The conversation about female friendship was so different in the '90s. It was the era of the mean girl, when stories on film and television didn't necessarily focus on women and girls having each other's back in an evolved, #friendshipgoals, good energy kind of way. Eventually, the characters would (almost) always end up supporting each other, but the path they took to get there was riddled with eye-rolling judgment. Frenemies were everywhere: Stealing your boyfriend, racking up a crazy bill on the phone (that plugged into the wall), introducing you to psychopaths who intend to murder your family, and being general narcissists. In honor of Winona Ryder's (one of the best of the worst, who's also been on the receiving end) 45th birthday today, here are the worst best friends of the '90s in order of "pretty bad" to "homicidal."

10. ABBY: The Truth About Cats and Dogs (1996)

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In a twist on the classic Cyrano de Bergerac, Abby, an insecure vet with a radio talk show (Janeane Garofalo) forces her best friend Noelle (awkward but gorgeous Uma Thurman) to go out with a regular caller who she's into but has never met IRL, and tells her to pretend to be her. You can guess the rest. Worst friend moment: Predictably, Abby gets mad at Noelle for sort of liking him, and mopes incessantly about being short.

9. RALPHIE: Welcome to the Dollhouse (1995)

In this '90s masterpiece, Dawn Weiner (brilliant Heather Matarazzo) is the ultimate awkward teen: universally loathed at school, overshadowed at home by a perfect little sister, excruciatingly awkward. Dawn is screwed. Her best friend and the only other member of the "special people club" is Ralphie, a wisp of a boy who stands by silently as people torture her. Worst friend moment: In what may be his only line of the film, Ralphie tells Dawn's tormentors, "You think you're hot shit, but you're really just cold diarrhea," which is the least effective comeback of all time.

8. SIDNEY: Scream (1996)

What is now a classic horror film was once a quirky, unexpected slasher flick about a serial killer who offs hot teenagers in a small town (creator Kevin Williamson says that it was inspired by the same event, The Gainesville Ripper murders, that inspired my book, The Drifter). Sidney (Neve Campbell at her whiny best) is a terrible friend for one reason, and that is that everyone she likes, even a little, dies a violent death. Worst friend moment: Sidney's BFF Tatum Riley (peak Rose McGowan) is killed in the garage while looking for beer or something at a party, and Sidney doesn't hear her blood-curdling screams because she is cozy with Skeet Ulrich inside.

7. JULIE: Felicity (1998)

The only thing about this show that was worse than Keri Russell's season-two haircut was Julie (Amy Jo Johnson). As Felicity's tiny best friend, Julie was dead-eyed and dull. But being boring wasn't even her biggest offense. Julie actually believes Felicity when she says that she is over stalking Ben (Scott Speedman in his finest hour), the guy she followed across the country to college. Worst friend moment: Julie dates Ben for the better part of a season. A close second: Every time the camera cuts to her expressionless face.

6. KELLY: 90210 (1990)

Yes, Brenda Walsh (Shannen Doherty) was an incredible bitch. And some may say that she had it coming. But Kelly (Jennie Garth at her blondest) crossed a line when she fell in love with Brenda's boyfriend, Dylan (Luke Perry at his tiniest). In an interview from 2012, Doherty confessed that she was baffled by the turn of events when she read the script. "I thought that it was really wrong that we were putting that out there, that we were saying, 'Yes, it's okay for a best friend to fall in love with her best friend's boyfriend and cheat with him.' Where's loyalty, where's friendship? And isn't loyalty the most important thing in this world?" Mic drop. Worst friend moment: When Brenda answers her front door (wearing a VERY '90s black leather vest) to find smug-faced Kelly and Dylan, who then break the news about their relationship. It still hurts.

5. RAYANNE: My So-Called Life (1994)

Angela Chase (adolescent Claire Danes) was the angstiest of all angsty high school girls, constantly journaling and casting moody glances at her sort-of boyfriend Jordan Catalano (Jared Leto two decades pre-Oscar and iffy band). And Rayanne Graff (A.J. Langer) was the ultimate, predictable sidekick: She had a single mom, self-esteem issues, a taste for alcohol swigged directly from bottles, and extreme accessories. You know that the wheels are going to fall off this friendship from the first minute you see them together on screen. But that doesn't make it less painful when you see needy Rayanne make the moves on Jordan. Worst friend moment: When the nerds from the school paper tell Angela that Rayanne and Jordan got wasted and hooked up in the parking lot of an all-ages club, possibly in the backseat of a car.

4. MARGO: Fear (1996)

Knowing the 2016 version of Reese Witherspoon makes it hard to picture mid-'90s RW playing a rebellious but still innocent teenager (Nicole) in Grunge-era Seattle. But Alyssa Milano as Margo, her trashy, tiny skirt-wearing, lip-liner loving BFF? That's sort of a no-brainer. When Margo gets Nicole entangled with some incredibly gross but kinda hot criminals (including Mark Wahlberg as David, Nicole's boyfriend and a total thug, which is just how things used to be), things get weird. Worst friend moment: Margo neglects to tell Nicole that her new BF has Borderline Personality Disorder.

3. LAURA: Walking and Talking (1996)

Director Nicole Holofcener's first movie, a quietly perfect little indie about best friends Amelia (amazing Catherine Keener) and Laura (Anne Heche), is arguably the best movie ever made about the odd quirks of female friendship. When self-involved Laura is consumed by her impending wedding, she ignores Amelia, who struggles with the transition and the death of her cat—who falls off a fire escape onto a Brooklyn sidewalk. Dark. Liev Schreiber as a silly ex-boyfriend is a total bonus. Worst friend moment: When Laura leaves a message on Amelia's answering machine asking if she hooked up with "the ugly guy," who is in her apartment and hears it, in a plot twist that was forever ruined by voicemail.

2. LELAINA: Reality Bites (1994)

Oh, Winona Ryder. We will love you forever regardless of, or maybe BECAUSE of, how many times we watched you be a bad friend on screen. As Lelaina, she is the worst: Condescending, spoiled, mean-spirited, and lost. She is horrible to snarky Vickie (again, Janeane Garofalo) and aimless Troy (Ethan Hawke, in his coffee-and-cigarettes milieu). And she only sort of redeems herself at the end of the most '90s of all movies. Worst friend moment: When she parks herself on the couch for a month and racks up a $400 phone bill (calculating inflation, roughly $600, which 😲) calling the Psychic Friends Network, which was an actual thing.

1. NANCY: The Craft (1996)

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From a fashion perspective, The Craft—which is about a coven of high school witches—won the '90s. Dark lipstick, leather chokers, over-the-knee socks…it's all there. Sarah (Robin Tunney) moves to L.A. and stumbles into a trio of Goth girls who are into the occult (because, duh, who WASN'T?). And then they discover that together, the four of them have dark magical powers. As Nancy, Fairuza Balk brings the crazy in the most spectacular way. You just know that someone is going to burst into flames at any second. Worst friend moment: When Nancy kills Sarah's boyfriend, sending him plummeting out of a window while she screams her head off. It's a classic.

Christine Lennon is the author of the upcoming novel The Drifter, which is available for preorder here.