- Adaptation Displacement: Viewers not old enough to remember the 1976 movie, much less the original book, probably consider this the definitive version of the story. Society Marches On contributed to this displacement, as this version allowed the mother to have a job, leading to more possibilities for jokes the original didn't get to make due to the mother in that version simply being a housewife. This is even the second remake of the story, another being a Made-for-TV Movie in 1995.
- Big-Lipped Alligator Moment: There's a random comedy moment in the supermarket when Tess is talking to a patient of hers on the cell phone - assuring her she's a smart, strong, beautiful woman who doesn't need a man to complete her. The lady at the deli mistakenly thinks Tess is speaking to her and burst into tears, saying "thank you". It's rather random, which explains Tess's confused reaction. It's possible that Elizabeth, the patient named in question, is the incomprehensible woman that Anna-as-Tess has to suffer through the next day, however, making it a likely Chekhov's Gag.
- Crosses the Line Twice: "I don't want to get married at fifteen! I'm not even sure it's legal!" - the Squick present in the idea that Anna may have to marry Ryan becomes hilarious when it's put like that.
- Ensemble Dark Horse: Anna's Those Two Girls bandmates Maddie and Peg provide a decent amount of humor, not to mention some good garage band music.
- Ethnic Scrappy: Pei-Pei's characterization involves speaking in broken English and being presented as an annoying Genki Girl - not to mention Tess refers to "Asian voodoo", which would be confusing African voodoo with Asian practices (the closest Chinese equivalent would probably be Wuism). Still, Rosalind Chao does at least make her funny, and she does get a moment where she chews her mother out for causing the plot in the first place. Tellingly the musical, which takes more than a few cues from this movie, doesn't include Pei-Pei or her mother.
- Fans Prefer the New Her: Tess is repulsed by the makeover Anna gives her - "I look like Stevie Nicks!" - but to a lot of viewers, it's a vast improvement over what she was wearing beforehand. It helps in-universe that Pei-Pei, Ryan, and Jake take a fancy to her makeover.
- "Funny Aneurysm" Moment:
- Lindsay Lohan's mother telling her to "make good choices."
- Anna-in-Tess's talk show appearance has the speech about adults acting immaturely - "and quality time with your kids? Quit bugging them, leave them alone, they like it" - considering Lindsay Lohan's own very public falling out with her mother.
- Harsher in Hindsight:
- Lindsay Lohan's mother worried about other people being bad influences on her...
- The sequence of Tess-in-Anna having to fake playing the guitar brings to mind Lindsay Lohan's own infamous lip sync incident a few years later.
- Hilarious in Hindsight:
- Knowing that it's Gibbs from NCIS playing Ryan, when Mark Harmon talks, you listen. That's not getting into Curtis' role in the aforementioned show as Dr. Ryan, who also happens to be a psychologist. On the other hand, Gibbs and Ryan's story didn't have as happy an ending as Tess and her Ryan's.
- Watch House of Wax (2005) immediately after this, and once again you'll see Chad Michael Murray being thought a delinquent but he turns out to be a Nice Guy.
- Chad Michael Murray also starred as the love interest in A Cinderella Story, opposite Lindsay Lohan's rival Hilary Duff - who had really lobbied for the part of Anna in this. For bonus points, Julie Gonzalo plays the Alpha Bitch and makes the main character's life hell in both films.
- The subplot of Jake being attracted to Tess is also amusing to fans of Scream Queens (2015) - where Jamie Lee Curtis is a Dirty Old Woman sleeping with college students. The kicker? Chad Michael Murray appears in that too (though their characters don't interact).
- Lindsay Lohan being terrorized by an Alpha Bitch is also amusing in light of her next film with Mark Waters - the famous Mean Girls, featuring Lindsay's character devoting the run-time to Backstabbing the Alpha Bitch.
- Jerkass Woobie: Anna. She's abrasive, rude, and is always at odds with her mother, brother, and her mother's fiancee despite the fact that he wants her to like him. But it's made clear that the reason she's the way she is due to bullies, a teacher that hates her just because her mother snubbed him years ago in high school and she's still hurt by the loss of her father.
- Narm: Some of Anna's lines in the first half of the film sound like they were written by someone with only a vague idea of what teenagers would actually say. Notably her "you're ruining my life" when Tess tells her she can't get a nose ring. Tess even mocks Anna for it when they switch bodies.
- She Really Can Act: A lot of critics felt that Jamie Lee Curtis had been fading out of the limelight, with her most notable previous credit being Halloween H20: Twenty Years Later (which was banking on Halloween nostalgia). With this film, she went in a completely different direction to her normal roles and impressed everyone with her over-the-top antics that proved Actually Pretty Funny.Newsweek: "The most startling metamorphosis is Curtis' transformation from fading horror flick queen to dazzling comedienne. She goes on a teenage teartormenting Anna's younger brother (who wonders why Mom's acting so weird), getting down and dirty on a TV talk show where Tess is supposed to discuss her book on agingwith fiercely funny conviction."
- Squick: Tess and Anna are so disgusted with the possibility that Anna will have to marry a man in his 40s, that Anna constantly prevents Ryan from kissing her. They also don't take kindly to the fact the boy Anna had a crush on has started to fall in love with a grown woman.
- Stoic Woobie: You end up feeling very sorry for Ryan throughout the whole film, considering Anna's utter indifference to him despite his attempts to connect with her. And when the switch happens, he spends the whole day suddenly having his fiance acting cold towards him. But he doesn't complain or even talks about it until his little speech towards the end.
- Tear Jerker: Anna-in-Tess's speech at the rehearsal dinner, where she speaks about her father and how the loss affected them. Her voice breaks as she says "he was a really great dad".
- Unintentionally Unsympathetic: While Tess is meant to come across as an overwhelmed and overworked mother who's out of touch with her daughter, a lot of her actions in the first act of the film make her seem callous at best and uncaring at worst. Anna is having problems at school, so Tess punishes first before trying to find out what the problem is (and her punishment is taking away the door to Anna's bedroom, declaring "privacy is a privilege") and dismisses Anna's claims that she's being bullied as teenage Wangst - when even if she didn't believe her, could at least warranted a meeting with the principal to find out more. Then there's the audition, which Tess simply says she can't go to because it's at the same time as her rehearsal dinner. The dinner is going to last for a few hours, the audition less so, and the location isn't even that far away ("half a block" according to Maddie) so it makes Tess seem even more self-centered to make Anna miss it. Granted, Anna didn't do a good job of explaining the situation, but Tess just rules against it anyway. It doesn't help that Anna's reckless decisions (the makeover and the talk show craziness) are seen as "cool" by people in-universe whereas Tess' actions, such as getting back at a mean-spirited bully in defense of her daughter's honor, are met with aghast at best and being called out at worst - since everyone assumes the respective person is doing them, it suggests that Tess is able to get away with anything.
YMMV / Freaky Friday (2003)