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1* AdaptationDisplacement: Viewers not old enough to remember the 1976 movie, much less the original book, probably consider this the definitive version of the story. Its status as a CulturallySensitiveAdaptation 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 MadeForTVMovie in 1995.
2%%* SugarWiki/AwesomeMusic: “Take Me Away”.
3* BigLippedAlligatorMoment: 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 ChekhovsGag.
4* CrossesTheLineTwice: "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.
5* EnsembleDarkhorse: Anna's ThoseTwoGirls bandmates Maddie and Peg provide a decent amount of humor, not to mention some good garage band music.
6* EthnicScrappy: Pei-Pei's characterization involves speaking in broken English and being presented as an annoying GenkiGirl - not to mention Tess refers to "Asian voodoo", which would be confusing African voodoo with Asian practices (the closest Chinese equivalent would probably be [[https://en.wikipedia.org/wiki/Chinese_shamanism Wuism]]). Still, Rosalind Chao does at least make her funny, and in fact she decided to take the role to honour her father, who had run a similar restaurant. 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.
7* FanficFuel:
8** It's subtly implied that Pei-Pei's mother has made other people who are arguing switch bodies before. Cue the fanfic writers.
9** What would've happened if Harry and Grandpa really ''did'' switch bodies at the end of the movie?
10* FansPreferTheNewHer: 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.
11* FanPreferredCutContent: Many fans of the film feel that the DeletedScene in which Tess punches Stacy in the face, breaking her nose in the process should've been kept in the film, given that it shows Stacy getting her comeuppance.
12* HarsherInHindsight:
13** The sequence of Tess-in-Anna having to fake playing the guitar brings to mind Lindsay Lohan's own infamous lip sync [[https://www.youtube.com/watch?v=iX_3qlxbp-I incident]] a few years later.
14** Creator/LindsayLohan's mother telling her to "make good choices", considering by the end of the decade she would become synonymous with the HardDrinkingPartyGirl FormerChildStar, and her mother was infamous for taking her to nightclubs while underage.
15** 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.
16* HilariousInHindsight:
17** Watch ''Film/HouseOfWax2005'' immediately after this, and once again you'll see Chad Michael Murray being thought a delinquent but he turns out to be a NiceGuy.
18** The subplot of Jake being attracted to Tess is also amusing to fans of ''Series/ScreamQueens2015'' - where Jamie Lee Curtis is a DirtyOldWoman sleeping with college students. The kicker? Chad Michael Murray appears in that too (though their characters don't interact).
19* JerkassWoobie: Anna. She's abrasive, rude, and is always at odds with her mother, brother, and her mother's fiance 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 [[spoiler: her mother snubbed him ''years ago in high school'']] and she's still hurt by the loss of her father.
20* {{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.
21* QuestionableCasting: The actors playing Mr. Bates and Evan (Stephen Tobolowsky and Willie Garson respectively) look so similar in appearance, down to baldness pattern and glasses that it could be a bit confusing for first-time viewers.
22* [[SugarWiki/HeReallyCanAct 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 ''Film/HalloweenH20TwentyYearsLater'' (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.
23--> '''Newsweek:''' "The most startling metamorphosis is Curtis' transformation from fading horror flick queen to dazzling comedienne. She goes on a teenage tear—tormenting 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 aging—with fiercely funny conviction."
24* {{Squick}}: Tess and Anna are so disgusted with the possibility that Anna will have to marry a man in his 40s, that Anna constantly [[AlmostKiss 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.
25* StoicWoobie: 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 fiancee acting cold towards him. But he doesn't complain or even talks about it until his little speech towards the end.
26* TearJerker: 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".
27* TheyWastedAPerfectlyGoodPlot: The ending of the movie has Harry and Grandpa fighting and Pei-Pei's mother giving them a fortune cookie. This could've been a perfect opportunity for a HereWeGoAgain! ending. But nope. StatusQuoIsGod.
28* UnintentionalPeriodPiece:
29** All the gizmos Tess puts in her purse and has to juggle on a daily basis would definitely not have been included had the film been made in TheNewTens. Even just entering the next decade, she would have had a single smartphone to replace all of it, which might have made the theme of her workaholism keeping her away from her family harder to convey.
30** Anna's band is also quite reminiscent of the PopPunk and PopRock styles that were cool during the early 2000s. Even her whole outfit is a dead ringer for Music/AvrilLavigne and her style at the time.
31** The House of Blues venue featured in the movie has moved to a different, though close, address since the movie was made.
32* UnintentionallyUnsympathetic: While Harry is just a child, and Anna learns that he actually worships her, and only fights with her for fun, some of things he does are extremely over the line - taking his friends into her room and reading her diary aloud, as well as playing with her underwear. Tess likewise never seems to punish or reprimand him for this.
33* ValuesDissonance: Anna in Tess' body tries to make Harry walk 20 blocks to school as payback for what he did to her earlier. While still hilarious due to her unsympathetic response to his concern that he might encounter bullies, any parent nowadays who lets their kid walk that far to school unattended would be facing a visit from CPS at minimum.

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