Films that Don’t Hold Up
Over the weekend I had a funny experience. I had been really excited to rewatch Serendipity (it came out in 2001 when I was twenty, and I’m not sure how long but it’s been since I last watched it… maybe ten years?). And WOW, It did not hold up for me.
It definitely had its good parts. Mostly, it made me nostalgic. New York was my home for fifteen years and I miss it a lot, especially during the holidays. Ice skating in Central Park, the hotel (and department store window) decorations, the hustle and bustle of the city this time of year… this is a good one for New York holiday nostalgia. There were some very funny moments too. But otherwise, I kind of hated it?
I have found over the past few years that a lot of the films I loved ten or twenty years ago don’t really hold up.
Often that is because of racism, fat-phobia, homophobia, a lack of diversity… I could go on. In the case of Serendipity, it wasn’t anything overtly problematic, moreso it was maddening and a little stressful to watch. Also: perpetuating and encouraging bad romantic behavior. I really hate the idea that you could be in a relationship (or engaged / literally about to walk down the aisle) while actively looking for something better. I found myself saying Poor Bridget (Moynihan, her character’s name is Hallie) over and over again. Here is John Cusack (Jonathan), about to marry her in a few days… running around New York City looking for that godd*mn book with Kate Beckinsale (Sarah)’s phone number in it. A stranger he met for just a few hours, years ago on some chance encounter. What an ass!
Maybe it’s just me but if you are that hung up on a stranger, you probably shouldn’t be engaged. Jonathan ultimately came to that conclusion on his own but man – I was furious, and really sad for his fiance. I felt less angry (but still uneasy) about Sarah’s situation – her boyfriend Lars (who is is played by John Corbett aka Aiden Shaw) was pretty self absorbed and kind of a jerk. But still, here she is – engaged and flying to New York to try to track down some stranger she met for a couple hours, years ago. This behavior shouldn’t be romanticized!
I love the idea of fate and soulmates and destiny etc… but this isn’t it!
It’s funny to me though. I remember watching it at age 20 thinking it was just the most romantic thing ever. At age 40 it made me angry. Angry in the same way I felt at Sex and the City for having Carrie and Big end up together. While I will always love SATC (the reboot comes out this week and I can’t wait!), I felt that it was an irresponsible choice on the writers’ behalf… encouraging leagues of women to hold out for the jerk they’re dating to change and finally realize they’ve actually been in love all this time. That just doesn’t happen (or rarely happens) in real life. Carrie and Big are the exception and not the rule!
I’m clearly a little fired up about this… What films don’t hold up for you? I’d love to chat about it in the comments section! A reader had messaged me saying she felt the same way about You’ve Got Mail. (To be honest I don’t remember what happened in that one, do I need to rewatch it?)
Even though it’s still a fun movie to watch, My Best Friend’s Wedding definitely doesn’t hold up nowadays! The pact the two friends made was if they were still single by the time they’re 30 (THIRTY!!!), they’ll get married. That alone is wild! Also Cameron Diaz’s character is still in college, engaged to a 30 year old, and is leaving school to support his career. Couldn’t she just finish college? Re-watching it last year was so wild!
I agree! I was just talking to someone about how terrible Julia’s character is in this movie! It’s so cringey to watch now.
100% agree with all of this!
Co-sign this sentiment. Also, the clothes in that movie hurt my eyes. I get that they are trying to juxtapose Julia Roberts’ city-gal style with Cameron’s girly-girl, but it’s all atrocious. Baggy gray pantsuits? Belly shirts? All of that Pink/Green/Yellow brunchwear with pearls? I can’t.
HAHAHAHA Agree!
I completely agree!!!!
Can we please talk about how creepy Sleepless in Seattle is? No one should fall in love with their stalker. Also Bill Pullman’s character (with no baggage and excellent taste) seemed like he was too good for a woman trying to long distance cheat on him because of a radio talk show.
My family didn’t have a high enough cable package to have Disney Channel when I was growing up, so it was always a treat to get to watch it at my grandma’s house or friends houses. I used to always luck out at my grandma’s and be over there when the Disney Channel original movie Stuck in the Suburbs was on. It was my FAVORITE!! (About two girls that accidently switch a cell phone with that of their favorite pop star, who happens to be filming music video in their town).
When Disney+ came out a couple years ago I was so excited to get to watch this movie for the first time as an adult. Oh my gosh – IT SUCKED!!! The plot was so insanely unrealistic to watch as an adult on so many levels. And the acting was terrible! I wish I had never re-watched it hahaha.
xoxo A
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I’ve never seen that!!!! Won’t be watching it, haha!
I watched Sleepless in Seattle with my 15 year old daughter who heckled the whole plot all the way through. Proud of that girl, ha!
Okay YES I feel exactly the same way about You’ve Got Mail. The Tom Hanks character comes across as creepy — like who would trick someone for that long? Love Sleepless in Seattle though.
You are totally right!!!
Yes! Rewatched You Got Mail for Valentine’s Day and was furious at the emotional cheating (on both sides) and manipulation by Tom Hanks. Also, Tom Hanks is kind of an asshole in the movie. Here for Greg Kinnear!
Oh my gosh, YES! So many romantic comedies and now Hallmark Christmas movies doing the same thing and it’s really not okay. True love is acting with integrity and not these narratives we keep seeing.
Yes, THIS!
I can’t think of any other one right now, but I watched Serendipity on Friday night! I felt the same exact way as did my husband. We used to love this movie, and we both love that it’s filmed in NYC. BUT, it was terrible and I found both of the characters to be so annoying. What DID hold up is how funny I think Lars (Aidan) is! His performance! His video!!!
The Devil Wears Prada is still fantastic but I couldn’t believe how unsupportive Andy’s boyfriend and friends were! There’s nothing wrong with grinding for a year knowing it will lead to your dream job, or dressing up and taking an interest in the fashion industry. Also her boyfriend was supposed to be a chef – how was he always home for dinner and every evening gathering?
I AGREE! We were talking about that a couple months ago!!!
Agree completely…I get so mad at him now when I watch this movie!
My husband and I say this every time we watch! Her friends are getting free bags, clothes, and still are being such jerks!!!
Yes!! I have always said this about Devil Wears Prada!
More of a general comment, but watching movies or TV shows and identifying MUCH more with the parents than the teenagers is wild. I rewatched The OC recently and the entire time i was wringing my hands…where are the parents?! Felt this way on Gossip Girl too on the rewatch.
Oh my god yes. Actually, watching Gossip Girl leaves me all sorts of conflicted. Why am I attracted to both the kids and the parents? Yuck!
My favorite, favorite childhood movie—-Little mermaid does NOT hold up for me. She saw a guy she thought was hot and gave up her voice to chase after him. Then he falls in love despite (because of?) the fact they have never had a REAL conversation. THEN she leaves her entire family behind to marry this dude? What a terrible message to send to young girls. Ditch your family, chase after hot dudes, and guys will like you even if you can’t talk?
Yes! Not to mention the fact that Ariel is SIXTEEN in the movie AND her Dad decides to turn her into human (permanently?) without even asking her if that’s what she wants!? Just waves his wand and knows what is best for her and she smiles in gratitude…
TRULY!!!!
Oh my god you are totally right!!!!!!
Lol. My mom was very chill but banned the Little Mermaid for that. Also said she was greedy and disobeyed her father. I laughed about it for years. Then when watching with my kids I realized she wasn’t as crazy as I thought.
You need to listen to Malcolm Gladwell’s podcast, Revisionist History – he reexamines the Disney movie and then gets a team to rewrite the script. It’s incredibly how the mermaids A) ostracize an older, single woman – I don’t think I’d be super happy with them either B) pit women against each other when it really is an issue with Ariel’s dad. Super interesting!
This was a tough one for me because it was my favorite, favorite movie as a little girl (the first thing I ever saw in theaters!) but the plot is so weird.
My niece got super obsessed w Little Mermaid last year when she was three but for some reason she truly thought Ursula was the main/best character so maybe that’s some weird sign of improvement? Hahaha
I could not agree more. I just had my first daughter In June and I literally lay awake at night thinking about this movie! It was my favorite as a young girl and now I struggle with everything. Ariel being so young, her dad having 7+ daughters and no mom so maybe 7+ moms, leaving your family for a guy, a guy who so stupid….. it’s all too much. Be better Disney
I feel the same way about Beauty & the Beast! I mean falling in love with your captor is actually the definition of Stockholm Syndrome…. barf.
OMG I just busted out laughing at this comment.. at work…. (I’m taking a 5 GD min break) LOL. Thanks for the chuckle Kiersten!
I watched the Santa Clause last year (and have regularly watched it at Christmas) and I was appalled at how fat phobic it was! The jokes definitely don’t hold up when viewed from a more modern lense.
Ugh that is so disappointing
I can’t rewatch Friends for that reason. The jokes are so disgusting. I can’t imagine being a teen girl watching that just thinking “wow my size means I’m ugly and awkward and everyone thinks I’m a pig.” The jokes were also so incredibly lazy and not funny at all. Hated it.
100% agree about Friends and the “Monica was fat” lazy joke! It’s also jarring to see how thin the actresses on the show were.
Yes. That joke was terrible.
Yes!!! Huge friends fan but it close to ruins it for me now 🙁
Also friends and satc low key homophobic at many points
Holiday Inn has a huge racist moment in it. Cannot watch. Holiday movies should leave you with the warm fuzzies and this ain’t it.
I have never seen that but I won’t watch it!!!!
I used to the that movie, but that scene ruins it!
My friends and I still watch it (as part of our Christmas movie marathon) but we skip right over February the second it comes on screen. That scene is just awful.
Grease. While I do still love a whole bunch of the musical numbers I saw it again a few years ago and was mostly bored.
I was just thinking about this last night while watching Love Actually for the first time since it came out back in 2003! Lots of icky “jokes” all rooted in fatphobia, sexual assault and harassment, and transphobia. I’m glad that we can see today how harmful these attempts at humor actually are, but it does make me think about what we find funny today that won’t be funny in two decades’ time (I personally think a lot of our self-harm humor will be viewed negatively).
Ugh I know, I picked up on those too!
I never understood the cult appeal of this movie even when it came out. Just for the creepy best friend trying to get with his friend’s wife. She makes it seem so sweet but in reality this would be horrifying and so uncomfortable.
You should check out Lindy West’s book, Shit Actually, where she talks about all of the problematic movies. Hilarious, but excellent points. The book came out of her essay about all the problems with Love Actually.
I watched Grease one evening the week of the Kavanaugh hearings when Ford testified. I had never seen the film and I ended up bawling uncontrollably afterwards. The movie is filled with casual mentions of sexual assault, women teasing men, and even gang rape. It’s awful.
WOW. It’s been years since I watched Grease but that’s terrible. And what a horrible context to watch them in.
Never Been Kissed! First of all, how did a 25 year old enroll in high school? Then, the fact that she flirts with her English teacher and he ends up attracted to her?!
HAHAHA YES!!!!
Oof, I recently watched What Women Want with Mel Gibson and that movie has aged horribly. I couldn’t even finish it because it made me cringe so much.
Oh my god YES. I did the same, during a Nancy Meyers binge in quarantine and felt exactly the same!
My husband loves the movie Major League. I don’t remember watching this 90’s movie in my youth, but it doesn’t hold up. One of the baseball players is pursuing his ex-girlfriend, now engaged to someone else. He literally FOLLOWS HER HOME (so he can know where she currently lives) and then also walks into her home – no knocking. The first time I saw it, the shock on my face. It was clearly made to be “romantic” and it just made me feel sad for our mothers/grandmothers that they may have thought at one time this was acceptable behavior (spoiler alert: she ends up with the stalker!)
Another baseball movie- bad news bears! Seriously bad news. Tried to watch with my kids and we turned it off within 15 minutes due to racism, language, and just offensive humor. Ugh!
Watched While You Were Sleeping the other day- I still loved it but my sister and I laughed the whole way through how it could be possible for us to love Sandra Bullocks character but in reality, she was really bamboozling this family!
We rewatched Casablanca during the quarantine. Not surprisingly, given the age of the film, I was kind of aghast at how unromantic it actually was. Lauren Bacall’s character is the absolute worst.
Lauren Bacall is not in Casablanca , it’d Ingrid Bergman
I recently rewatched Gilmore Girls and was shocked by all of the fat phobic and homophobic jokes! I can’t remember which carried through even to the reboot, but I did A LOT of cringing. It is always disappointing to pick up on that, particularly considering that the show featured fat actors and Michel was married to a man in the reboot (despite being “straight” in the original series!)
I’m re-watching it right now and was just telling a friend I couldn’t believe how I didn’t pick up on this the first time I watched it!
When I was rewatching Gilmore Girls before the reboot all I could think was “Emily is the only adult. Emily is right”. I borderline hated Lorelei and Rory watching in my 30s.
Sweet Home Alabama. Reese Witherspoon’s character is THE WORST. She’s super judgmental, outs her gay friend at a bar and is just overall a cantankerous jerk. Also I watched that movie thinking it was a young Matthew McConaughey and it is not. Very disappointing.
16 candles of course… it’s laughable how much we loved that movie (still do in a nostalgic kinda way). And anything with Eddie Murphy. Hahaha. Watched Trading Places with my teens and they did not find it amusing, even tho they grew up with parents that said “beef jerky time!” On the regular.
Not a movie and I’ll probably gain some enemies for saying this, haha..but Friends isn’t funny without the laugh track. SO many -phobic jokes (fat, homo, you name it!) that make me cringe so hard. Truly don’t think so many folks would find it funny if there was nobody laughing with them, haha!!
Completely agree. I stopped re-watching Friends because I want to preserve the nostalgia and really community of people that were so invested in that show and characters. But many, many jokes are not funny. Particularly Fat Monica especially “The One That Could Have Been” episode where Monica never loses weight and the plot line is because she didn’t lost the weight she eats all the time and is a virgin settling for a boring guy. Ridiculous. In the reunion, it would have been really powerful to have asked them about the jokes that don’t hold up and how they feel about them. Also, re-watching (especially compared to todays comedy) you realize how lazy the jokes are.
As person in her 40’s who is about the same age as the “Friends” were when it aired, I am so perplexed as to why teenagers and young adults LOVE Friends. I don’t get it at all. It is so ridiculously dated in every way – the fashion, the jokes (which were kind of cringey at the time TBH)., the ridiculous apartments. It was fine for its time, but it is just so lazy and cliched and again DATED. I don’t understand. I really do not understand.
It makes me sad to admit but you are SO RIGHT.
I still love You’ve Got Mail but Joe Fox was gaslighting Kathleen basically the entire time. Tom Hanks would never!
So, completely agree with the reader who wrote about You’ve Got Mail – love the New York moment, but Meg Ryan and Tom Hanks are in serious relationships (to the point where they’re living with their S.O. while having these emotional affairs – and I just feel more compassion for them them, especially Meg Ryan’s sweet/dedicated boyfriend). Also, other films that glorify toxic relationships? Something Borrowed (not exactly cinematic gold, but c’mon /Dax), Grease (the fact that Sandy had to change for Danny in order for him to like/accept her is terrifying) and The Devil Wears Prada (Andy’s boyfriend is the worst).
Sixteen Candles!! The Asian caricature is just SO. Bad. Also, they leave a drunk girl passed out with the “nerds” to basically do what they will. So cringey. Could not get through it.
I loved Reality Bites when it came out (the characters were a bit older than I was and seemed so cool). But then rewatching as and adult made me cringe – I was just like “get a job and stop whining!”
OMG yes! The scene where Winona Ryder’s character uses her dad’s gas card to get cash out of people induces parental rage in me now!
Same…this came out when I was in high school. We rewatched too and all we kept saying is “how is Ben Stiller the bad guy here?”
I appreciate this post very much. This has been on my mind a lot recently, too. 3 movies that I watched recently where I was struck by them not holding up-
1) Now and Then – besides smoking around a pregnant woman, the Christina Ricci/Rosie O’Donnell character left me feeling sad.
2) When Harry Met Sally – Meg Ryan’s character holds her own, but Harry’s mansplaining was not charming/funny and just annoying to me this time.
3) Heathers. This was always over the top but this time it was just unbearable. The violence is obviously problematic and it’s own conversation but the homophobia and lack of diversity in particular hit me hard and I could not finish it.
Breakfast at Tiffany’s is so egregiously racist that I’m still shocked at how it’s romanticized.
It’s Complicated! Love Meryl, but Alec Baldwin’s character is AWFUL. Controlling, gaslighting, stalking… not to mention sneaking around and cheating on his current wife. I rewatched it recently and almost turned it off, it was making me physically uncomfortable.
but that is his character—i dont think it doesnt hold up. I think it was kind of right on the money. He was bad news for her!
I actually agree. I generally think that movie holds up pretty well but yes, his character was AWFUL (but he wasn’t glorified or romanticized, he was just bad news and she found Steve Martin who was so sweet and lovely!).
Bring It On (a teen movie but and old fav)! Loved the dance routines but the tolerance of sexual assault, and the comments to LGBTQ characters just ruined it for me. High school, too, was full of that – back then we’d shrug it off or laugh! Now I cringe. So glad times are changing and we are speaking up against this more.
Ohh, I love this movie though I don’t put any weight on it but to enjoy. Seems like any movie from the past has weird, wrong things whether how the story is told or what the characters do or say. I always appreciate your views Grace!
I love this discussion so much! Thanks for raising the issue. Several times rewatching shows like Friends, The Office, Parks and Rec, West Wing, etc – all shows with cult followings that I used to love- I’ve felt uncomfortable with the frequency of jokes that are based on shaming or making fun of vulnerable populations. I’ve even brought it up in conversations with family/friends but have generally been told that it isn’t fair to use a critical lens from the present on shows or movies from the past. I disagree. It’s important to reexamine series that had a huge impact and influence on culture to recognize the harm they did. So many of the problematic shows and movies are still airing reruns on tv and available on streaming services, which means more people are continually being impacted by them.
I never watched The Office when it originally aired but watched it for the first time during quarantine last year. SO many of the jokes were awful!! It made me so uncomfortable to watch.
One of my favorite movies in my teens was the Fugitive with Harrison Ford and Tommy Lee Jones. I thought the tricks Harrison Fords character used to avoid getting caught were genius! I made my teenagers watch it after I talked it up for two days and they were not impressed. Nothing is problematic but all of his tricks are very low tech and have been done much better in later movies. It made me pretty sad that the magic was gone.
You know what movie holds up surprisingly well? Three men and a baby! It fails the bechdel test spectacularly, but there’s very little fatphobia, not much homophobia, and the jokes are still funny. I cant believe how much I enjoyed it – currently streaming on amazon prime
I know it’s total fantasy but Twilight was on the other day, it’s not even all that old but ugh. Cringe. I can’t believe young(er) me thought that was romance.
Not just movies! I DNF’d a book the other day because the heroine was engaged to someone she professed to love, but as soon as her childhood neighbor/crush who “disappeared” for a few years started sniffing around, the heroine was ready to ditch her perfectly lovely fiance, presumably at the first sign of romantic interest from the crush (…. not sure about this because I tossed the book in disgust).
Bridget Jones’s Diary – so fat phobic and problematic relationship behavior on SO many levels! I remember watching this as a teen and it seems like a different movie as a 31 year old.
Currently rewatching SATC and realizing how we’ve been constantly fed the narrative that toxic = passionate, and passionate = love. NO! Carrie and Aidan had a great, healthy relationship and the she did not give it a chance. It’s sad that a relationship like that is labeled safe and boring, instead of healthy.
Oh my god, the reader in question is SO RIGHT about You’ve Got Mail. Capitalist propaganda served with a side of cat fishing and emotional manipulation. Terrible movie!
I didn’t read all the way back, so not sure if someone already mentioned this one, but The Wedding Date. I have watched this movie probably 100 times and still love it, but it always pissed me off so much how Amy Adams character cheats with her sisters fiance, thus ending their engagement, never comes clean to her leaving her sister to wonder what went wrong all those years, until she gets caught for it, blames everyone else, and then still gets forgiven immediately by everyone and goes on to have a happy wedding. Deborah Messing’s character gets totally shafted in this movie!
I loved Blank Check growing up, and recently rewatched and was horrified at the end when the bank teller woman plants a romantic kiss on the kid! Yuck!
Mrs. Doubtfire didn’t age well at all. And The Parent Trap was one of my childhood favorites, but now I’m a mother to identical twin girls and we’re all horrified by it. The parents divorce and each takes a baby and agrees to NEVER SEE THE OTHER KID because joint custody is just too inconvenient. What?!?
Something Borrowed is all about sleeping with your best friend’s fiancé and eventually stealing him from her. Wow. So romantic, huh? I lived the book/movie when I first read/saw it,but just rewatched it a few weeks ago now that I’ve been married for 15 years and was horrified.
I know!!! I loved the book and the movie so much when they came out but feel exactly the same way!!!!
I have appreciated this thread SO much! And to echo everyone else here- OMG, YES!! Everything that was pointed out about Little Mermaid? My favorite childhood movie- ugh!!! And completely true- she is 16 and her dad is totally fine with her throwing away her life, family and identity for a dumb stranger who have never talked to her!!! I think I need to re-watch You’ve Got Mail & Love Actually – I remember having problems with at the time, but I brushed them off! And all the comments about Friends? – a 1000 times, YES!
I rewatched it recently too and I agree with everything you said. Also, with Miramax being the studio gave me a weird feeling of concern for the female actresses. It was a very strange rewatch. You’ve Got Mail has a ton of problems, I still love it as a love letter to NY but Tom Hanks’s character (Joe Fox) is not a nice guy!
I’m glad now that when the Rambo movies started rolling out in the early sixties I was just getting established and couldn’t really afford luxuries like movie theaters.Looking back, I enjoyed the first four Rocky movies Sylvester Stallone put out, but the Rambo character was ridiculous.I recently saw a snatch of a movie where the diminutive Stallone’s Rambo storms in on a tall rugged soldier who struggled to look scared (“I was just following orders!”)as he looked down on Rambo who had to stretch on his tippy toes to reach for the doomed soul.Of course Rambo was shirtless, sweaty and wearing a headband. I believe I saw another Rambo flick that opened a scene with a closeup of Rambo’s veiny forearm.Okay, Stallone was ripped but he was also small and ridiculous looking with scripts so bad there couldn’t possibly be any credible acting. I feel the same about the first Die Hard movie- for one, the “ultra-modern” hotel looks silly now, and the bad guys look act over the top like the Batman villains from the 1960’s tv show.
As time goes on your perspective changes, or it should, if you have been paying attention.
My favorite movies, Harvey, still holds up. I recommend it.