's good, but it's not quite on this level for me. That's fair. I love it. That's fair. I, like you, Mary, I had the CD. to this. And so I had the same experience. Every single time a needle drop started, I was like,

I have a lover who loves me. Every song. I knew every lyric to every song, like all the way through. I was singing along. I just had the best time. I have to give a shout out to the music supervisor on this movie, whose name is Ralph Sal. This soundtrack is incredible. And just FYI, this guy also did The Craft. He did Dick and Three Kings the same year as this. Mean Girls, Harold and Kumar go to White Castle, so many more. We don't talk about music supervisors that much, but like, this soundtrack is an absolute banger. Do you listen to Girl Talk? Or did you in high school? So Greg Gillis samples almost every song on this album, I feel like, especially in his first couple of albums in particular. There's it's so, you're right. Yeah, there's a lot that's used in this. It's so nostalgic. The songs in

particular, but I'm totally with you. The outfits, I forgot how much I wanted to look like Julia Stiles and Ten Things I Hate About You. And you know what? I still do. I think her outfits are amazing. Her hair, come on. The perfect curl. It looks absolutely incredible. It's the perfect curl and the little braids. Yes. If only. I can't. My daughter would rip them out of my head. But back in the day, I would have loved it. I'm with both of you. I think this holds up incredibly well. I was a little nervous rewatching it because there were a couple moments where I was like, oh, no, is this going to not quite stand the test of time? And then it really, really does. I'm with you that there are a few moments. And actually, I think we're going to learn over the course of today that some of the moments that maybe don't work as well were not in the original script. So we will get into that. But yeah, I just was so pleasantly surprised by this. Heath Ledger is so unbelievably attractive and charming and just so clearly a movie star from the second you see him on screen. And it was fun to go back and see his, this is his big break. This is his first big movie.

same for Julia Stiles. Yeah, actually the biggest star in this movie was probably Joseph Gordon Levitt, which is like, funny to remember, but he's coming off of Third Rock from the Sun. So, all right, let's get into it. Here's the details, as always. Ten Things I Hate About You was released March 31st, 1999. It was directed by Gill. I believe it is younger. That's how I'm going to pronounce it. It's J-U-N-G-E-R. Written by Karen McCullough and Kirsten Smith, of course, based on the Taming of the Shrew, favorite Shakespeare plays. It stars Heath Ledger, Julia Stiles, Joseph Gordon Levick, Gabrielle Union, Andrew Keegan, David Krumholtz, and a hundred million more people. The cast of this is, and the IMDB logline is, a high school boy, Cameron, cannot date Bianca until her

antisocial older sister Kat has a boyfriend. So Cameron pays a mysterious boy, Patrick, to charm Cat. Patrick Verona. Every teen 90s movie was based around a bet of some kind. Like, it's always a bet. She's all that. Cruel Intentions. This. To be fair, those are also all remakes. She's all that as Pygmalion and Cruel Intentions as Dangerous Liaisons. Yeah, they're all pulling from far more salacious material. I feel like only Cruel Intentions really leans into it in a really gross, but kind of awesome way. I love Cruel Intentions. I do, too. That is a weird movie. Ryan Philippi's never been better. It's true. All right, so in 1996, a young woman named Kirsten Smith was living in L.A. and working for an indie production company as a script reader, which means reading scripts, querying letters, probably writing coverage. I did this early on. Chris, you've probably done this at some point. She had one screenplay of her own under her belt and wrote poetry in her spare time. But one fateful day, she got a query letter from another young woman, Karen McCullough, and this one caught her eye. Because McCullough had bounced around, Mark.

marketing and PR jobs in D.C., she moved to New Mexico. She was like, there's jack shit to do here, and then settled in Denver where she started cranking out screenplays, like nine or ten screenplays. So in this query letter, she included log lines for each of these scripts. And Smith really liked them. So she wrote McCullough back and asked to read a screenplay. She really liked that. So she asked to read another. And finally, she called up McCullough and said, hey, maybe we should meet for drinks if you're ever in L.A. And McCullough was like, I'm on an airplane now. So they met up. They got drinks, and they started writing their script together on a cocktail napkin that night. And that script was not 10 Things I Hate About You.

According to The New York Times, it was a, quote, Female Action Thriller about girls who kill members of the Navy Seals. Oh, wow. That's fun. Sure. Instead of clubbing baby seals, it's clubbing Navy Seals. That's right. Very good.

So Smith said they wrote it, quote, because we were like, long kiss good night is going to be a huge hit. Everyone's going to want more female action. It wasn't, and no one wanted our script. Blan Kiss Good Night. Pretty good. Well, not according to everyone in the 90s, apparently. But that didn't stop these two.

They looked around. They saw that teen comedies were selling like hotcakes, because they were like, fine, we'll write one of those. And they went a little slower this time. There was no feverish writing on cocktail napkins, but there was some source material. McCullough had always been an avid writer, and she had a collection of high school diaries.

Do either of you ever keep a diary? I don't. I did. You did? Have you read it? I'm too embarrassed to reread it. And even in college, when I would go on trips, I would write a diary entry the next day of what happened the night before. Oh, my God. You have to read it.

I'm genuinely scared to read them because I feel like... You should get drunk with your husband and you should read it. We did that with... I did that with Carmelas. We did that together with her middle school diary from when she was in sixth grade. And it was the most amazing. I can't. I will.

I definitely have it. I can't reveal anything because it's too personal. It's just incredible. Alternating between some of the most insightful, intelligent things you would never expect an 11-year-old to say, followed by hands-down the dumbest take in the history of the world. And so it was just amazing. It was so charming. Okay.

Mine's probably from 17 to like 22. So I'm sure those are good years. There are some interesting stories in there. I feel like I would rewrite a story from the night before of what happened. You got to go back and look. Okay, I will. That's exactly what McCullough did. So she pulled out her high school diaries and she's reading them.

And that's when she found a list called 10 Things I Hate About Anthony, written about a boyfriend she didn't particularly care for. So she brought it to Smith, who immediately was like, that's our title. But they still don't have a story. And then they saw Amy Heckerling's clueless. And they thought, that's it. If she can pull from Jane Austen, because obviously clueless is Emma, then why can't we do that? So they go looking for anything, fairy tale, story, play, novel, something they could use as a jumping off point.

They searched high and low for two months, and they kept coming back empty-handed until a friend suggested the taming of the shrew. Smith said the more we read the play, it just felt like a perfect adaptation and something that had all of the great Shakespearean turns and twists, but also could be modernized in a really cool feminist way. I really don't like this play, but I like what they did with it a lot. So Smith and McCullough set out to write their outline the same way any aspiring screenwriters would. They hold up for a week in McCullough's timeshare in Mexico that she bought when she was really, really drunk. She'll never get out of that. She's still paying for it now. My grandparents had a timeshare, and I think my parents were forced to inherit it, and they were trying to get rid of it.

It's a curse. It is close to a curse. as exists in this world. Well, she got hammered and bought one. So then they wrote the whole thing by sending pages back and forth via actual mail and facts. Now, they acknowledge that the internet probably did exist

but that Kirsten just didn't have email. So this is how they did it. And it's fun because Smith said, we had a lot of debates, but I think what comes through the movie is so personal. Karen has a great sense of humor. She loves a dick joke.

I love bikini kill and indie rock music. I was a poet before. We both love a really strong-willed feminist leading character. We just really want her to be very defiant and didn't care what people thought about her. We wanted for her to be punk rock. Now, Smith is originally from Seattle, but they set the script in Portland, Oregon, the Pacific Northwest location, partly Smith's origins, but also they really wanted to differentiate this from Clueless, which is obviously very clearly set in L.A. So they finished writing in January of 1997 and immediately started shopping it around everywhere. Like everywhere.

They took the script to Sundance. They took it out to different producers who tried shopping. it around. And finally, they got a manager who, through a daisy chain of events, manages to get the scripts into the hands of Touchstone, which is, of course, owned by Disney. Now, Smith described this year for Disney as the, quote, teen movie lottery of 1997. Basically, Disney was looking around seeing that teen movies were making money, and so they were just putting the word out trying to buy a bunch of teen movie scripts. And he had things like, you know, Scream had redefined like Slashor movies, 96, I want to say, and had done huge bits. And it had done huge bits. And

So everything, you know, rated R all the way down to PG, these movies are minting money. I remember every Friday night in seventh and eighth grade, I went to the movie theater. It didn't even matter what movie was on. That was just something to do to occupy your time. And I went every single weekend to the movies. Yeah, me too. You could even argue that, I mean, this wouldn't be until the same year as 10 things, but even something like Blair Witch has a teen feel to it. They all did at this point in time.

There was such personality, I feel like, to, not that there isn't now, but there was such outward personality to teen culture where I think what's hard about trying to capture teen culture now is that it's so integrated into the internet and it's really hard to make that visual in a lot of ways. But when it works, like obsession, right, they came up with a metaphor that works, people really show up for it. And that's how people were showing up for these movies in the 90s. And like a Titanic where you saw it seven times.

Oh, Titanic, a great example. I always forget that they're so young. when we were younger than them, so they seemed grown, and now I watch it, and I think, your children! They're like 19. Yeah. Women and children first, that's you.

I think she is 19 in that. And he's, I think, 17. But I mean, that was a movie that you saw in the movie theater. I saw it seven times in the movie theater. And it was amazing. There was such a long period of time between seeing it in the movies when it was actually then released to DVD or VHS, the waiting period. It's like, because six months when you're there,

that old is, you know, five to 10% of your life. Completely. You think, oh, my God, I've missed it. I'm never going to see it again. This was also the time where you would go into Blockbuster and hope to get it on the Friday night. And if you weren't there on time, you'd have to go to a different movie that they had in stock. It's so crazy that now everything is so on demand and you can get it immediately.

Yeah. So Disney put Smith and McCullough through some rewrites. but the thing is they were up against another script going through the same process. Ultimately, when the time came, Disney had to decide between 10 things I hate about you and something that might really have been called school slut. No. That's really? Yeah, I think so.

Doesn't feel very Disney. No, it doesn't. I think they might have changed the title. They chose 10 things I need about you. Working title school slut. But they did want to know why was Kat so dang angry? That was their big thing. She's so angry.

Why she has everything she could possibly want. Why is she angry? And they're like, she just is. It's okay. Like, it's okay for a girl to be angry. And they said, hold that thought because no. In six months from start to finish, Smith and McCullough had sold the second script they'd ever written.

Now they had to find a director, and Disney sent the script around to every agent looking for the right person for the job. And they ended up hiring a TV director who'd never helmed a feature before. That's not really giving Gil Younger enough credit, though, because he had directed a ton of TV and actually had just directed the coming out episode of Ellen. Do you remember that? I don't. I mean, well, I remember discussions of it.

I don't remember the episode. Got it. I mean, it was a big deal. Mary, did you ever watch that? Yes, yes. And then because she did that, she got canceled. Yes, yeah. It was, I mean, it was a huge deal. Say what you will about Ellen, that episode was pretty groundbreaking. And it was this episode that pushed Gil into wanting to direct a feature because he had such a good time doing that and the emotional weight of it and everything. He thought if one hour's good, two hours must be better. As a TV director, had he directed, I'm assuming he probably directed a lot of young actors. Yes, he as well. And so that gives him an advantage also. He knows how to work with young people. He probably can work on a budget and work really well in a tightest.

schedule. Yeah, this budget is not huge. New York Times reported it at about 11.5 million. I've seen up to 13 million, but I mean, pretty small. Good scope for that. It ends with a helicopter shot over Stadium High School. Well, we'll get to that. All right. So he got a meeting with Disney and told them, it's perfect. No notes. Just kidding. He actually had two very specific problems with the script. The male and female leads. He really, really didn't like them. He said, Julia Stiles' character was just cold and arrogant. What I needed to know is why? Why is she that way? There's some type of emotional pain, so she's very guarded. Heath Ledger's character felt like he was just weird for weird's sake. Again, what are his emotional underpinnings? Why is he a bit of an outcast? What is it about him that

caused him to behave this way? I think those are good notes. I think audiences always wonder those things. I agree. They at least need a hint. Yes. And you get an explanation with her and a hint with him, I would argue, and I think that's enough. I'm with you. I think these are good notes. I'm not sure I love the other elements that he added to this movie, which we will get into. But I think he's spot on with this. So I guess Disney enjoyed being nagged because they hired him. And as soon as he'd gotten the job, he realized, oh my God, I don't know what I'm doing. So he went to Borders Books and Music, RIP, and bought six books. Yep, bought six books on how to direct a movie. Only I started reading all of them. Ben there.

How did you direct a movie for dummies? Yes, literally. Just give me the dumbest. version. That's probably what he bought. He was like freaking out having a panic attack, flipping through the idiot's guide to making a feature film. But there's one thing younger new from the start. He did not want to direct a typical high school rom-com. He said, I want to direct a movie that my friends will also love. So a movie about truth, a movie about relationships, a movie about love, as opposed to being the central focus, high school kids, and the typical condescending high school movies that are made all the time. I think he achieves that goal. Almost a little like Dawson,

Creek-esque. The vocabulary is intelligent. Dawson's River, as it's called. Yes. Those Dawson's River kids climbing into each other's bed, which is like a direct quote from my mom talking about Dawson's Creek. I wasn't allowed to watch it either. I was allowed to watch rated our movies in third grade. Me too, but not Dawson's Creek. Oh, exact same. I watched Dawson's Creek with my mom. And I think I would ask her, what does that word mean? Yeah. And she'd be like, nothing. Yeah. It's Spanish. Don't worry about.

Now, according to Younger, he made some pretty big changes to the script pretty quickly. He says he asked four of his best friends who happened to be major showrunners at the time, which does make sense. He was a sitcom director to get together and help rewrite the script over the course of four days. He also said they removed about 28 pages from it. Now, he acknowledges they made pretty big changes to the script, but that according to him, the core of the film was on the page. I

We're going to talk about the screenwriters a little more and what they went on to do I'm inclined to believe they added a little less to the script than he is hinting here but who knows can I point out an example of what feels like a showrunner added joke?

Sure, I wonder if you're right. When Joseph Gordon Levitt says not in a prison film sort of way right? When they're they're, he's like we're going to be your boys. No, that might be the screenwriters. Okay, because that just to me felt like

the scene had already moved on. Why are we dropping this joke that's in Congress, honestly, with his character as well. So anyway, that was just an example of one that stood out to me that I felt. That's interesting. I feel like that one. I don't know about some of those sort of quips, but we will... Lizzie. What?

Loves a good prison, don't you? Listen. He delivered it well. You're Michael Scott in the out. Don't drop the soap. Don't drop the soap. All right. As you might imagine, our two screenwriters did not love this approach.

In fact, they didn't get along with younger, particularly well at all over the course of this. He came from the sitcom world. He really wanted to add a lot more physical comedy gags. So those are the big things that they added. Crumholtz shooting off. Yes. The party when the window shatters.

That one I didn't care about. The motorcycle, I actually think, is funny. It's one of the few that I think works. I like the motorcycle. I think it's a funny prefall. But that is the one thing upon watching this back, and maybe it was colored by the fact that I had done this research, but there's too many. Like, at a certain point, there's too many arrows in the

butt, you know, like... I agree. Yeah, the golf ball, the arrow. It starts getting a little... And I think it actually starts to take away from the great physical moments of her dancing on the table and him dancing down the bleachers. And, like, because him going down the bleachers is one of the most iconic moments in 90s teen film history. Which that's for sure in the script, by the way. Yeah, and her on the table, she's great. I mean, that's... I know we all talk about the say the last dance audition, we should be talking about Julia Stiles on the table and 10 things I hate about you because it's so fun. They're connected, Chris.

All right, so they really hated these physical comedy moments. They have since acknowledged that most of the moments work. However, they actually really don't love the motorcycle sequence. I think that's the best one. It's so funny. I need to. To me, it also gives scope to the set and the set. And the setting. So I believe that you're looking at commencement bay that's in Tacoma. It's a really

beautiful football field. It's a cool shot. It helps establish the geography, which will later come to play. But they're at an actual school. Yeah. When he goes down the bleachers, which are on camera right as you do the shot. To me, that one feels justified and like it serves a story purpose. I agree. But from there on out, they start to get a little tiresome. Well, the arrow, once you hit the arrow on the butt, you start to think, What movie am I in? Yes. It's just a little weird. But so the big. changes made to the script seemed to be around Kat. Now, originally, Kat's mom was very much present in the screenplay. But according to McCullough, everybody was like, why is Kat such a bitch?

What if her mom left? And that's why she's such a bitch. She said they're like, okay. Which is so funny. Smith said, I mean, with the female characters, it's like she's got to have a reason to have an attitude problem, because if you have a vagina and an attitude problem, there needs to be an explanation. I understand both sides of this. I understand. And what they're saying, I personally don't mind adding in the stuff with their mom missing. They don't like the scene with the mom's pearls that was added. Maybe there was a less ham-fisted way to do this. It doesn't bother me, I will say.

To me, it emphasizes the importance of her relationship with her sister. And so that's why I like it, is that it and their dad a little bit. To me, then I understand their father's character more. So, again, I don't like the sexist valence of the logic. But if the note had just been, I'm worried that the audience is going to keep wondering why this character is the way they are. We should probably give them a reason. I think that's a valid note, is all I would say. I agree.

And upon watching it this time, you know, I always used to think, like, oh, my God, she's perfect. Like, of course everyone would love her. This is ridiculous. Watching it this time, I was like, no, okay, she is actually an asshole and, like, pretty difficult to get along with, which is why maybe in a weird, twisted way, she kind of needed this set of. up to happen in order to have the connection with someone like Patrick in the scenario of this movie and that he did too, like that they're both sort of unable on their own to kind of bridge that gap. And I liked the way that this set that up. I think it achieved that very well.

I wanted more of both their backstory from the beginning. I definitely felt like I wanted more of him, because I feel like we get even less at him. They just threw it in at the end and was like, I lived with my grandfather for a year when you had all these crazy stories. Like, he doesn't even have a liver and whatnot. But also, that's kind of a crazy story. I fed my dying grandpa SpaghettiOs for a year and, like, lived on his couch. And he's just smiling and, like, dipping her in the dance as he does it. And we just move.

She has no follow-ups on that. Well, that's interesting. I would like to know more. Yeah. No. Not allowed. Nothing else. They also really didn't like the moments they found.

incredibly unrealistic, like when Patrick calls in a favor to bring letters to Cleo to prom. Yeah, I don't know what favor that was. Yeah. Both the screenwriters were like, a favor to who? How does this work? Goldamaya. Yeah. Yeah. Okay.

Sure. But when it came time to casting, Disney really wanted big names in the lead roles, and they had two people in mind for Kat and Patrick. And guess what, Mary? They're Dawson's Creek stars Katie Holmes and James Vanderby. Wow. Oh, I did not know this. That's shocking.

It would have been such a different movie had they been the ones. So much lower energy. I love you, baby. For whatever reason, they didn't work out, and those roles remained some of the last to be cast. Now, in the meantime, Joseph Gordon Levitt was one of the first people to join the project. And again, he's probably the biggest name coming off a third rock. from the sun. But he was a bit of a tough sell. He really did not want to do teen comedies. He wanted to do indie films. He wanted to do Sundance. And remember, this is 90s Sundance. So it's like peak

actual independent films. Can you do like, was it mysterious skin that he did? Yes. Shortly after this. Yep. And then of course he goes on to do brick and yeah. So he does do it, but he did this first. He auditioned and he actually wanted a different part. Do you have any guesses what part he wanted to play in this movie. Patrick. It's not Patrick. I mean, then I have no educated guess. A hot model.

What's his name? No. He knew himself better than both of you. Then is it the David Krumholtz character? Yes, he wanted to play Michael, the David Krumholtz's part. He thought it was really funny. That's what he wanted to do. But of course, after reading for both, they came back and they were like, yeah, no, you're

the biggest star joining this. We're offering you Cameron. He still was like, I don't really. really want to do it. And so younger Smith and McCullough met with him and heard him out about all of his concerns. They knew it's important to get him on board. They don't have any names attached yet. And according to McCullough, Smith took a pretty big swing in this meeting. She said, quote, he was trying to get a handle on the character. And Kirsten whips out. He's like Luke Skywalker. And Joe's just sitting there nodding like, all right, all right. And I'm standing there thinking, what?

Go buy yourself a Star War. I love this. I love that the other one's just like, I have No idea what you're talking about, but he bought it. He's like Luke Skywalker, if he tried to trick Princess Leia into dating him. Yes. Exactly. Now, for the role of Cat, they saw tons of young women, including, as we said, Katie Holmes, but also, she's all that, Rachel Lee Cook. What about Kirsten Dunst? Wasn't the virgin suicides around this?

I did not see her name, which I think is interesting. They looked at Summer Phoenix, Melissa Joan Hart, Eli, Eli. Zajsa Dushku, Lauren Ambrose, Gabby Hoffman. Young Gabby Hoffman. Interesting. Very young. Alicia Wick. Carrie Russell. And of course, Larissa Olanick, who would end up being cast as Bianca instead. She actually really wanted to play Cat.

And so when she was auditioning for Bianca, she apparently did it like she didn't really give a shit. And she thinks that's why she got it. That's pretty Bianca. Yeah, exactly. And then Anna Pacquin and Kate Hudson were involved. And they actually offered it to Kate Hudson, who turned it down because Goldie Hawn didn't like the script. Oh, that's so interesting. I know. I wonder what she didn't like about it. Maybe she didn't want her to get like labeled as this alternative person or something. She wanted me more like girl next door. Maybe because almost famous was 2000. When was almost

famous? It was right around this time. It was almost 2000. It was almost exactly this year. Yep. She might have been holding out. I wonder if it was the high school thing where she said, no, you don't, you know, you don't want to get stuck in the high school. role sort of thing and let's try to move you past it. I wonder if she was older too. Yeah. No, she's same age as Heath Ledger. So she was pretty young. Well, only Goldie Hawn knows.

So finally, Younger got a call from the head of casting at Disney and asked if he'd be willing to meet with one more actress. She'd only done one indie film. Her agent's really pushing her for this. And Younger's like, fine. And so he met Julia Stiles that evening. And he said, quote, the first thing that struck me about Julia is that she didn't give a shit about how she was dressed. She was being herself. The second thing was the way she

extended her hand and gave me a firm handshake. There was so much confidence in that. I literally thought, God, I hope she can act, because if she can, this is going to be the girl. And of course, she could. As soon as they left the audition, he called Disney and said, hire her. Now, Stiles was thrilled because she'd been going out for a ton of teen comedies at this point. She was getting nothing. She kept being told, you know, you're not bubbly enough. You need to be more cutesy, smile more, be a little more effervescent, and that's really not her. So when she read the role of Cat, she felt like she could finally breathe, although she does acknowledge that it was more sort of aspirational for her at the time,

because being that assertive even in her own life was something that she still struggled with. And again, she's very young, to your point, she's like 17, 18. Now Younger brought in David Crumholt, so he knew from the sitcom world to play Michael, but plot twist, he wanted to play Cameron. Let him switch. No, you can. I know. No. Sorry, boys.

I know. You can't. No way. Well, as the shoot date approached, they had one role left to fill. Of course, it's Patrick Verona. Now, Younger says he read somewhere around 253 guys for the part, which he points out means that casting had probably read something like 2,500 guys for the part. Wow. No one was right. They were not finding him.

And then casting director, Marcia Ross, asked if he wanted to take a couple of people. a break during one of their marathon casting sessions and Younger said, no, just bring in the next one. And she's like, okay, this next guy, I don't know anything about him. He is here as a favor to his agent. Please don't judge me if he sucks. I really don't know what we're going to get. And of course, in walked Heath Ledger. In a white Saturday night fever suit and black shirt, he was both way too dressed up and extremely rumpled because the suit was not pressed and he looked pretty cool. I mean, 15 years earlier, it would have been Johnny Depp, right? Or 12 years earlier.

And so you were just waiting for, and like, Leo never did this type of movie, you know, but you need that movie star guy here to really elevate it. And Ledger just lands in their lap. It's crazy. Younger said he took four steps into the room. I hadn't said hi yet. He hadn't said hi yet. He's walking towards me.

And I thought to myself, if this fucker can speak English, I'm going to cast him. And then he has an Australian accent. They're going to have to explain in the sense. That's what I was thinking. So he must introduce himself, speak in his accent, and then switch over to sound. I don't know. Yeah, I wonder if he didn't even do an American accent.

I don't think he even did an American accent. I don't even think he tried. Wow. He's like fresh off the boat from Australia. I know in the movie when they're like, I lived in Australia until it was 10. I was like, bitch, you lived in Australia until 10 minutes ago. 10 minutes ago. Yes. Exactly.

Apparently, Mrs. Younger's recounting of it, he turned to the casting directors and said, ladies, I've never wanted to sleep with a man. But if I had to sleep with a man, that would be the man. Cast him immediately. It'd be this 18-year-old boy right here. Good times. Now, of course, it wasn't actually this simple. They did screen test for people. Two of them, of course, were Julia Stiles and Heath Ledger. And the other two were Josh Hartnett and Eliza Dushku. Oh, Hartnett makes sense, too. I know.

It makes a lot of sense. I love Josh Hartnett. He kind of plays. He's got the slutty little bangs in the faculty. He has Courtney Cox's haircut from screen three in the faculty. And that's a great, great 90s teen movie that features a lot of the other future movie stars and whatnot. It does. I love Josh Hartnett. He doesn't, I don't think he brings the fun in the same way that Heath Ledger does, which you need in this movie.

What do you think, Mary? Where do you stand on that, Josh Hartnett? I love Josh Hartnett. I had a teacher, my freshman year, that looked like. Josh Hartnett that I had the biggest crush on? Wait, I did too. Was it just the unibrow? Was it just they had a little bit of unibrow? Because that's what mine was.

Let's all remember Tommy Lee Jones was the OG. And then Josh Harton stole it from it. It didn't hit as hard, though. I never tried harder in a class because I had a crush on my teacher. But I just feel like Heath Ledger, he's like light and airy and carcinatic and such like a natural. I feel like you walk into a room and he starts talking to you and you just get like enveloped by him.

And it sounds like that's what happened. as he was casted. I also don't remember him having, I really noticed, like, his freckles in this movie. Yeah. And there was something, like, young and innocent about seeing the freckles that I love, too. He's just charming, all well-rounded.

And he's got, like, his look with the hair. He's got a Jim Morrison vibe. I think it's something to it that fits Seattle in kind of a throwback way. He feels, like, heart-knit, I think, would feel more grunge. And, like, sexy. Yes. And I think that he,

is a little bit more charismatic that you want to talk to him. Like, he gets cuter the more you talk to him. Hartnett has a darkness that's really great in some of his roles. I really love it. Split. Shout out. Serial killer, Josh Hartnett. But not split.

What's the movie? Not split. What was the one? Trap. Which didn't feature enough trap music. Anyway. And he took such a long pause. He did.

Like, he didn't do a movie for, what, like 20 years? No, 10. Like, 10, like, 10. Like, lucky number 11. But that was him just saying, I don't want to be a part of Hollywood. And, like, he went to be with his family and I believe moved back to Minnesota. And, like, I know someone who knew him through mutual friends and just said he was, like, the loveliest guy who just had it. Like, he didn't want to do it for a little while. And so that was entirely his choice, which is, like, also pretty badass. So when it came time to film, they'd initially planned to shoot just a first.

few exteriors in Seattle, you know, bring the actors up for a week, whatever, five days, and then film everything else in L.A. But when Gil Younger saw Stadium High School in Tacoma, Washington, he was like, record scratch, we're filming the entire thing here. They were only three weeks away from filming and had to prep basically the entire shoot with that location change, which I'm sure his location manager was thrilled about. Some of the cast was stoked to be spending the summer in Seattle. Joseph Gordon-Levitt was not one of them. He wasn't happy about the last minute's which meant he'd be away from his friends for the whole summer. Because he's obviously an L.A. kid.

But this pivot also created a very close-knit vibe amongst the cast who all stayed at the same hotel. Apparently, they all had to be moved onto the same floor even because all the other hotel guests were like, please, please, it smells like weed. They're partying until three in the morning every night. You have to move them. I think Stadium High School was originally a hotel. It looks like it. I mean, it's beautiful.

Was there some romance going on behind the scenes? Well, eventually there was. Julia Stiles and Joseph Gordon-Levitt did actually date coming off of this movie. I believe that's the only relationship that generated from this. And they dated for a bit. Did you hear something else, Mary? So I think there might have been a little love triangle between JGL, Larissa, and Julia Stiles. I think you're right.

Okay, so I knew that he dated Julia Stiles briefly on the set of this, but I think he kind of like hopped from one sister. to the other after that and then dated Larissa Olenic. Okay, phrasing also not real life sisters, just to be clear. I'm just saying. All right, Mary with the gossip, very good. So another fun fact, apparently Heath Ledger showed up carrying a didgeridoo

and would play it frequently at the parties. It sounds like he was like the life of the party and everybody sort of rallied around him. Now, principal photography took place the summer of 1998 from June 8th to August 6th, all over Seattle, Tacoma, Washington. So you're wrong, Chris. It was primarily Tacoma. Oh, I didn't know it was primarily Tacoma. Because they do shoot in Lake Union on the paddle boats.

They do. Gasworks is obviously Seattle. Lake Union, Seattle. Carrie Park is Seattle. Yeah, I don't think they ever offered hand-throwing paintball at Gasworks, but I don't know that. That's definitely set up. That was like my dream date. I know. This moment. I mean, like... Paint throwing? This is like every girl's... Okay, I mean, I guess if it's Heath Ledger that you're throwing the paint with, sure. It's so fun. The realistic version of that is the snowball fight in Dumb and Dumber, where he beams her with the snowball.

Like, let's be honest. The guy goes too hard, yeah, probably. Yeah, exactly. Probably. But fun fact, Chris, producer Andrew Lazar rented a house on Mercer Island for the duration of the shoot. Oh, wow. Well, hometown.

Yeah. I also think that movies need to bring back this, like, montage, like, listen to an entire song and create, like, romance. scene. Like, I feel like all these 90s movies had these moments of like, we had the best time and they go out for like a full day date and have this great soundtrack to go along with it. And we're missing that from movies now. Yeah. I know. Bring back the montage. Gordon Levitt said we all really loved spending time with each other on that movie. While we were shooting, we all genuinely hung out all the time. That doesn't usually happen in my subsequent experiences on film sets. There was some kind of chemistry between that whole group of people, and I think when that happens, it shines through. Now, when McCullough and Smith visited, they would party with the cast, which apparently included piling everyone into a stretch limo and taking them to strip clubs, which, as our researcher pointed out, probably would not have flown if they were guys.

Chris, any top-notch Seattle strip clubs to shout out on the pod? There's one that David and Troy went to a couple times that they took me to. It was the one time I went to a strip club. I can't remember what it was called, and it was kind of a bummer, but it was a funny story because one of our friends was really drunk. And it was his last night before he was going to college. And so he proceeded to, we didn't know that, actually. And he kept going to the ATM and overdrafting his debit card.

Oh, my God. And ended up spending hundreds of dollars he didn't have. We took him home. I was the designated driver. I was sober. We took him home. He stumbled out of the car. And then somebody said, I can't remember who.

I didn't see him go into the house. And we were like, no, he must have gone. And they said, no. And sure enough, we all went up, he had failed to get his key in the door and he had gone to sleep in the bushes outside of his house. Oh, my God. We got him inside. Turns out he was supposed to go to college the next day and hadn't packed yet. So his mom, who's a badass and a hard ass, sent him to college with no clothes for like the first months.

And so he had to just wash his one set of clothes every other day. before he got close from his mom. I will not say his name. Well, you know, I've been to a lot of strip clubs. No, I've been to just the two in L.A. that are like really good. Jumbos, clown room and Cheetahs. I don't think Jumbos is a strip club.

I wouldn't call it a strip club. I mean, it is an entertainment venue, I would say. Mary, if you ever in an L.A., there have been Jumbos clown room. You should go. There are clowns, a lot of them. Check it out. It's great.

I used to live around the corner from it. I loved it. All right. So a couple of fun. about the filming. Andrew Kagan reportedly didn't know how to draw a penis on someone's face. I don't know what that means. So David Krumholtz said he instructed him on how to do it. Krumholtz said, in a way, I kind of conducted my own penis drawing on my face. I think he means like, where do you put the various parts, right?

Yes. That you aim it. I got you. Yeah. And also according to Andrew Kegan, apparently Larissa Olenick did actually punch him in the nose in the take that's in the film. She got him a little bit. I believe it. Yeah. I don't think it was like bad, bad, but she clipped him. Now, let's talk about the table dance scene. So do you know anything about Julia Stiles playing drunk in this sequence in this movie? Because remember, she's 17.

Yeah. I heard that she asked Heath Ledger, like, I've never been drunk before. Give me some tips. And he gave her some tips. And she got up there and had the time of her life. And that was quite. impressive if you ask me. I agree. So yes, he was sort of guiding her on how to be drunk, which is funny because he also is not 21, although I guess he's Australian. Hey, point of order for

our Australian friends. Isn't their age of drinking lower? Okay, fair. Point of order on Chris. I wasn't saying because they drink. I think it's because the drinking age is lower, but I'll double check that. I thought you were just saying because they're Australian. No. They're belligerent. But it is funny because Younger was actually good friends with Paula Abdul. So he was going to have her choreograph this table dance scene. And he mentioned that to Julius Stiles. He was like, I'm going to have a big choreographer come do this. And Julia Stiles is like, that's fine, but I can dance.

I'll just do this by myself. And he was like, okay. And let her get up there. And she said, quote, I would never have the guts to do that now. I'm glad somebody got that on film. I mean, I love dancing, but sort of provocatively on the table, I was pretty guileless at that point. I've also heard that that is what got me the part in saved the last dance. The director said to me that he had seen that scene.

and then realized I could do hip-hop, not just ballet. I love Save the Last Dance. I know it gets a lot of shit for that final dance that she does, which is a bit funny in retrospect, but she is a really good dancer. She is great in this moment. I'm so glad they didn't choreograph it because it looks good, but it looks real.

Yeah, it looks like a high school kid could do that. It's just so impressive. Like, she's a 17-year-old girl to have the confidence to go up there and do this dance. And then, I mean, the end of the end. of the movie. It's also a stunt. Like, she's above, she's on a table,

she's above a bunch of people. She could fall off. Which looks really good, by the way, when they have her bonk her head. Also, shout out to Julia Stiles for all of her falls in this because she really goes for it. There's, like, no holding back.

And every time I'm a little worried Heath Ledger is not going to catch her. Yeah, when she falls off the swing and he catches her, that was a great one. She goes, like, all the way back. Yeah, I could never do that. I would be way too scared. So in terms of Heath Ledger's serenade,

which obviously is one of the greatest parts of this movie. The first song they had in the script was, I think I love you. And then they changed it to, I touch myself, which would be a different vibe. And it was actually Heath Ledger, who was like, I don't think this is romantic enough. And he chose the Frankie Valley song that's in the movie, which obviously was a better call. I feel like I touch myself feels like older people making a choice for high school kids as opposed to, you know what I'm saying, as opposed to letting them choose what they would do, you know? Yeah.

Because what would be embarrassing to him is doing the crooner song. But it's also what makes it great and endearing. So it feels true to the character. Also, apparently it was like fully choreographed and Heath Ledger said, I just made it sloppy. He was like having so much fun running around. So funny. When he spanks the security guard is my favorite part.

Yeah. It's so funny. But he apparently, like the guards were having so much trouble running after him that they were afraid one of them like was about to have a heart attack because they could not keep up with Heath Ledger running around the bleachers. And he's 19. I'm like, I'm in decent shape for an almost 40-year-old. I could never keep up with a 19-year-old.

That's insane. No, don't even try. No. And then, of course, there is the infamous poem scene where she reads the reasons. I don't even hate you. Not even a little bit. Not even at all. That was not written for her to cry.

And when they went to film that scene, they did it in one take. She just started doing it. And Younger was like, this is amazing. We don't need to do this again. I almost wondered, not that it was one take, but it felt, she felt so natural and in command. And it really felt like she just unexpectedly broke at a certain point. And it's really phenomenal. It's a phenomenal scene.

She does such a good job. That felt true to high school, you know, the way that you could get raw, you know, unexpectedly in front of people. I really love that scene. Well, and she also said this, which I really appreciated, that Heath Ledger is an extremely generous scene partner in that moment. Because if you watch his reaction, it's very small. He's just listening to her and watching her. And she said that, you know, often in her experience, when one actor is crying and having a bigger moment, the other actor feels like they have to match that with the same kind of emotion. And he didn't do that. And apparently it's because he said, you know, this isn't about me. Like, this is your moment in this scene, in the spotlight. And I just think that's a really lovely. That's a very generous scene partner. And it's really nice when they pan to his reaction. I feel like it's great.

They had such great chemistry the whole entire movie. You could just feel it between them. Was he always in the class? I felt like... He walks in at the very beginning. He walks in and says, what did I miss? And then she says the thing about, like, you know, whatever she says. And he says, good.

And then leaves. Shout out, Daryl Mitchell. as the teacher. He's really funny. Also great in Galaxy Quest this same year, one of my favorite films. He's so funny.

I love when she genuinely likes the assignment and he says, get out of my class. Get out of my class. I really liked him. Just as the one black teacher at this school

and he's dealing with all these white kids. I really liked it. I did too. I don't know. There was just something about his character that felt it made the movie a little more honest in a great way.

I really like his character. He's very funny. The fact of, that he checked her, like on some of the, you know, the stuff that she's complaining about, and he's like, I know it must have been hard for you growing up, upper middle class white woman. And then the rostic is, say it's man. Don't even get me started on you. I also love it so meta, like, because I feel like an English teacher could show this movie to their class and then read the book along with it.

Yeah. Which, as a former teacher, I would like to do something like this. Yeah. I didn't know you were a former teacher. Oh, yes. I taught for 15 years and I taught third grade in kindergarten. Oh my God. I could literally never.

I could never do it. So kudos to you. Thank you. So when it came time to shoot that final bonkers helicopter shot, Disney had told younger that they loved what he was doing with the movie, but not that much. They did not okay the budget for this. But when the line producer came up to him and asked if they had approved it, something came over younger and he said, Yep. So they went ahead without Disney's approval for the budget to get this. And according to the lead singer of Letters to Cleo, Kay Hanley, it was really terrifying. It looks horrifying. I could never do it. She was like, they told us this is a helicopter shot. It costs $500,000 every time the helicopter has to take off. So don't fuck this up. So she's scared to death on the top of this building. And she said it looks, they see the helicopter coming. And then it looked. like it was like dive bombing them, which if you watch, it does like four times. So she's like about

to pee her pants and just has to keep going. And they do an amazing job. It's so crazy now you would just throw up a drone and it wouldn't be a thing. I know. I know. Or they just do it on a soundstage and replace the background, you know, too. But yes, a drone certainly. Yeah, it's a full blown helicopter just swooping up in their faces. I would barf. I could not be on the top of that building. One other fun thing apparently, and you can see this if you watch it, when Miss Perky says the same old shit for brains and flips off the kids behind her at the window at the very beginning, if you watch her mouth, watch it again,

it looks like annoying orange. They had to change it because originally she said fuck. So if you watch it, her mouth is like, like not matching her face at all. Another Galaxy Quest at the end with Sigourney Weaver. Well, fuck that, which it's to, well, screw that, you know, at the end. Yeah, yeah. All right, 10 Things I Hate About You premiered March 31st, 1999 to mostly positive, though more mixed reviews than I remembered.

And a decent, though again, not as big as I thought box office. It took home around $53.4 million, which again is very good. If the budget was $11.5 million, that's great. But part of the reason it didn't become as big a smash hit as we maybe remember it was it came out the same day as what movie, Chris? March 31st, 1999. Would it be Blair was Blair Witch March 31st? No, that was earlier. That was January. March 31st, 1999. It would spawn an entire subreddit genre. An entire subreddit genre. Are you going to take the blue pill or the red pill? Oh, the Matrix was, that's right. March 31st, 1999. Yeah. I forgot about that. Yeah, Matrix. 99 is such a good year for movies. It's so good. Sixth, August, Phantom Menace, say what you want about it in November. Like this, you just, you.

They were movies every quarter. Lizzie's face melted like a crayon and the hot sun. Well, the Matrix definitely stole a massive amount of glory from this. Of course. And The Matrix was also a movie that high schoolers, especially I can say from experience high school boys, well, I was only 10. But it was, we were obsessed. Yeah. We just thought like, this movie is going to get repurposed as a toxic male sort of symbol.

My God, you were right. Yeah. Now, of course, it was nominated. for 17 Choice Awards. It served as the breakout for Julia Stiles, Heath Ledger. So many people in this movie really broke out after it. But it really did grow in popularity after it came out. Mary, you mentioned this, but the rentals on this did incredibly well. And in the years since it was released, it's made the list of many best teen movies, rom-coms, best 90s movies, something I don't think anybody really expected it would do when it came out. Now, given the long-term success of it, of course,

skill younger returned to the 10 Things Cinematic Universe once for a never-released film called 10 Things I Hate About Life, starring Evan Rachel Wood, that was a disaster. It was never finished. Oh, wow. There is an ongoing lawsuit surrounding Evan Rachel Wood's departure from production. She claims she was never paid because the production company ran out of money. It's a huge mess. There was also a very short-lived TV series. And in 2025, Younger said he wanted to return to the franchise with not one, not two. but three, ten things I hate about you movies covering everything from dating to marriage. We don't need them.

No, we don't. This is perfect. Yeah. You don't need to do anymore. I also feel like we're missing what made it great, which the title's fun. Don't get me wrong. The poem's great at the end. But what made it great was it captured a feeling in a moment in time.

And also, these young actors, it's not really the property. It's we want to see Heath Ledger and Julia Stiles and all these people. Well, and the story was good. I agree. The story's good. But it's not a franchisable. story engine in any way. Well, you know who agreed with you is the screenwriters, who did not return for any of the reboots under Younger's Watch. But in case you don't know, they did go on to write some of

the greatest rom-coms of the 2000s, including Legally Blonde, The House Bunny, She's the Man. They co-wrote Ella Enchanted. Just throwing this out there to say, I think maybe they knew what they were doing a little bit more than they have gotten credit for in some of these oral histories. No, I think they totally knew what they were doing. They're great. That is a great. run of screenplays. And you said it was their second screenplay together. Yes. But for one of them, it was their 10th screenplay. Yes. So, and the other one was a script reader and had been writing coverage, writing her own work and poetry and whatnot. So it, I think these were two very smart writers who did a very tricky thing in adapting Lizzie's least favorite. I mean, that's saying something.

They took your, one of your least favorite Shakespeare. One of my least favorite comedies, for sure. And they turned it into maybe one of your favorite teen movies. It's true. That's, that's, I would say they improved on the source material, dare I say. So they have some really great rom-coms in the pipeline. Keep doing what you do best, ladies. I can't wait to watch them. And, of course, there is a Broadway musical in the works with score by Carly Ray Jepsen and producer Ethan Griske

and a book by Jessica Wong and Lena Dunham. I'm excited for that. That could be really good. Yeah. But of course, any reboot would not include Heath Ledger, who passed away in 2008 at the age of 28 from an accidental drug overdose. Now, David Krumholtz grew very close to ledger on set,

and he had this to say in the New York Times 20 years later. Toward the end of his life, I reunited with him at a time when we were both quite vulnerable in trying to recover from some stuff that was haunting us. I had an opportunity to tell Heath how much I loved him and sort of try to help Heath. He had become so famous, and his life had become so crazy, that in the moment when I could have said something, I didn't, even though I thought it. It's a big regret I have. To fans, he's a movie star that died.

to me he was flesh and bone, soulful, sweet, and I know for a fact he was in recovery prior to his death. I just want people to know there was a suffering individual there who couldn't have been a lovelier human being. I prefer to remember Heath as a 20-year-old kid doing his first American lead

with a big giant Cheshire Grand Smile on his face, taking charge as the leader of the group like any good ensemble leader should. Aw, that's tough. It was great. Carmel and I were remarking that we forgot that he passed away within a decade of this movie. And so what to me felt weird thinking about that was because I was 10 in 1999,

and then he passed away in 2008. So I was almost 20. Yeah, 19. For me, that was all of middle school, all of high school. And then my first, almost my first year of college, basically. And so it felt like a lifetime of having Heath, No, it was a meteoroprise. No, it was a media-or-up rise.

It was, and it was just narrow nine-year window, really, where you had, you know, the big touchstones, obviously, this. A nice tale. A nice tale for me. And then Brokeback Mountain and then Dark Night, amidst many other films, obviously. But yeah, it was such a brief window. Yeah. I mean, for him to go from, like, getting discovered on 10 Things I Hate About You, to doing this, like, profound movie, broke back Mountain, to his final movie. His final movie being the dark night is truly insane.

I'm curious, what is the year gap between, when is Brokeback Mountain? 2005. That's crazy. Six years between this and Brokeback Mountain, he just, like, he went nonstop. Skyrocketed. That was the one that said Keith Ledger's serious actor. Yeah. Not that he wasn't talented.

Everybody knew this guy's a pop movie star, right? But Brokeback Mountain, if I'm remembering correctly, for both him and Jillenhall, I think. and to a certain extent and Anne Hathaway as well. It really put all of them on the map in that sort of prestige way.

Yeah, it helped get Anne Hathaway Devil Where's Prada as we learned in that episode. Her performance, Merrill Streep saw her performance on that. Can I pivot and ask Mary a question? Yes.

Because she is our reality TV expert here. Yes. There's a really important reality TV moment in this movie on television briefly. Real World. Yes.

Yes. When they throw the fish and yes. Did you watch Real World Seattle? And I believe that was the first season of the real world. No. Maybe it's the second. New York is the first one, right?

New York. And I think they had San Francisco. No, Seattle was a little bit farther down. Oh, was it? Okay. That was why I'm asking. That was like Irene was on that season and she had Lime disease. And she got into a fight with Brad.

Why do I know this, you guys? Lizzie is just laughing at people with Lime Descent. No, I'm not laughing. It's just that that being her defining characteristics. No, Brad was San Diego. Sorry. Irene got into, like, she ended up leaving. Didn't she get into a fight?

I don't know. This is in 1999 or 1997. I mean, I was only born in 1985. So why was I 12 years old watching the real world Seattle? Oh, that's why I was going to ask. You knew what you love. Yeah. It is, yeah, I was also not allowed to watch the real world.

I was allowed to watch Die Hard many times, but I couldn't watch the real world. Okay. They lived on. Pier 70 of Seattle, Washington's Elliott Bay. Because what was happening, the lights in the house were really affecting her with her disease. Oh, no. Okay, now I look like a huge asshole for laughing. I was not laughing at her or at Lyme disease.

It was, I was laughing at you for qualifying her as having Lyme disease. She had like the Michael McKean condition in Better Call Saul. Oh, no, that's terrible. Response to. I know what you're saying. Yeah. Okay, well, now we have to go back and, uh, rewatch Real World Seattle. All right, well, we like to end our episodes, Mary, by asking

what went right. And obviously, a lot went right on this movie. That's part of why it gets a featurette and not a main episode. But what would you say went right? I think what went right was the chemistry between Heath and Julia Stiles. I just think it was like magnetic. They had an amazing rapport. You could feel the love and the energy. And, you know, watching that as a teen, you wanted to feel that as well. You wanted to have a relationship like that. I agree. So shout out to the casting directors, because I think the cast of this movie is incredible,

and the chemistry is great. Chris, what about you? Okay. I'm going to give mine, because I'm going to say that one went to Heath Ledger and Julia Stiles, who I agree. And I think Julia Stiles is overlooked a little bit in retrospect. She's great. She also stepped away, I think, from movies a little bit.

She's so good in this movie, so shout out Julia Stiles. Okay. Can I give mine? to the father-daughter relationship in this movie. Yes, I love it. I think it's really good. I actually like that he is very honest and open with his daughters about sex. And it's not a conversation about morality or anything like that, although there's one

line that Bianca has that would not live today. Okay, that is acknowledged. However, him just saying, look, I don't want you to get pregnant when you're young and possibly not have the future that you want, but he's ultimately supportive of his daughters. and her going to Sarah Lawrence, for example. And I think the way that Larry Miller plays it is very fun and bleans just enough into the sort of put-upon dad, you know, trope that we all know.

But he gives it a lot of humanity. And at the end of the day, he realizes he doesn't really have any control over these, like, very smart, headstrong young woman in his house. And I really like that story, maybe just because I'm a dad to a little girl now. But I thought it was really nice. No, I loved it. I also just loved that he was a gynecologist. Yeah.

And that was where he was coming from. I love when he's like, you're going to wear the suit. Wear the belly. It was perfect. Yeah. And now watching it as a parent, I was like fully on his side of that very much. And I also, you know, I grew up with a single dad who I watched this movie with a lot. And I wonder if that's part of what he connected to in this.

My poor dad who had to take me to the mall to buy a training bra. And he was like, I will be over here. This woman will help you. But God love him. He did it. So shout out to Chip. And shout out to Larry Miller. I do love his performance in this.

All right, I'll keep mine very brief. I'm going to go back to Ralph Sal, the music supervisor. I just think this soundtrack is absolutely insane. And it really is burned into my brain in a way that... Favorite song? Now, well, don't do this to me now. Okay, I will say it's a tie between I love sexy boy by air, because that's actually just like a great song.

But I actually really love the Joan Arma Trading song, The Weakness in Me, that's in this movie, which I've never really heard anywhere else, and I'm not super familiar with a lot of her work, but I think it's a beautiful song. I loved it then. I love it now, and I love the placement of it in this movie. So shout out to Joan and shout out to Ralph. You really stuck in my craw. All right, Mary, thank you so, so much for being here.

Is there anything you would like to plug before you leave? No, thank you so much for having me. you guys. If you want to listen to my podcast, it's called Two Judgy Girls. You can find it wherever you listen to your podcast. It's great. You absolutely should. I love listening to you all. My news comes from you, Mary. All right. Thanks so much. Thank you, Mary. Thank you. Bye. What went wrong is a sad boom podcast presented by Lizzie Bassett and Chris Winterbauer, post-production and music by David Bowman. This episode was researched by Jesse Winterbauer and edited by H. Conley.