Dust off your fave '90s dramedies and save them to share with your angsty love-struck teen

I was barely one when Pretty in Pink came out, but who cares?! I totally understood what Andie was going through.
When I was a teenager I happened to discover Molly Ringwald and her triad of John Hughes goodness: Sixteen Candles, The Breakfast Club, and Pretty in Pink. Even though I came of age in the late 1990s and early 2000s, I was drawn to these 1980s films with a fervor that I can't quite describe. I didn't just like them: I loved them. In fact, until I was introduced to Penny Lane in Almost Famous, I felt like I was Andie Walsh and Andie Walsh was me (except, of course, I would have totally picked Duckie).

I remember my mother walking by while I was in one of those fantastic spells in which you watch seven or eight hours of movies just because it helps life make sense (you guys did that, right?). Sometimes she'd stop and watch, and other times she'd make some kind of offhand remark. Since many a teen experiences some pretty tumultuous emotions, it might serve your relationship well to sit down and engage in some of these movies with your kid — if she or he will have you.

Even though I spent a good bit of my time pretending I lived in the '80s and listened to punk music, I spent most of my reality living in the '90s and listening to singer-songwriters and what would grow to become known as modern-day folk rock. When I met my best friend at fifteen, she introduced me to a couple of movies from our era that would prove to be just as good, if not better, than my Ringwald delights. These movies were the BEST when it came to making me feel like the characters just totally got me and that each movie just had to be about me and my situation, and ISN'T IT JUST SO HARD TO BE (your situation) AND IN YOUR TEENS. Because… isn't it?!

Here are a few that you might want to watch and share with your teenaged offspring. The films could be great starting-off points for discussions about sex, drugs, love, and everything else you want to know about your teen's life without being shady and snooping.

For the "Oh shit, I'm going to graduate school soon and I have no clue what I'll do with my LIFE" crowd

It may be about a group of recent college graduates, but many an almost-eighteen-year-old can relate to the gem that is Reality Bites. It stars Winona Ryder and Ethan Hawke as Lelaina, a would-be videographer, and Troy, a often jobless musician, respectively. These two spend most of their time pretending they aren't actually in love with each other, even though it's painfully obvious that they are. I mean, Janeane Garofalo and Steve Zahn are amazing as their friends (Vickie and Sammy), but when you're sixteen and so sure you're in love and it sucks, nothing beats Troy and Lelaina. Lelaina is spending her time shooting a mockumentary about the foursome and their post-collegiate struggles. Troy's not working, Vickie manages at The Gap, and Sammy's figuring out how he defines his sexuality. There's a lot going on here that could be appealing to your kid, and plenty worth talking about.

Talking about drugs and sex

The film Kids is definitely more drama than comedy — it was initially slapped with a NC-17 rating, and this was in 1995. Let's just say: it gets raw.

Kids, which was written by an eighteen-year-old, follows a group of sexually-active, drug-abusing, teenaged friends. At the time, many argued that the graphic depictions of violence, drug use and dealing, date rape, AIDS and sex aren't realistic, but for a lot of people, they are. The cast is made up entirely of then-unknown (Rosario Dawson and Chloë Sevigny) actual teenagers — instead of someone in their early twenties playing a teen. This makes the movie even better — everything feels real. The actions of the characters in the movie are basically the stuff of many a parent's worst nightmare, but the movie could also serve as a seriously valuable education tool if shown in the right way.

The movie to pull out when love sucks

Ok, I can't believe I'm going to go here today, because this movie is just HUGE in my world, but you guys: if your teen is nursing a seriously broken heart, get Before Sunrise by any means necessary (it's on Netflix if you're a customer!). Curl up on the couch, get under a blanket, pop some popcorn, and do what you need to do, because this won't be a film you turn off midway through to finish tomorrow.

Ethan Hawke (what? Again? Yep. My friend had a thing for him) plays Jesse, a young American traveling in Europe when he meets Julie Delphy's French character Celine. The two hesitatingly get to know each other on a train, and end up spending one night walking the streets together in Vienna. Just so you know: that's the whole movie — these two talking and walking, walking and talking, stopping to do a few other things, and walking and talking some more. It's 105 minutes of some of the most perfect cinema I've ever seen, and the 2004 follow-up (aptly titled Before Sunset) is just as good.

Alright: I know a whole lotta you guys are in your mid-20s to mid-30s: let's get it going. What's your favorite '90s dramedy you can't wait to share with your teen-aged offspring? If you've already got teens: do you bond through films, or another kind of media?

  1. I am a huge fan of Can't Hardly Wait. Call it a guilty pleasure… But Lauren Ambrose and Seth Green breaking down each others bullshit while locked in a bathroom does it for me everytime. (and come to think of it, in that movie she's totally the Molly R of the 90's!)

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    • Holy crap, I came into this thread pretty much just to mention the awesomeness that is Can't Hardly Wait. It's one of my favorite movies of all time.

      And Lauren Ambrose is SO the Molly Ringwald of the 90s.

    • You have completely read my mind and posted my thoughts. I thought I was the only one loving THAT part of that movie the most of all and thinking the same about Lauren/Molly R. Thanks for validating my opinion AND the movie.

      • Haha, thanks! It personifies the 90's dramedy to me. So quotable. So cutely unrealistic. Full of sexy people who touch their hair too much. I still text my friends saying, "Happy Rex Manning Day!"

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        • THIS.
          My girlfriends and I used to pull out and watch Empire Records all. the. Time!!!!

          "Oh Rexy…you're so sexy."
          "I don't feel the need to explain my art to you."
          "Rap. Metal. Rap. Metal. Whintey Houston?!?"

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          • Lucas, what's with you today? Yesterday you were normal, and now you're like the Chinese guy from the Karate Kid.

            What's with today, today?

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    • Considering that I am designing a tattoo based on the movie, I would say YES I AM A HUGE FAN OF THIS MOVIE! (Yes, I am putting it in all caps). For my birthday last year, the only thing I wanted was to travel to the store where the movie was filmed. I live in NC so it was only a 3.5 hour drive and I did go! I didn't want to leave! My boyfriend gave me the movie poster as an xmas gift. Seriously best movie ever ever ever.

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    • YES YES YES. My brother and sisters and I watched this movie OVER AND OVER. When I met my husband he had NEVER seen it, which baffled me — it's a VERY Sean movie. I went to work one day and told him to watch it while I was gone. When I came home, he was like "I just watched it six times in a row. I love this movie." To this date, it's his favorite film.

  2. If you haven't seen it, check out Flirting. It's an Australian film with Thandie Newton and a young Nicole Kidman before she transitioned to Hollywood…although Kidman is in a supporting role. This movie always reminds me of my first real love at 16 years old. Sigh…

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    • I was OBSESSED with that movie when I was 15, and I decided that I was going to name my daughter Thandie (I didn't, although I considered it). So good!

  3. When a Man Loves a Woman…and really all the Molly movies from the 80's. Something about them spoke to me. I'm struggling to think of movies of the 90's that were "so my life"…and I was totally a teenager of the 90s'….and i cant think of any….

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    • Many many yeses to 10 Things I Hate About You and Cruel Intentions! And American Beauty absolutely, not so much a dramedy, but still completely amazing, so who cares? It's life affirming, I tell you!

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      • This night I woke up and thought "I forgot Romeo and Juliet"!!! I saw that five times at the cinema and bought the video without owning a player. You know, just to have it… 😉

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      • Romeo and Juliet times ten. I still have that soundtrack, and I still adore it.

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    • 10 Things I Hate About You made me want to be Julia Stiles.

      Cruel Intentions *swoon*

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    • as a teen, i really didn't have the patience for sappy love movies…but i totally fell in love with 10 things i hate about you.

      i suppose it just shows how much of a shakespeare nerd i am. pretty much my favorite sappy love movie of all time is the kenneth branagh much ado about nothing.

      but, as for cinematic bonding with my parents, that totally happened through me and my dad watching cheesy action movies like die hard. i'll probably be that kind of parent myself.

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      • I liked the way that the cliques in that movie were so exaggerated that they seemed silly and that the people you really fell in love with in the movie were the ones who didn't really belong to any of the cliques.

        Also, it was filmed in the area I grew up in so a lot of people I know went to be extras, so I guess it holds a special place in my heart. 😉

  4. I will be re-watching "My So Called Life" when my daughter enters her pre-teens. It will help to remind me how it feels to be so angsty and full or hormones.

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  5. 'One Perfect Day' is an indie Aussie film from the 90s. Love, drugs and raves.

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  6. My good friend was figuring out all sorts of sexuality stuff, so we saw every indie-gay-move that came out in the late 90s-early aughts(sp?) My hypothetical kid's immediate family is going to be quite hetero, so I'm excited about showing them "But I'm a Cheerleader" and Hedwig. You know, once Hedwig will be interesting instead of terrifying (what with all the bits being chopped off).

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    • Wasn't "Better than Chocolate" also out around the same time? I LOVE "Better than Chocolate"!!!

    • Good call on "But I'm A Cheerleader" – it was a watershed movie for me as a queer youth. That and "The Incredibly True Adventure of Two Girls In Love." (Which I haven't seen since I was a teen and should probably get my hands on again!)

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      • yes, yes to all of these! "…two girls in love" is such a cute movie that so few people have heard of. i was introduced to it (along with buffy) by my dyke-mentor before i was gay. an integral part of the conversion, i'm sure 😉

  7. I look forward to sharing my '90 angsty teen love/life faves with my babylings on day. For me, it would be My So-Called Life (the only show that got lusting so hard for someone that you love the way they lean!) and Freaks and Geeks (<– because who didn't feel like Lindsay Weir some times).
    Movie wise, But I'm A Cheerleader was huge for me – the wanting, the confusion, Clea Duvall = ah-mah-zing! All Over Me was another huge, life-changing movie. All the questioning and awkwardness and clumsy first-time love as a queer teen was beautiful and heart-wrenching and just… it. And Leisha Hailey is still my hero!
    These movies/shows got me through first kisses, broken hearts, coming out and the general mind-fuck that is being a teenage girl. I hope they are as kind to my children as they were for me…

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    • Yessssss! That is amazing. Have you guys seen the follow-up? God, I love those movies.

      • Before Sunset was the movie that Ben and I watched the night I finally told him that I wanted to be with him and then seconds later told him that I loved him and, "I love you too" came gushing out of his mouth.

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  8. I watched Moulin Rouge every. single. day. in 7th grade. It seemed to fit every mood I had and it's a musical, so ++good.

    Also, I recently watched The Breakfast Club and realized what a TERRIBLE, AWFUL movie it is.. but as a teen, <33!

  9. As far as 80's movies, it was Say Anything for me… oh, Lloyd Dobler. And then in the 90's, Better than Chocolate was the first queer movie I had ever watched and it helped make certain feelings I was having make SO much sense! And, not going to lie, Clueless was one of my favorite movies as a pre-teen. Living on the outskirts of LA, I thought that was what my life in high school would be like and oh man, was I wrong!! haha OH MY, and The Craft!! Okay… I need to stop now.

    • I can't even TALK about Say Anything without getting 18 shades of emotional. I shot a wedding this weekend and the couple had their first dance to "In Your Eyes" and I thought I was going to pass out.

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    • Lloyd Dobler!! He was like what every boyfriend should have been to me. SO many good lines in that film…"Don't be a guy, Lloyd. Be a MAN." The whole movie…SO good.

    • Oh man, Clueless. YES.

      And it's from the Oughts, but along the same lines: Mean Girls.

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      • Haha, Clueless! Mean Girls definitely fits in there, and to me so does Easy A. The rumors in high school can be brutal. I was a pretty big fan of Practical Magic, too.

        On the TV end of things, Freaks & Geeks, My so-called Life, and now Parenthood on nbc.

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  10. A slightly obscure gay teen rom com is Beautiful Thing, which I became briefly obsessed with as a teenager. I think it was the first film I saw portraying working class gay people.

  11. I feel like I could have written this…. I was born in '87, but I was OBSESSED with 80's movies throughout my middle school/high school years.

  12. I loved watching Daria in the 90's! I have seen all the movies mentioned except for a few and I am sooooo making a movie weekend out of this blog!

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  13. I was never into chick flicks or teen movies. But I'm having a blast showing my 10 year old, extremely girly, High School Musical-watching niece my fav action flicks from my childhood. We've we're working our way through the Star Wars and Indiana Jones trilogies right now.

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  14. It's not really an angsty teen thing, I guess, but when I was thirteen, I attended a birthday party where we lined up to get tickets to see Titanic, and because it was sold out, we sat on the floor for all three hours of it.

    Then again, it was kind of a teen movie, since Rose was seventeen in that movie. (Which Kate Winslet did NOT look.)

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    • Ohhhh man. If we're going there, I need to confess that I saw Titanic twenty-seven times in theaters. TWENTY-SEVEN. I was one of those girls.

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  15. Agree with all of the above… a movie I wish I had seen as a teenager was Water Lilies, which is a French movie about three teenage girls "coming of age" as they say… loved all the Molly Ringwald movies and had a huge crush on her. Including the oft neglected For Keeps. I was also obsessed with the Drew Barrymore flicks Ever After and Never Been Kissed. We'd always watch Practical Magic at sleepovers even though its not particularly angsty.

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  16. Yes! to Moulin Rouge (knew every word to every song!), Never Been Kissed, Empire Records, SLC Punk, Daria, and Girl Interrupted. Gah, this is making me so nostalgic and emotional, my little girl is due to arrive in 2 months, and I know she will love these in about 15 years 🙂

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  17. not gonna lie, any time Go is on TV, my entire life stops 🙂 don't know what it would teach my kids (other than studying tantric sex could lead to house fires), but sooooooo love that movie!!!!

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  18. SINGLES

    and also a vote for The Labyrinth (although technically I think this one came out in the late '80s) but best movie ever, nonetheless.

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    • I totally love Singles, though I only watched it for the first time less than a year ago. I have since watched it 3 times. LOVE LOVE LOVE!! That dating video is the stuff of legend.

  19. I so wish I had seen Kids under better circumstances. My mother had found out that I lost my virginity (I told her) and she flipped. After forcing me to tell my father (and hero), she made me watch Kids with her. Yes, some teenagers may be able to relate to this, but for a girl who lived out in the woods in Northern Canada, was in a monogamous relationship and never dabbled in drugs, this couldn't have been further from my reality. It does, however, make me really happy to know that some people liked this movie and that it's got a good place in their lives. I will never ever show it to my child though. Everything else on this list will be on the shelf for the little ones when they're not so little anymore.

  20. Before Sunrise is one of my fave movies ever, and definitely my fave love story movie.

    However, I HAVE to mention Love Story (http://www.imdb.com/title/tt0066011/)… I think it would appeal to the Offbeat Bride in a lot of us (they don't get married in a church, which to her Italian Catholic father was pretty crazy lol). It is also the movie where the famous quote, "Love means never having to say you're sorry" came from.

    • P.S. It wasn't 90s or even 80s (came out in 1970) but it still had to be mentioned!

    • Aww, Love Story!! The same friend who introduced me to Before Sunrise & Sunset also introduced me to that, and Love Story is one of my all-time favorites.

  21. Although it is a late 90's flick, i'd like to throw 'she's all that' on the list. One of mine and my my hubs fave movies ever!

  22. Dazed and confused was a big one for me and my friends as teenagers. Even though it's set in the 70s, it could have been our lives: driving around with friends, looking for something to do, ending up in the woods at a party, trying to get awesome concert tickets etc etc.
    Mallrats, Clerks and Chasing Amy were also big ones. And for some weird reason, me and my boyfriend LOVED So I Married an Axe Murderer. Must have watched it together 20+ times.

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  23. I love so many of the films that have been mentioned here, 10 things I hate about you, Romeo and Juliet, Girl Interrupted… I have to say I have a potentially sad and pathetic love affair with Clueless haha.
    But I bonded with my dad as a kid whilst watching Star Wars (the classics) and I STILL love it to this day…with a collection of over 200 DVD's, I know they are going to be important in bringing up my children when we have them (after our wedding next year!).

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  24. Absolutely Empire Records! And did anyone mention Mad Love yet? Also, as a preteen, I was obsessed with Camp Nowhere.

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  25. Yes ALL OVER ME!! Love that movie! Also, Satisfaction amazing 80's movie. Full of sex drugs and rock n roll!

  26. Oh man — Reality Bites, Before Sunrise, the Breakfast Club, Freaks and Geeks. I can't wait to watch these with my children. These movies can spark some great conversations.

    Also loved 10 Things I Hate About You; my brother and I watched it over and over one summer. We still refer to it as "The Summer of 10 Things".

    • my sister and I refer to movies like that as well! We had a summer of "Clueless" and "Now and Then" (which made me want to ride my bike and solve mysteries with my best friends), and another of "Ever After" with Drew Barrymore. I also spent most of the 8th grade obsessed with "Romeo+Juliet". A "worldly" middle school friend told me that "Clueless" was based on "Emma", and that also started a huge Jane Austen movie obsession. The stories made so much sense to me in high school, and there was the added plus of awesome historical costuming. OH, I should add that "Sense and Sensiblity" was also a summer movie. Even my dad was into that one…

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  27. I have been planning on using Kids as a learning tool for my future children when they come of age about the dangers of unprotected sex; I will also be employing Requiem for a Dream to show them the dangers of drugs. hell I may even throw in SLC Punk, poor poor Heroin Bob. D:

    This article was awesome..

    and I'd just like to throw it out there:
    Labyrinth is also my favorite movie everrr! <3

  28. Ever since I saw the raw and realistic movie, Kids, I was planning to use it for my future kids as a lesson in using protection when they are old enough to understand. I would like to use Requiem for a Dream to warn them about drugs; another all too realistic movie that is about drugs and what people will do to get them.

    that being said, I'd like to say: Labyrinth forever!!! <3

  29. I know it's a 2004 movie, but Wicker Park! I was totally in love with Josh Hartnett 🙂

  30. This is great. My husband has been collecting childrens cartoon series for our child. It actually started before we were even pregnant. Does anyone remember The Racoons or The Smogies? Kids cartoons just seem so warped these days and we decided we would rather expose her to our favourites like Fragglerock over… I am so out of the loop I can't even name a current kids cartoon. Josie is only 4 months old but I think I will start a collection for her teenage years and it will definitly contain degrassy high. Thank you Stephanie for getting me to look ahead to the future. It may be hard to uncover some of these oldies in 15 years from now.

  31. I have too many to list, but Heathers is at the top. I had such a thing for Christian Slater that True Romance, <Untamed Heart, Bed of Roses, and The Legend of Billie Jean are also on my list. (I am actually blushing thinking about how many times I saw Untamed Heart in the theater at 14.) The early 90s were good to Slater.

    I really loved some movies as a teen, like Reality Bites (soundtrack still on rotation) and Teen Witch (first time I really paid attention to French kissing and was scandalized!) I was OBSESSED with For the Boys and nearly burnt out the VHS tape (but passed it on to my niece a few years back). I was already out of HS when Drew Barrymore became my girl-crush with Ever After, Never Been Kissed, and I discovered Boys on the Side.

    Movies I am still kind of obsessed and will watch if I catch them on TV: Newsies, Much Ado About Nothing, Interview With a Vampire, Empire Records, Clueless, The Crow, Defending Your Life, Now & Then, Willow, Say Anything, Cry Baby, Joe Versus the Volcano, Girl, Interrupted, Half Baked, Romeo + Juliet, Shakespeare in Love, Edward Scissorhands, Dazed & Confused, Chasing Amy, School Ties, Benny & Joon, and the most obsessed that I use it in teaching still Dead Poets Society.

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    • Newsies! yes!

      I also loved the Last Unicorn, because although it's not quite like most of the others listed here, I never really went through the normal teenage drama thing (it was more philosophical and religious to me), and this movie had some excellent ideas in it. It's relaly beautiful and well written (the book is good to!). Plus it's like the only kids movie ever that doesn't have a perfectly happy ending…

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