Alternative Character Interpretation: If you want to be more cynical about Bianca's Heel Realization, you could interpret her giving Cameron the Big Damn Kiss as a convenient way to stop him from being mad at her. Or it could be genuinely wanting to make amends since a simple apology could be taken as manipulative. Or both.
Jessica Riddle's "Even Angels Fall" playing during the prom as Kat walks away from Patrick.
Letters to Cleo perform a very awesome cover of "I Want You To Want Me" over the end credits.
Crosses the Line Twice: Kat sneaking Patrick out of detention...by flashing the coach. The fact that this is a teenage girl doing so to an adult would normally raise eyebrows, but it's so hilarious that you don't care.
Draco in Leather Pants: YouTube channel The Take framed Chastity as this. As detailed in both their "The Best Friend Trope, Explained" and "The Becky Trope, Explained" videos, they paint her as a lonely girl who has to deal with Always Someone Better in comparison to Bianca (which is strictly head canon - Bianca is sought after because her father won't let her date). She's actually a False Friend who abandons Bianca at the party for Joey, laughs meanly at Cameron, and rubs it in Bianca's face that Joey only wanted her for the sake of a bet. She's arguably the closest thing the movie has to an Alpha Bitch.
Estrogen Brigade: With Joseph Gordon Levitt in the middle of his teen heartthrob phase, Andrew Keegan showing plenty of skin, and Heath Ledger's breakout role (and with a scene where he's walking around in tight leather pants) - it's unsurprising this ushered in puberty for many '90s/'00s girls.
Kat apparently has a photo of Jared Leto in her room. Coupled with Heath Ledger playing her love interest, she must have a thing for the Joker. And Joker (2019)'s Signature Scene is when the Joker dances on the stairs, and this film has a scene where Heath Ledger's character dances on stairs too.
Watch "O" right after this, which is another modernized Shakespeare play (in this case Othello) and stars Julia Stiles and Andrew Keegan. In both, him not sleeping with her is a plot point.
4 Years after this movie, Gabrielle Union would star in Deliver Us From Eva, another adaptation of The Taming of the Shrew, but this time being the shrewish woman herself.
Jerkass Woobie: Kat seems like a straight-up Jerkass but she's dealing with her mother's departure, an overprotective father and being dumped for not putting out.
Allison Janney as Ms Perky. Technically a Two Scene Wonder - but most of the fandom wishes she'd been in more.
Mr Morgan, the Cool Teacher who takes no shit from Joey (or indeed Kat) has only about five minutes of screen time, but is another memorable part of the movie.
If you're a scifi fan who can't put their finger on why Mr. Morgan looks and sounds so familiar, he was Tommy Webber in Galaxy Quest around the same time.
The most memorable scene is the one where Kat reads out the titular poem, wells up with tears (an unscripted Throw It In! from Julia Stiles), and runs out of the classroom.
Closely followed by Patrick singing to Kat on the football field, one of the most iconic Grand Romantic Gesture moments of the '90s.
Strawman Has a Point: Walter gets annoyed at Kat when she drives into Joey's car after he blocks her way, and he has a point in that she intentionally damaged two cars that he's likely going to have to pay for, and his insurance won't cover actions like that.
Kat discovering the bet is indeed quite a sobering moment, even if she's mostly snapping at Patrick. She believes he never cared about her and just saw her as a means to financial gain, while he's trying to convince her he does love her. She walks away, and you can then see Bianca appearing behind Patrick - feeling guilty for what her sister has just had to experience. Having "Even Angels Fall" playing over the scene doesn't help.
The scene where Kat read the poem at the top of the main page in class. More specifically it was meant for Patrick. Kat starts to get tears in her eyes and cries as she's reading, and the camera goes to Patrick (Heath Ledger) and you see he got kind of upset too. That would be because the script didn't call for tears, but she actually started crying anyway. Most likely, that was also Heath's reaction to seeing her cry.
Testosterone Brigade: Larisa Oleynik playing a Girly Girl whose beauty is displayed in every scene, and Julia Stiles showing off a more tomboyish yet still incredibly alluring persona (and some gorgeous long hair) and a beautiful young Gabrielle Union - male moviegoers had plenty to enjoy.
Unintentional Period Piece: The film would qualify only for the clothes and casual use of the word 'retarded', but Kat is also a huge fan of Jared Leto and other characters reference The Real World and Dawson's Creek. The original script had many references to the Washington Riot Grrl music scene that was big at the time, but the film does still name drop bands like The Raincoats and Bikini Kill. Letters to Cleo feature prominently - one year before they disbanded in 2000. The Wild Teen Party comes about when invites are distributed via flyers instead of the internet, and Bianca and Cameron have to search Kat's room to find out what her interests are rather than just look at her social media. The poster for graduation even displays the slogan "Blasting into the year 2000".
Despite the Stratford dad being cartoonishly overprotective, lines of dialogue say that the mother just up and left - and doesn't seem to be involved in their lives at all. As he's also a doctor, he's likely in over his head trying to raise two teenagers on his own. And let's face it - Kat is not the easiest girl to live with. Mercifully he has a Heel–Face Turn by the end.
Patrick gets framed by the movie as having "embarrassed" Kat when he refused to kiss her after Bogey Lowenstein's party, and he's told by Cameron and Michael that he needs to make it up to her. However, at the time, Kat was drunk and was implied to not be in the right state of mind. As noted in Values Dissonance, if Patrick had kissed Kat in that instance, it would be seen as him taking advantage of her. Patrick arguably did the responsible thing in that situation when he refused her advances and told her "Maybe we should do this another time." Even before this, he's the one who was telling Kat at the party to take it easy on the alcohol (which she ignored) and later helped her after she bumped her head on the chandelier because he was worried she might have gotten a concussion. It doesn't help tha Kat had already vomited that night, and pragmatically, Patrick perhaps just didn't want to kiss a girl whose breath smelled like puke. Played with in that their advice is less 'You did the wrong thing' and more 'She feels like she embarrassed herself in front of you, here's how to make her feel better' — it's contrived, but also understandable that a closed off person like Kat would withdraw when feeling exposed after embarrassing herself.
'Retarded' is used casually by a couple of characters, as it was not widely considered a slur in the '90s.
While scandalously hilarious, you'd probably not get away with a scene in which a teenage girl flashes her coach being Played for Laughs.
It's also surprising that Kat gets annoyed at Patrick for not kissing her back while she's drunk. Her reasons are in fact more nuanced than Questionable Consent but it's a surprising plot point all the same.
While it's not entirely surprising that a sensitive guy like Cameron might be overly defensive about sounding gay, as it is generally sensitive guys who are labelled that way, with increasing awareness of how there is absolutely nothing wrong with being gay, his defensiveness can seem a little OTT by modern standards.
It's been noted that the English teacher snapping at Kat is an early example of criticizing the idea of 'white feminism' focusing solely on the problems of privileged straight white women over people of color, disabled people, LGBT etc. This can also be applied to how Biancaand Chastity are contrasted in terms of desirability within the story with the former only getting the Big Man on Campus only after the white Bianca is no longer available given how there is more serious attention to the disparity in beauty standard preferences towards Black women.
Kat herself is a very layered character who subverts many tropes associated with Tomboys or Straw Feminists - especially for the time period. Years later, people still point to her as a relatably unconventional female lead. Likewise, Bianca is shown to be quite deep and layered while being completely different to her sister - with her femininity not being shown as a lesser trait.
The Woobie: Cameron, particularly in the scene at the party when Bianca walks away from him...
The series contains examples of:
Badass Decay: Patrick is initially Shrouded in Myth but later intimidates Cameron into accepting delivery of a Snuggy for him.
Ensemble Dark Horse: Cameron and Bianca. The former due to being a Lovable Nerd and the latter to being much nicer than her movie counterpart.
Les Yay: Bianca and Dawn play this up in their webshow to get viewers. Walter is not pleased.
and "The Becky Trope, Explained"