* DesignatedHero:
** The parents. In both movies, they were people who got divorced and, to make it easier on ''themselves'', decided that each would only get custody of one child and never mention the existence of their sibling.
** Hallie in the remake comes quite close as well. She initiates all the arguments (pulling Annie into the water, stealing her clothes), behaves like a spoiled brat in the isolation cabin and forces Annie to deal with all the drama surrounding Nick's relationship with Meredith because she wants to spend more time with her mother. And there's the fact that Annie is forced to both cut her hair ''and'' get her ears pierced, all Hallie has to do is change her accent.
* EarWorm: The original movie has "The Parent Trap" and "Let's Get Together," two of the first songs that Music/TheShermanBrothers wrote for a Disney movie.
* FridgeHorror: Exactly how many relatives were aware of what the parents had done and were forced to keep it a secret? Even the servants and staff knew and had to keep quiet about it.
* FanDisservice[=/=]FetishRetardant: The appearance of the Butler in the LindsayLohan version, wearing a Speedo.
** To be fair, he's ''not'' fat or ugly. It's just that for some Americans, there's something uncomfortable about a middle-aged or elderly adult in bathing suit typically worn by the younger generation.
* FirstInstallmentWins:
** The Hayley Mills version had three sequels, the last one coming just nine years before the Lindsay Lohan version. Anyone remember them? The third and fourth got hit especially hard; ''The Parent Trap II'' at least became bundled with the original on DVD.
** On the other hand, whether you're more familiar with the Hayley Mills version or the Lindsay Lohan version will probably depend a lot on how old you are.
* HilariousInHindsight:
** Dennis Quaid plays a father who just got divorced who's kids want him to get back with his wife. Seven years later, Quaid would star in the 2005 remake of ''YoursMineAndOurs'' where he plays a widowed Coast Guard with 8 kids who marries a widowed handbag designer (Rene Russo) with 10 kids. But this time, the kids' goal in that film is the ''total opposite'' of the twins' goal--They want the parents to ''split up!''
** When Lohan and Richardson are crossing the street "Abbey Road" style, parked nearby is a white, classic VW Beetle. Lohan's final film for Disney (so far) became ''Film/HerbieFullyLoaded''.
** Annie and Hallie being "punished until the end of the century" is funny when you realize that the movie takes place in 1998.
* SheReallyCanAct: Anyone who doubts LindsayLohan's capabilities as an actress needs to watch this film, stat.
* ValuesDissonance:
** The idea that parents who broke up in a divorce should get back together, no matter how much they fight is odd to 21st century society.
** Mostly avoided in the remake. It's mentioned that the main reason for the divorce was "we were both young, we both had stupid tempers" as well as Elizabeth technically not wanting to leave -- she expected Nick to stop her so they could make up but Nick believed she wanted to leave. Now that they've matured and sorted their issues out, they might fare better.
* WhatAnIdiot: Granted, everything had already gone to hell by that point anyway, but Meredith ranting she planned to ship Hallie and Annie off to Switzerland and telling Nick "It's me or them, take your pick" comes across as galactically stupid since they're, you know, his ''daughters,'' one of whom he clearly loves and dotes on, and the other who he hasn't gotten to see in years. Did she really think he was going to pick ''her'' in that ultimatum?
** Yeah, she did. That's the way narcissistic people roll.
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