5 Classic ’90s Movies That Are Actually Kind of Fucked Up

Feel free to use in your 90’s dissertation


Every time I see a Mrs. Doubtfire gif, I’m reminded that almost every loved movie made in the ’90s was at least low-key fucked up and no one really talks about it. It actually took a great deal of discipline to whittle this down to five per my editor’s guidance. (Although even I can admit that including every movie in the Mary-Kate and Ashley franchise would have been a little overkill.) It’s possible I’m about to embark on what will be the most cynical listicle ever written vis-a-vis ’90s pop culture, but I feel very strongly that someone has to do it.

Let’s start with the aforementioned heavy-hitter:

1. Mrs. Doubtfire


The gender politics in this movie are truly fucked. Poor Sally Field! All she wants is to be married to a person who respects her! Have a fulfilling career! Co-parent with someone who exhibits a shred of responsibility AKA does not bring live farm animals into the house without her consent!!! And yet her character is V shadily demonized for putting her foot down while her selfish, unemployed husband is characterized as an underdog worthy of our loyalty. Then, instead of, I dunno, getting his act together honestly, Robin Williams cons his way back into the family home by pretending to be a woman (offensive) thereby taking money from the single mother of his children (actual thievery). And the worst part of all is that it works.

Fucked up.

2. Big Daddy


Let’s pivot to another ’90s classic wherein an irresponsible, essentially unemployed white dude is forgiven of all sins because he’s “”””””doing it for love.”””””” I won’t do you the disservice of burying the lede: Big Daddy is 95 minutes of kidnapping apologia. Adam Sandler and all the one-note characters he played in the ’90s were just generally the worst and Big Daddy was no exception.

He’s an unfunny, misogynistic dirtbag (surrounded by flat female and minority characters) who we are supposed to become increasingly charmed by as he endeavors to parent a child — who, let’s not forget, he has taken for his own in an effort to woo a woman he supposedly loves but then later slut-shames for working at Hooters — by teaching him a quick way to pick up a misdemeanor for Public Urination. Suffice it to say, this movie failed the Bechdel harder than 12 Angry Men.

Fucked up.

3. The Santa Clause


The Santa Clause begins with Tim Allen murdering Santa, a tragedy that’s essentially glossed over by all involved, particularly the community of old-but-toddler elves who have been working alongside him for purported centuries. Over the course of the movie we’re meant to fall in love with petty Tim Allen as he learns how to succeed Santa (an “incredible” feat that involves gaining weight, growing a beard and going gray) (and let’s not forget his weird sexual tension with a 10-year-old-or-is-she-1,200-but-either-way-it’s-bad elf named Judy), but that’s merely the literal take.

A far more reasonable interpretation says that, actually, Tim Allen is a lost soul who’s taken to a basement (where he gains weight, grows a beard and goes gray) to live out the rest of his days under the PCP-induced delusion that he’s Santa as a way to cope with the depressing realization that his marriage failed, he kind of sucks and he’s fallen out of favor with his son, thus enabling him to justify the fact that he only sees his child on Christmas.

Fucked up.

4. The Parent Trap (the 1998 version)


The entire premise of The Parent Trap is unacceptable. Two parents who are filthy rich, well-educated and ostensibly not institutionalized-levels of unfit to make decisions get divorced and think it reasonable to separate their twin daughters and lie to them for the rest of their lives about each others’ existence?! Off the bat this is ludicrous. In the world I live in, Lindsey Lohan-as-twins would have to be sent home from camp immediately upon uncovering this truth and spend the rest of the movie in therapy.

Instead, they embark on a quirky adventure to convince their lovely mom and shithead dad — who is engaged to an actual sociopath because, I dunno, she’s sexy — to get back together. At no point in the unraveling of their dad’s engagement are we meant to conclude that he’s a piece of shit unworthy of their mother’s time. By the end of the movie he’s absolved of all responsibility and the plan works and everyone cheers.

Fucked up.

5. Home Alone


Home Alone has a somewhat shaky premise: a mother forgetting one of her children exists for four hours while an eight-year-old masterminds the torture of two robbers, but frankly I’ve seen worse (Adam Sandler as a lovable kidnapper). What’s really outrageous about Home Alone is how it parades itself — through a score of jaunty tubas and quick cuts to a precocious child mugging for the camera — as a super fun movie that’s not at all a stomach-turning display of utter violence and gore. Five words: A. Nail. Through. The. Foot. How are we supposed to laugh and not conclude this kid is 100% a future serial killer? I might balk at the epic suspension of disbelief required to enjoy this movie if I didn’t think that its biggest fans probably pulled wings off of flies in grade school for fun.

Home Alone: Horrifying sadism for the whole family!

Fucked up.

Photos via Getty Images.

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  • Harling Ross

    this post caused me to laugh out loud a total of six times in a quiet office, i will have you know.

  • Robin

    “this movie failed the Bechdel harder than 12 Angry Men” made me laugh, then feel very intellectual for getting the joke

  • BRILLIANT. STUPENDOUS! HILARIOUS! You slayed them all, Haley! If I ever have to do a trial by word combat I hope you will fight for me; you will obviously reign supreme. (I’ve been watching too much Game of Thrones lately, can you tell?)

    • Haley Nahman

      Never too much!

  • RaquelT18

    FINALLY!!! I have been saying for YEARS that the Parent Trap is honestly one of the most fucked up movies ever. I can’t even watch it anymore. Who lies about their kids’ parents being dead?? And then all of the sudden they are the protagonists?

    I knew I was finally a full grown cynical adult when I started feeling bad for Meredith. She’s not that nice, but come on– the girl is just trying to live her life and then she is completely misled by Dennis Quaid. Not cool.

  • I loved The Parent Trap. Only after I read this post did I realise how messed up it was, LOL.

    Charmaine Ng
    Architecture & Lifestyle Blog

  • Julissa

    You will never see Mrs. Doubtfire the same after watching this https://www.youtube.com/watch?v=1Ckv_Dz-Sio

    • Haley Nahman

      Omg I’m dying

    • Jamie

      This is too funny!

      • Grace B

        there’s one for Ferris Bueller’s Day Off too…it’s amazing.

  • Yvonne Dunlevie

    You have to admit though — Dennis Quad’s GF in Parent Trap is pretty sexy

  • John

    Chill out

    • Haley Nahman


  • Imaiya Ravichandran

    i died and came back to life after reading the santa clause description…(in a v good way).

  • Mind = blown. I will never see these movies in the same way again, but it’s ok because you’re completely right.

  • Ooh the Mrs. Doubtfire and Big Daddy breakdowns make me especially annoyed to be alive during such antiquated ideals (also makes me annoyed that I was alive for: “that’s so gay” was a perfectly acceptable insult, Monica Lewinsky’s life was totally destroyed, so was Anita Hill’s, and Marcia Clark, Vanessa Hudgens having to apologize for her underage nude leaked photos. AND IT WAS ALL TOTALLY NORMAL

    Also this interview where Diane Swayer basically shames a 20 year old Britney for breaking up with Justin, having a big butt, and masturbating UGH 90s/early aughts!


    • Lebanese Blonde

      Oh my god Diane Sawyer and the excessive slut shaming.

    • Katrina Elizabeth

      Ugh this is terrible

      • Stephanie

        It’s really troubling. She interrogated her the whole time and I actually thought Britney was very poised.

  • Nat Ch

    YES!!! I didn’t enjoy Home Alone. Ever. None of the times I tried to watch it. I felt sorry for the thieves, I wanted something to go wrong to the kid.

  • Sabletoothtigre

    But like, what if there was a Home Alone remake in which the kid actually DOES sadistically torture the home intruders, like Saw-style or something? Too much? Idk, just me? Kind of like the OG Evil Dead vs Evil Dead remake?

    • Haley Nahman

      lolll that’s too 2016!

  • lateshift

    This list is gold. 100% agree! Just have to point out that the Parent Trap of course isn’t really a 90s movie, which may explain the fkd-upness. (Yes, I’m THAT person. Sorry.) Yeah, THIS version was made in the 90s… but the ridonkulous premise was birthed in the ’60s, when the details around the edges actually made it a little bit worse, tbh (a major plot point hinges on physical abuse of a child by a non-relative! Mom’s path to happiness lies in radically changing herself to conform to just about every gender-related expectation…as in: dress sexy, cook a huge time-intensive meal without being asked, be the super-smiley and undemanding option while dad chooses between two women, etc etc.)! But anyway, the point is that the whole fkd up flick was just airlifted lock, stock and barrel from the 1961 version.

    • Haley Nahman

      Fair!! I’m more poking fun at the fact that so many of us didn’t realize this was fucked up initially, as the case with all of these. I loved it! So tbh I’m just shaming my former self.
      Unrelated: I think my parents named me after Haley Mills!!

  • Peter

    Even when I was little I was perplexed by how these lovely, simple fathers were always so easily conned. I mean, Billboard Dad? More like Clueless Dad.

  • MMR

    Wow, on point

  • pamb

    I couldn’t wait to show my tween daughter Sixteen Candles, my favorite of the John Hughes movies (Ferris Bueller: as a Chicagoan, I knew it was impossible to do the things they did in the order they did them and still make it home in time. Breakfast Club: too talky, too angsty).

    I had remembered the offensive Long Duc Dong stuff, had forgotten the gifting of his drunk girlfriend that the ‘hero’ gives Anthony Michael Hall. They wake up in the car and can’t remember if they had sex! So funny! She doesn’t seem mad that her boyfriend would do that to her! And we’re supposed to cheer that Molly Ringwald wins up with him!

    What a bummer.

  • Herd Nicholas

    really enjoy your articles

  • Gene

    Has anyone revisited The Mask or any of the Ace Ventura movies lately? Super effed,and yet… “bumblebee tuna” is used at least on a weekly basis by me.

  • Gina Fuchs

    + Cruel Intentions (but that one might just be too obvious)

  • Ciccollina

    So enjoyable <3

  • Egg

    Mrs. Doubtfire is an example of someone in drag, not idenifying as a woman. Even Rupaul loves Mrs. Doubtfire!!

  • Lindsay

    I’ve realized as I’ve gotten older that most if not all TV sitcoms and kids movies are based on one really big lie. If one person told the truth in any of these circumstances, problem solved. yesh.