When you were little, NO ONE was cooler than your babysitter. She had shiny hair, probably a boyfriend, and you equated her with contraband TV, pizza, and a lack of parental supervision. While we all had our own real-life versions of the Cool Babysitter, these are the on-screen ones: those heroines of sixth grade sleepovers who defined cool and made up a fictional sorority of inspiring, independent young women. 

They taught you how to talk to your friends about eating disorders, throw water balloons at boys, and some of them made even the straightest of arrows pause when mom sat you down at the kitchen table for the gay is okay talk. As the awesome Headmistress of St. Godard’s, Miss McVane, says in Strike!, “They’re not just girls, they’re you.” Albeit with better catchphrases. Here are our heroines from a time when there was nothing we liked better than gorging on estrogen, M and Ms, and popcorn. 

1. Thora Birch in Ghost World 
With her hodge-podge vintage wardrobe, perma-sarcasm face, and black bob, Enid was the poster-child alt heroine. Would that we could all respond to perky classmates and well-meaning authority figures with a completely disinterested withering glare, then go home and dance in our bedroom wearing a kimono. 
2. Christina Ricci in Now and Then
The ultimate tomboy. We can’t think about which Roberta moments are better: when she hits a home run at the baseball game, takes revenge with waterballoons and underwear stealing, or has her first kiss with Devon Sawa and then threatens to beat him up if he tells anyone. And the seventies style-denim pedal pushers, baggy plaid shirts, and an awesome bicycle-can’t be beat. 
3. Kirsten Dunst in Strike! 
Vereena and her henchwomen Tinka, Odie, Momo and Tweety were the ultimate boarding school rebels, taking down lecherous teachers, being stalked by townies, and eating ravioli. They were girls who wanted more than to be “finished,” aka grow up to be a housewife with a collie and a white picket fence. They were going to be successful, and help each other along the way: sisterhood of the travelling kneesocks. NO MORE LITTLE WHITE GLOVES! 
4.  Rachael Leigh Cook in The Babysitter’s Club 
The peppy do-right sisterhood of The BSC (as well as those checkerboard bookcovers) are incredibly iconic. What girl didn’t dream of taking over the neighbourhood with her own entrepreneurial gang of Best Friends? While all the girls in the movie gave us a reason to love them, it was Mary Anne’s preppy style, fierce loyalty, and quiet poise that left a lasting impression, made us want to buy a horse, and wish we had a stepsister from California. 
5. Winona Ryder in Heathers 
“Fuck me gently with a chainsaw.” WTF just doesn’t have the same ring, does it? Winona keeps her shit together in the face of mean-girl murders like no one before or since. 

~ Haley Cullingham