11 Tomboys and Weird Girls From 90/00s Movies I Loved as a Kid

I couldn’t take my eyes off the tomboys, weird girls, and smart girls in movies I watched as a kid. In the late 90s and early 00s, I was an awkward, shy, and nerdy girl so I naturally gravitated to girls in films that were… different, like me. These girls were brave, bold, bookish, outspoken, outcasts and seemed way cooler than I ever was. I wanted to be friends with them and create a secret club — and to be honest, it seems like as a queer grownup I’m now part of one.

Here’s a list of movie characters who I also think grew up to be part of this secret club — ahem, and by that I mean they’re probably gay now too. I only included movies and characters I specifically remember watching as a kid and not at other points in my life, so this list is subjective and I’m sure there are other tomboys and weird girls in films that totally changed your life too. Let me know who they are in the comments!


Matilda, Matilda (1996)

I read so much as a kid during the summer because there wasn’t much to do where I lived; we didn’t have cable, there weren’t other neighborhood kids around, I didn’t go to summer camp, and it was way too hot to go outside during the day, so I spent most of my days at the library or reading in my room on the floor. Similarly, Matilda consumed books like they were candy, except she was also a freaking genius. She resorted to books not out of boredom but as an escape from her abusive parents. Then she learned she could harness her anger into telekinetic powers! A smart, misunderstood girl with telekinetic powers? YES, PLEASE. I was hooked! Matilda was played by none other than Autostraddle pal and noted bisexual, Mara Wilson, who guessed that your first crush was Miss Honey. So in my book, Matilda grows up to be queer; that’s just the truth.

Jody, Gold Diggers: The Secret of Bear Mountain (1995)

I don’t care what anyone says, this is the gayest movie of all time. Please do yourself a favor and watch this movie on a summer night. Anna Chulmsky plays baby dyke Jody, a free-spirited teen with a bad reputation around town. Christina Ricci plays Beth, whose dad just died and who just moved to the area with her mom from LA. The two become friends and go on adventure to find the long lost gold of Molly Morgan, a miner who died on the mountain and let’s be real, a gay ancestor. Jody takes Beth on her boat and wears a captain’s hat: pure queer culture. The way these two fight to be with each other is just like the tears you cried for your first girlfriend.

Gloria, Richie Rich (1994)

Gloria was a tiny tomboy who only hung out with a bunch of boys. She’s a tough girl with a penchant for the Xtreme — rollercoasters, kidapults, riding ATVs, and taking down rich guys. She also likes baseball and just sort of tolerates Richie. In fact, by the end of the movie she says, “Richie, you’re alright!” Great assessment, Gloria! Boys are truly just alright. I’m pretty sure Gloria grew up to be a communist.

Ira, Friendship’s Field (1995)

My mom use to subscribe to Feature Family Films, which is an entertainment company dedicated to “wholesome” family films. They produced movies that didn’t have profanity, sex, or violence and taught “traditional” family values, whatever that means. They’re super popular with conservative Christians! I think we had a subscription because my mom caved and bought one from their savvy telemarketers and kept calling the house.

Anyways, the movies were actually really good and I loved watching them! There was one film in particular called Friendship’s Field that was about a 12-year-old tomboy named Ira who befriends a Mexican boy named Oscar one summer in 1965. Oscar’s family was hired by Ira’s dad to help pick the crops on the family farm. The white people in town are awful to the Mexican families and Ira and her family are confronted with the ugly truth that racism exists and they try their best to be white allies throughout the movie. I liked this movie a lot because it showed close enough depictions of what my parents experienced growing up as migrant farm workers. But besides that, I also was really drawn to Ira because she was unafraid to get dirty and beat up racist white boys who were picking on Oscar. Adult Ira is narrating the story and at the end you see she still works on her family’s farm and it’s implied that she got married to a man (which I never bought) and has children of her own and still rocks short hair.

Roberta, Now and Then (1995)

Now and Then follows the lives of four best friends during one transformative summer in 1970. One of them is tough girl Roberta who takes no shit from boys, especially when they say girls can’t play softball. She punches a boy in Now and Then and honestly it’s so punk rock. Roberta’s life is in flux at the moment, she’s grappling with the death of her mother and having feelings about her growing chest. Devon Sawa is her rival and love interest?? and one point they kiss and she wasn’t into it. Roberta grows up to be a supposedly straight Rosie O’Donnell and a doctor who delivers Chrissy’s baby girl. Honorable mention goes to Gaby Hoffmann, who plays Samantha in this movie — she’s definitely a weird girl who was into seances.

Amanda, It Takes Two (1995)

Ah, yes, It Takes Two was like The Parent Trap but with the Olsen Twins. Amanda is an orphan and Alyssa is a rich girl and the two bump into each other in the woods and decide to do a whole switcheroo to get the adults in their lives to fall in love with one another. I don’t remember how this movie explained how they were only lookalikes and not long-lost twins? Because I mean, come on! I’m pretty sure this is the movie that set in stone that Mary-Kate always plays the tomboy and Ashley plays the girly girl and they ran with it on a short-lived show called Two of a Kind. I remember buying a book at a Scholastic Book Fair about the Olsen twins and it said that Mary-Kate wasn’t really a tomboy and Ashley wasn’t really a girly girl and I was SHOOK. They sold us lies!

Becky “Ice Box” O’Shea, Little Giants (1994)

Becky “Ice Box” O’Shea is a legend. She’s a talented athlete and just wanted to play football. When her uncle doesn’t pick her for his pee wee football team because she’s a girl, she convinces her dad to start one so she could play. Becky is tough but also encourages her less coordinated, goofball teammates. The only surprising thing about Becky is her damn crush on Devon Sawa (to her credit, everyone had a crush on Devon Sawa back then) and how she gave up playing a super important football game to become a cheerleader to get his attention. I’m glad she came to her senses before it was too late and decided to get back in the game in a skirt! You go girl!

Kristy, The Baby-Sitters Club (1995)

My older sister was in love with all things The Baby-Sitters Club. I inherited her VHS collection of The Baby-Sitters Club 1990 TV series and watched them over and over again. To my delight, there was also a feature-length film! Kristy, our fave bossy tomboy, is too soft for my liking in this movie compared to the Kristy in the TV series. Although the story is about all of the babysitters and their friendship, a big portion of the main storyline is Kristy’s, which is pretty cool.

Eden, Blue Crush (2002)

Michelle Rodriguez can wear the heck out of some board shorts, amiright? might’ve been too young to watch Blue Crush at the time but I’m glad I didn’t miss out on badass hot girl surfers. The premise is pretty gay too — like three best friends living together and raising a kid sister and they competitively surf? Hmm, yeah! Eden was the friend who pushed Ann Marie to focus on competing instead of the guy who was courting her. My 6th grade best friend was obsessed with Michelle Rodriguez and this movie at the time and I’m pleased to inform you that she’s gay now.

Missy, Bring It On (2000)

The whole world stopped when Missy walked in for cheerleading try-outs and pulled out her wallet chain to do some back flips. Missy was an amazing gymnast and the Toros desperately needed her. She’s the one who pointed out that the Toros were appropriating cheer routines from the Clovers. Missy might’ve gone through a transformation throughout the movie and started being less “weird” but it was her I-don’t-give-af attitude and energy that makes her stand out from the rest. In addition, we all know that Missy and Torrance had A Thing.

Lilly, Princess Diaries (2001)

Heather Matarazzo is the ultimate weird girl. I didn’t watch Welcome to the Dollhouse until I was in college so I didn’t add Dawn Weiner to this list. But Lilly totally makes the cut because I owned Princess Diaries on VHS and watched it plenty of times. Before Heather Matarazzo was Stacy Merkin on The L Word, she was Mia Thermopolis’s best friend who had a cable show called “Shut Up and Listen.” She was an outsider like Mia and really into being anti-establishment at their high school — she really doesn’t care about what the popular kids think of her. Tbh, Lilly was annoying and obnoxious but she makes up for it by being a loyal friend. My favorite line is when she’s running up the hill to catch up to Mia and Michael and she’s like “Wait! Wait for me!” and two other people turn around and she was like “Not you, I don’t even know you!”


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Yvonne S. Marquez is a lesbian journalist and Autostraddle senior editor living in Dallas, TX. She writes about social justice, politics, activism and other things dear to her heart like Selena and tacos. She graduated from the University of Texas at Austin with a degree in journalism and has since written and edited lots of gay stuff for the internet. Yvonne calls the borderlands home, strongly identifies with her Scorpio moon sign, and really hopes to crush the patriarchy soon. Follow her on Instagram or Twitter.

Yvonne has written 191 articles for us.

88 Comments

  1. This list is amazing and I need to go back and watch Blue Crush asap.

    I have a weird relationship to that movie because for a while I used to say the Kate Bosworth/Anne Marie character was my root but in reality I think that was more of an “I want to be/look like her” thing because she isn’t really my type. Its kind of comforting to know there was a potentially queer Michelle Rodriguez character in the film and maybe that was giving me queer vibes about the movie in general even though I honestly didn’t even remember her being in it at all?? I’m excited to go back and rewatch it 16 years later!

  2. What a delight!

    I definitely identified with the weird girls real hard (Matilda!) and felt feelings about the tomboys, so this list is working for me in lots of ways. Personally, my favorite Lilly line from The Princess Diaries is “I just found out that my cable show only reaches 12 people!” (I would have sooo been one of those 12 people if I could’ve).

  3. 100% agree with this list, although my list would also have Kat from 10 Things I Hate About You.

    My mom was also pressured into the Feature Family Film deal, but I agree, I thought they were good movies (as a kid at least) and was just happy to have more things to watch.

    Wish I knew where to watch Gold Digger again, I don’t think I’ve seen that since the 90s but I remember really loving it (really, I was into anything that had Christina Ricci in it – Now and Then was definitely my favorite though).

  4. Wait, Michelle Rodriguez was in Blue Crush? I did not remember that. But yes, I’m sure she did rock those board shorts.

    And that scene in Bring it On – Missy and her backflips. Sigh.

    #OlderStraddler but not so old that I haven’t at least heard of most of these.

  5. #OlderStraddler GenX version

    Darlene – Roseanne
    Allison (Ally Sheedy) – Breakfast Club
    Watts (Mary Stuart Masterson) – Some Kind of Wonderful
    Tootie – Facts of Life
    Jo – Facts of Life
    Maryanne – Gilligan’s Island

    Take home message – there were better tomboy and weird girl options in the 90s.

    • Oh wow. Get out of my head… or my childhood memories or wherever. I’m prob somewhere between you and Yvonne age wise, but this list is nearly 100% representative of my pre-adolescent queer feels. I was obsessed with Allison, Watts, and Jo as a kid (Tootie was my bff in my head).

      I was just talking about Watts with someone like 3 days ago. I honestly can’t remember why, but I’m sure it will happen again because she’s the actual best (except maybe the part where she is pining away for Eric Stoltz when Lea Thompson is Right There).

    • Real talk someone once said, “Ugh you look like Darlene.” and I said, “Dude thanks!” there maybe have been thumbs up by me.
      All I’m sure is the person was confused why I thought that was a great thing.

      • I had a similar conversation about Anne of Green Gables. Guy I worked with saw the beginning of the PBS series and told me I reminded him of Anne and I was like “oh, I loooooved those books” and he was all like “there were books?” and “wow, you’re weird” and that’s when I realized he probably didn’t mean it as a compliment.

    • Bah bumped submit before I was done typing

      Anyway yeah you right the 90’s had better tomboy options in the 90’s. I think it was the influence of grunge, 3rd wave and how kickass the women’s teams were doing on the international stage.

      • The 90s had way better tomboys than the 80s, but the 80s were still better than the 70s.

        The only tomboyish character I can think of from my childhood is Kate Jackson on Charlie’s Angels.

        Oh, and Daisy Duke from the Dukes of Hazzard – which is late 70s and mostly early 80s. (Adult me is appalled, but 10 year old me was unaware of the racism and sexism and I just really loved that she drove as fast and as well as her (completely uninteresting) brothers and could rebuild a car engine in the dark and I was fascinated by how she looked in those tight jeans and high heels.)

  6. oh, man TWO OF A KIND (i think about that scene where the dad’s date sings karaoke to Rod Stewart’s “Da Ya Think I’m Sexy” at LEAST once a week)

    re: Babysitter’s Club- I saw Schuyler Fisk sing backup vox at a show in Charlottesville last year and she was pretty darn good! definitely improved the mediocre dude she was with hahah

  7. Wow, Gold Diggers The Secret of Bear Mountain that’s a movie name I haven’t heard in years. Is there a reason only 3 of the movies on this list get semi-regular play(at least twice a year)?

  8. Oh man, I was obsessed with so many of these movies as a kid and teen. I guess the three I continually played in rotation were It Takes Two, Bring It On and Now and Then. As a kid (well a teen too) I was a big Mary-Kate and Ashley fan, Mary-Kate was always my favorite. She literally played tomboys in everything, I guess I have a softspot for tomboys! 😀

  9. I want to add that I only saw The Secret of Bear Mountain for the first time like 10-15 years ago (in college), but if you haven’t seen it since you were a kid, I just want you to know that you weren’t reading anything extra into it, it is actually, truly, literally suuuuuuper gay.

  10. Almost this entire list is my childhood! Thank you for making me so nostalgic! I HAVE to watch all of these now, esp It Takes Two which I totally forgot about?? Such a good classic MKA film! Also totally believed and bought into their personas. I always was an “Ashley” but I feel like lots of queers I know are “Mary Kate”. The two genders!

  11. Ok some of these I’m like YES but others I’ve never heard of the movies

    But also like…Bend It Like Beckham and Stick It need to be mentioned!!! (Like MAN Stick It deserves to be mentioned SO MUCH bc uhhhhhh yeah young me was crushing HARD on the main character Haley and mayyyyybe being really into the scene where she takes an ice bath bc of all the muscles hurt bc gymnastics is hard should have been enough of a gigantic flashing sign pointing out that I wasn’t straight buuuuut it was not, somehow.)

    I also think Eowyn deserves an honorable mention bc…GIRL. “I am no man.” Fucking ICONIC. Also iconic: her armor. As a kid I was SUPER INVESTED in Faramir/Eowyn bc they were my two faves but as an adult I’m like…….marriage of convenience much???? bc uhhhh both can be REALLY read as queer-coded and idk if that’s intentional or not. (But also I’m still kiiiiiiinda invested in them as a couple bc uh both are so perfectly my type they’re probably the archetype for my type: studious nerdy dude who is not Manly Enough for some people who are assholes* and woman who is sick of sexist shit and looks amazing in armor/other sporty attire and could almost certainly beat me up.)

    *seriously fuck Denethor. I can only think of one fictional character I hate more than Denethor and even that is a close call.

  12. I believe Roberta was originally supposed to be gay and it was changed – I think I read that on this very website actually?

    Lilly for sure, I was so mad when they sort of smushed her together with a boy in the end, and so vindicated when Heather M turned out to be queer (which isn’t the same as her character but still).

    Secret of Bear Mountain I only saw the second half of, I came in when my little sister and her best friend were watching in high school and at the end her (straight) friend joked,”and now they kiss” and I was like “seriously.” It was not subtle. How is Christina Ricci not queer? I’d add Wednesday Adams to this list to make that three Christina Ricci characters pinging queer.

  13. I saw Gold Diggers in the late 90’s at a “Daughters On Campus” event in Tucson when I was probably 10 or younger. I had a huge crush on Christina Ricci (we had a VHS of Now and Then that I would watch like every weekend) so that was an upside to watching the free movie.

    I saw undertones of myself in the film as I saw their close friendship as something that was more than just friends. (I had some strange emotionally intense friendships with girls when I was in elementary school)

    Also you don’t get any weirder than Lydia in Beetlejuice, we would rent the VHS pretty frequently from the local 1950’s styled video store “The Pink Motel”.

  14. double shout-out to Lex and Dr. Ellie Sattler from Jurassic Park! In media and in real life, female masculinity is seen as problematic or suspect if it persists past puberty — girls are supposed to “grow out of it” — and one of my favorite things about that movie is the way it sets up a nice parallel between Lex, the prepubescent tomboy, and Dr. Sattler, an adult woman who didn’t grow out of her tomboyishness and isn’t denigrated, devalued, infantilized, desexed, or killed off in the first fifteen minutes for it. She’s the protagonist! A grubby gal who digs in literal animal shit gets to be at the forefront of the movie, and she’s not made to assimilate into proper femininity as a condition of her surviving to the end credits. I love it. I love Dr. Sattler so much. I had the biggest crush on her when I was like ten and you know what? I still do. And setting her up like that in parallel to Lex is so important — most tomboys don’t have role models of adult women who look/dress/act like them.
    This is a very long-winded comment but I have a lot of feelings about these two!!
    also yeah, i grew up to be a lesbian English major so no one will be surprised to hear that Matilda was my shit as a kid and I had/have a crush on Miss Honey.

  15. The scene in Little Giants where Ice Box is eating powdered donut holes out of the box in the grocery store is when I fell in love with movies – ugh so good. Also Devon Sawa (like JTT) was a very lesbian looking heartthrob.

    I would add Sonora from Wild Hearts Can’t Be Broken and maybe the whole cast of Little Women but especially Winona Ryder.

  16. a fellow Feature Films for Families subscriber over here!! Lol 😂 My mom didn’t want us to watch Matilda or Harriet the Spy bc they weren’t “Christian” and they involved “magic” and had “bad language” in them ☹️ (I often think about how different my growing up years would have been if I’d been allowed to watch movies that featured smart, independent, clever, tough, interesting, and complex young girl characters like Harriet and Mathilda.) We had SO MANY movies from Feature Films for Families and I remember most of them being pretty sappy and ridiculous. But Friendship’s Field! Omg Yvonne you just brought back so many memories for me!! Lol I remember thinking Ira was so cool, and I remember she picked on an older boy by saying “Did you get a free bowl of soup with that haircut Randy?” I didn’t get the joke at the time but I thought it was the coolest comeback EVERR.

  17. YES TO BECKY O’SHEA i love little giants so much AND MATILDA this is the best post tbh and you even got the absolute best line lily ever said in princess diaries yvonne how are you so great

  18. I grew up on the weirdest movies because my parents were Christian and tried to ignore any media made after 1985. But man my absolute favorite was Candleshoe featuring a young orphaned Jodi Foster in overalls. That movie gave me butterflies which I didn’t understand until decades later.

    Also this very weird movie called Girl of The Limberlost about a girl who is super sheltered and plays violin and collects insects. It really touched my violin-playing homeschooled heart and now I need to track it down for a rewatch!

  19. I’m a couple days late to this conversation but I have to add a few.

    Satisfaction (1988) – Justine Bateman, Julia Roberts, Britta Phillips, and Trini Alvarado as an all-girl band. YES PLEASE. I can’t even decide which of them I liked best, although Trini’s character Mooch was the most tomboy-ish. I somehow acquired a VHS copy of this when I was around 10/11 and I was fascinated by all of them for reasons I absolutely did not understand at the time.

    Mermaids (1990) – Winona Ryder as Charlotte Flax. I also liked her in Beetlejuice, but Mermaids is just such a good movie. Plus, Cher! Also bonus points for a baby Christina Ricci as Charlotte’s little sister.

    Camp Nowhere (1994) – Marnette Patterson as Trish Prescott. Her character was not a tomboy, she was the bitchy popular girl, but in my defense I was 14 and she was very pretty. And she turns out to be nice at the end, so.

    I also have to second (and third and fourth) Now and Then. I loved Christina Ricci, Thora Birch, and Gabby Hoffman equally. You can’t make me choose. I watched a lot of weird indie movies throughout the late ’90s because one (or more!) of the three of them was in it.

    Oh, and Bring It On. I was 19 and already fully aware of my queerness by the time that came out. I saw it in the movie theater. Missy & Torrance definitely had A Thing.

  20. So elated to see It takes Two on this list!! I definitely had a crush on Amanda but dreamed of being Alyssa. Also, low key Kirstie Alley? And that food fight scene in the mess hall!? Never have I wanted mac n cheese more.

    Side note, does anyone remember that movie the Olsen twins did about sea world with the orca music video at the end?

    (PSA: ITT is streaming on Hulu.)

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