The ’90s Tomboys I Had it Bad For


As a child of the ’90s, I grew up consuming a lot of pop culture about girls my age or just a bit older. Although tomboys have been a part of TV, movies and books, it felt like most of my favorite things to re-watch or re-read had one among them. At the time, of course, I had no idea why that was, especially considering I was not a tomboy myself. But now it’s very clear to me I was hardcore crushing on these girls and, in some cases, my unknowing gaydar was not far off.

Roberta, Now and Then

Christina Ricci played a softball-loving tough chick who taped her boobs down and wasn’t afraid to throw a punch if a boy disrespected her. I was so mad Christina kissed Devon Sawa, as were all my other girl friends, but they were jealous of Christina. I thought Roberta should be kissing Samantha (Gaby Hoffmann), and it all came full circle when I grew up and found out Pretty Little Liars creator Marlene King had written the movie and also intended Roberta to be a lesbian. It’s also worth mentioning that Rosie O’Donnell played the older version of Roberta.

Busy, Ready or Not

Ready or Not played on the Disney channel and I thought it was the coolest show that no one else I knew watched. Busy and Amanda were BFFS, and Busy was a tomboy with a capital T. She was into sports and skateboarding and was so pissed when she got her period. It was so clear that she was crushing on boy crazy Amanda, and she hated whenever Amanda had a boyfriend. (So did I.) The actress who played Busy (Lani Billard) is now an out lesbian.

Darlene, Roseanne

Sure, Darlene spent a lot of time with David, but all of her flannel, sarcasm and vegetarianism had my attention. She wrote short stories, poetry and comic books, and she moved to Chicago to go to art school. I mean, she was essentially everything I never knew I wanted. As we all know, Sara Gilbert is gay, even though Darlene was not.

Icebox, Little Giants

That damn Devon Sawa. He ruined everything for me in the ’90s. Icebox wanted to play football but the local peewee team scoffed at her want. She starts a new team with some other misfits and, of course, the Little Giants end up making some wild plays to win the big game. There’s one scene with Icebox where she’s watching Devon Sawa flirting with cheerleaders at a car wash and I liked to think she shared my feelings about his being un-worthy of all the female attention he received. Actress Shawna Waldron went on to partake in some lesbian kisses in Poison Ivy: Secret Society. Devon Sawa was not involved.


Before Ciara paired slouchy pants with a sports bra, there was Aaliyah in Calvin Klein men’s underwear peeking out of her low-slung jeans or folded-over overalls. I loved her hoodies, hats and sunglasses and the way her sultry alto voice slunk along songs like “If Your Girl Only Knew.” Plus she paled around with Missy Elliott and the combination was the reason I spent so much time watching MTV in middle school. Sadly Aaliyah passed in 2001, but I feel like she would have been a great ally and continue to produce music I’d vibe to. Her style inspired so many others so she lives on forever.

Kristy, The Baby-sitters Club

I was an avid fan of the entire series of books, but I also enjoyed the VHS tapes of The Baby-sitters Club TV show — largely in part because of Avriel Hillman, who played Kristy. She was not only a softball player (sensing a theme here), but the President of the BSC, meaning she was bossy and kept all the other sitters on point. Kristy was not interested in boyfriends and I always kind of wanted her to spend more time with Stacey, the fashion-forward city girl who lived in Stoneybrook with one half of her divorced parents. Instead Kristy’s BFF was Mary-Anne, who had a boyfriend named Logan. I thought he was boring.

Tori, Saved by the Bell

Besides being very confused that Kelly Kapowski and Jessie Spano seemed to have vanished from Bayside for all of senior year, I was also perplexed by biker chick Tori’s affection for Zach Morris. He just didn’t really seem like her type. His nickname was Preppy, after all, and Tori was a tough bad girl with an interest in fixing cars and teasing her hair. In real life, Leanna Creel is now married and she and her wife Rinat Greenberg have a five-year-old son. Sorry, Mark Paul-Gosselar.

Obviously not all tomboys are lesbians, but there’s no denying they are my kind of girls.

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