- 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.
- 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.
- 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.
- "Funny Aneurysm" Moment: Lindsay Lohan's mother telling her to "make good choices."
- Harsher in Hindsight: Lindsay Lohan's mother worried about other people being bad influences on her...
- Hilarious in Hindsight:
- Knowing that it's Gibbs from NCIS playing Ryan, when Mark Harmon talks, you listen.
- 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.
- 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).
- 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.
- 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.
- Values Dissonance: The scenes with Pei-Pei make quite a few Asian Speekee Engrish jokes at her expense. These only got a couple of mild criticisms, but would probably not fly today; Pei-Pei and her mother don't appear in the 2016 musical.
YMMV / Freaky Friday (2003)