For a whole generation, watching high school sex comedy American Pie (1999) was one of those seminal teenage experiences.  A modern update on raunchy National Lampoon-style movies from the 70s and 80s like Porky’s (1981) and Animal House (1978), many of its most quotable lines quickly found their way into the popular lexicon. Everyone was talking about the things they did “one time, at band camp” and pointing out that their friends’ moms were MILFs. It really raised the caliber of the public discourse.

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It should, therefore, come as no surprise to find that American Pie hasn’t aged particularly well. However, in the interests of fairness and balance, this list doesn’t focus entirely on the movie’s many flaws. So not only do you get 5 things that have aged poorly in American Pie, but you also get 5 that still hold up today.

Aged Badly: Stifler

Steve Stifler (Seann William Scott) was meant to be a douchebag, even back in 1999. But whereas in 1999 he was a raucous jock whose antics were played mostly for laughs, viewing him through a 2020 lens makes him seem downright psychopathic.

In one of his first scenes in the movie, Stifler gets pretty aggressive in his attempts to cajole a girl into having sex with him. And it’s also Stifler’s idea to secretly film Nadia (Shannon Elizabeth) when she comes over to Jim’s (Jason Biggs) house later in the movie (and if you think that gag has aged well, you’ll soon be disappointed).

The movie tries to have its pie and eat it too by also making Stifler the butt of many of its gross-out jokes, but he’s still portrayed as a laddish antihero when he’s really just a creep.

Held Up: Oz

At the other end of the jock spectrum is kind-hearted Chris “Oz” Ostreicher (Chris Klein). Commending a guy for simply not being a jerk is faint praise, but in a movie with few redeeming qualities by modern standards, Oz does stand out as a genuinely likable dude.

Although he originally joins the school choir just to sleaze on Heather Gardner (Mena Suvari), Oz soon discovers that he is a talented and passionate singer. His narrative arc from hormonal sports-loving jock to sensitive new age guy shouldn’t earn any undue plaudits, but it still sends a positive message in a movie where those are in short supply.

James “Jim” Levenstein has been lusting after exchange student Nadia, and so when she asks if she can come over to his house to study one night he is overjoyed. But the whole thing turns decidedly icky when she reveals she’ll be coming straight from her ballet class and will need somewhere to change. Jim offers his room, and Stifler convinces him to set up a webcam to film her in the act.

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The movie makes a lame attempt at moralizing by having the scenario backfire on Jim when he is caught on camera prematurely ejaculating, earning the ridicule of everyone at school. But the fact that it was possible – even in 1999 – to have the hero of your movie film a naked woman without her consent and play it for laughs is pretty staggering.

Held Up: Jessica

Jessica (played by Russian Doll’s Natasha Lyonne) is one of the movie’s few bright spots. She’s a genuinely funny character with the sardonic wit of a post-grunge Daria-esque 90s teen. But Jessica is also sex-positive and a great support for her friend Victoria Lathum (Tara Reid), who is weighing up whether she is ready to have sex with her boyfriend Kevin Myers (Thomas Ian Nicholas).

In one of the movie’s few honorable acts, it never slut-shames Jessica or passes any real moral judgment on her character. Instead, she’s presented as a normal girl in her late teens who just so happens to be sexually active. So kudos, American Pie writers.

Aged Badly: The Pact

The driving force behind the plot of American Pie is the pact made between the film’s four hormonal protagonists: Jim, Oz, Kevin and Paul Finch (Eddie Kaye Thomas). They each pledge to help one another in their individual quests to have sex before prom night so that they won’t graduate as virgins.

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While the pact itself is pretty skeezy, it’s really the language the characters use to describe it that makes it so problematic by 2020 standards. In an age of incels, if you ever hear a horny teenager proclaim that he is “fighting for every man out there who isn’t getting laid when he should be!” the first thing you should do is head for the nearest exit.

Held Up: The Amicable Breakup

Defenders of American Pie will claim it’s a classic coming-of-age story depicting the growth of its protagonists from petty, sex-crazed teens into respectful and well-rounded adults. This ignores the obvious fact that no one learns anything and they all still suck at the end (except for sweet Oz).

However, at least one interaction late in the film shows that a degree of mutual respect exists between at least two of the characters. After Kevin and Vicky finally have sex, she breaks up with him, citing the impossibility of them continuing their relationship while attending different colleges. To his credit, Kevin accepts her reasoning while acknowledging the love they still share for one another. It’s not like it’s the end of Before Sunrise (1995) or anything, but it’s sort of nice.

Aged Badly: Stifler’s Mom

We can all agree that Jennifer Coolidge is a goddess, but her turn as the Mrs. Robinson-inspired Jeanine Stifler is morally hazy. In 2020 we’re all for consensual sex in all its various forms and permutations, but when it involves a potential minor – even if he does wear tweed and act like a 50-year-old college academic – it’s still a bit iffy.

For some, Stifler’s mom is a no-holds-barred cougar feminist icon. But for others, she’s a bad news headline waiting to happen.

Held Up: Jim’s Dad

Jim’s dad (played by Eugene Levy) is a bit “hands-on” in his parenting style (giving your teenage son a lesson on the nuanced differences between Playboy and Hustler centerfolds may be a bit misguided), but there’s never any doubting the earnestness behind his awkward attempts to help Jim navigate the sexual minefield of high school.

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And his delivery of the line “we’ll just tell your mother we ate it” after coming home to find Jim having sex with a freshly baked apple pie is still genuinely funny.

Aged Badly: Attitudes towards women

This list has already covered the “pact” and “the webcam incident,” but it’s still worth reiterating just how gross the portrayal of women is in this movie. Sure, Jessica’s pretty great and Alyson Hannigan’s character Michelle Flaherty, “from band camp,” has her moments, but on the whole, the movie doesn’t really care much about their feelings or autonomy.

Take the fallout from the webcam incident. Jim is humiliated in front of everyone, but exchange student Nadia is literally expelled from the plot for her sins and sent back home to Slovakia. Jim seems to feel no guilt for his part in it; instead, he’s more concerned about the impact this might have on his chances of finding a date for the prom.

Held Up: Jessica & Tom’s advice

When Kevin is attempting to win back Vicky, he seeks sexual advice from both Jessica and his older brother Tom. To their credit, both Jessica and Tom only provide their advice to Kevin once he’s stated that he won’t use it to take advantage of Vicky, but "because it would be nice to know that she enjoyed things as much as I do". That's a pretty nice little didactic moment on humanization and sexual generosity, which is more or less undercut by everything else that happens in the movie.

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