It was love at first smirk. On March 3, 1997, Daria hit MTV, sending shockwaves of sarcasm and snark across teen culture. With incendiary wit and a razor-sharp insight, this side-eying high schooler proved an inspiration to a generation that had the world at their feet, but suspected that was a trap. With idealism edged by cynicism, Daria became a beacon of hope for teens frustrated with student life rife with popularity contests, routine embarrassments, and choking vanity. She was too cool for such high school shenanigans, and cut through its hypocrisies using her wits as a weapon, urging fans to follow her example.

To celebrate Daria‘s twentieth anniversary, Nerdist reached out to the show’s co-creators, Susie Lewis and Glenn Eichler, to discuss its evolution, legacy, and its quintessential episodes. Exploring common teen experiences like insecurity, rebellion, sibling rivalry, crushes, finding community, and feeling like an outsider, these episodes distill the very essence of Daria.

“The Invitation”

Season one, episode two

After moving from Beavis and Butt-Head‘s hometown of Highland, the spinoff heroine settled into Lawndale pretty quickly. By Daria‘s second episode, she’d already scored an invite to the Brittany’s house party, full of popular kids like the lunkheaded Quarterback Kevin, overachiever Jodie, the Fashion Club, and even the sex-obsessed Upchuck. Viewers got an efficient tour through this high school’s hierarchy, and saw how Daria was a different from a lot of other teen shows. “I wasn’t thinking about this at the time,”Eichler says, “But it sets up that Daria isn’t being absolutely rejected from this world of the popular kids the way they do on most shows about high school. Instead it’s a case of benign neglect.”

“THE IDEA IS THAT IF YOU HANG IN THERE, THINGS WILL IMPROVE.” – GLENN EICHLER

And this neglect suits Daria fine. Surrounded by shallow teens fawning and flirting, she and Jane stood out early on, defined by their acerbic humor and preference for pranking the residents of Brittany’s gated community, instead of getting down with the Soul Train. (Beep beep.) To that end, Eichler tells fans to look out for how director “Karen Disher animated Sandi so she was doing a Snoopy dance.” It’s the move all the cool kids are doing.

“The Road Worrier”

Season one, episode 11

The first to focus on Daria’s fumbling flirtations with Jane’s brother Trent, this ep threw the crew into a busted van on the way to the Alterna-Palooza music festival. But what seemed like a chance to get cozy with her crush soon turns into a nightmarish string of embarrassments, from a bulbous bee sting to breaking her signature glasses and sitting on a sloppy sandwich. Still, it allowed both Daria and audiences to get closer to the beautiful but not-so-bright Trent Lane.

When it came to creating Daria’s first crush, Lewis pulled from her past. “I grew up loving music and loving the guys that were in the band,” she recalled. “A lot of them were really hot on stage, but when you talked to them, it was completely different. And it was such a bummer.”

Eichler noted the sweet but oblivious Jordan Catalano from My So-Called Life was an inspiration point. “He was this real dreamboat, right?” The co-creator explains, “But whenever he talked, he was kind of a moron. And I liked the idea that Trent was this really really hot guy, but–not a moron–but kind of flakey.”

Named after Nine Inch Nails’ Trent Reznor and modeled after smoldering guitarist Dave Navarro, Trent became an aspiring rock star whose laziness outsized his ambitions for his band, named Mystik Spiral (for now). “Then we decided he should be somebody who is in her life whether she wants him to be or not,” Lewis shares, “So the obvious connection there was to have him be Jane’s brother. Then the other twist is he’s not an asshole. He’s actually a really nice guy. And he’s really nice to her. And even if he says things that aren’t really bright, he’s still deep in a lot of ways.”

“Whenever they’re together, they have their moments,” Lewis says of the relationship, pointing to the end of this formative episode, where Trent bonds with Daria on the side of the road in a treasured private moment. “That was a real great moment. I love that she’s so shy and insecure around him. And he’s just nice.” He doesn’t mention the bee-sting, the taped up glasses, the sandwich goo on the butt of her jeans. “He doesn’t add to her anxiety. It’s brought on by her.” Simply put, you couldn’t ask for a cooler, kinder crush than Trent Lane. And like Daria, Daria fans fell hard from the start.

“The Misery Chick”

Season one, episode 13

When arrogant alumni Tommy Sherman abruptly bites it on the football field, Lawndale High students are forced to face mortality. So they turn, one by one to “the misery chick,” Daria. It’s a role that’s overwhelming and a bit insulting. In one of the series’ defining moments, the typically unflappable heroine explodes with a frank realization: “I’m not miserable. I’m just not like them.” Having written this ep, Eichler connects deeply to Daria’s irritation here.

“If you don’t smile constantly, people think there’s something wrong with you,” he declares. “And if something bad happens to a person you don’t know/care about, and you don’t act emotionally stricken, people think there’s something wrong with you. So to me, the point of that episode was there’s no reason to criticize her for the way she is. In fact, it’s perfectly valid, and in fact more honest than a lot of people.” Being honest in the face of peer pressure went on to become Daria’s brand, for better and sometimes worse.

“Arts ‘n’ Crass”

Season two, episode one

When a school-wide contest asks for poster submissions that represent “Student Life At the Dawn of the New Millennium,” Daria and Jane team up, pairing Jane’s painting of a pretty girl with Dara’s poem about how the social pressures to look pretty push its subject to bulimia:

“She knows she’s a winner / She couldn’t be thinner / now she goes in the bathroom / and vomits up dinner”

When Principal Li goes against their wishes and changes the poem to a more “upbeat” message–that just so happens to fly in the face of its intended purpose–the defiant duo concocts a Brittany-inspired plan to reclaim their controversial collaboration.

“THE GOOD GUYS WIN IN THE END, IF YOU CALL DESTROYING YOUR OWN ARTWORK WINNING.” – EICHLER

Over the course of the show, Daria would stand up to her principal’s mercenary style of administration on numerous occasions, from chasing off modeling scouts (“This Year’s Model”), to dropping the mic on radio shock jocks (“Jake of Hearts”), and souring the school’s deal with a cola sponsorship (“Fizz Ed”). But of all these episodes, Eichler called “Arts ‘N’ Crass” a personal favorite, sharing, “I just think that one takes a realistic look at censorship, and offers a pretty good example of adult hypocrisy and authoritarianism, e.g. telling kids to express themselves and then freaking out when they do. Plus the good guys win in the end, if you call destroying your own work of art ‘winning’.”

Another part that stands out to Eichler is how “Helen rides in to the rescue,” using her gravitas and legal know-how to defend her daughter against Ms. Li’s threatened retributions. High-strung Helen and deadpan Daria rarely saw eye-to-eye on the series. But in moments like these, teens at home got a welcomed reminder that their parents are people too.

“I Don’t”

Season two, episode four

Whisking the Morgendoffer clan off to a cousin’s country club wedding, this romp-com forced Daria into a criminally ill-fitting bridesmaids dress, saw Quinn getting hit on by an odious minister, and introduced “cool” Aunt Amy, a role model kicking back in Daria’s own family tree.

“We wanted to show that just because the people in Daria’s world think she’s weird,” Eichler explains, “doesn’t mean she is weird.” Aunt Amy was a sign of hope and a road map to adulthood for the oft-frustrated misfit. As to how the character was developed, Eichler essentially reverse-engineered from the personality of Daria’s hard-nosed mom.

“JUST BECAUSE THE PEOPLE IN DARIA’S WORLD THINK SHE’S WEIRD DOESN’T MEAN SHE IS WEIRD.” – EICHLER

He mused, “Helen is so uptight and so concerned with making sure everything is done correctly that I definitely could see her as the second in line where the first was a hippie, where the first had no sense of responsibility.” From this, the writers created the mother-of-the-bride, Aunt Rita, subject of a decades’ long sibling rivalry that would explode in an forgettable reception, complete with much brawling and bottle-swigging.

“So if Helen’s going to be the uptight one,” Eichler reasoned, “and her older sister is going to be irresponsible, I could see Amy not having to be part of that cycle. She becomes whoever she’s going to be. And also, I don’t think it’s particularly outrageous that Helen’s sister might have some of the same personality traits as Helen’s daughter.” When the two share a smile, wearing similar glasses, viewers got to share in that recognition.

“Monster”

Season two, episode six

Sibling rivalry between Daria and Quinn is front and center in episodes like “Speedtrapped,” where the pair roadtrip and meet a conniving cowboy, and “Quinn the Brain,” where the bubbly redhead won sweeping praise for one half-decent essay. (“There are different standards for cute people,” Jane quipped.) But the most defining of these centered on “The Depths of Shallowness,” a video assignment Daria made about the “hollow self-centered ego-maniac” that is her younger sister.

“I KIND OF SEE QUINN AND DARIA AS THEY GET OLDER, JUST BEING GOOD FRIENDS AND SISTERS.” – SUSIE LEWIS

As Quinn devotes herself to being pretty, popular, and pursued by boys, her intellectual older sister hoped to expose the vapidness of that way of life. And Daria hits exposé pay dirt when the preening teen queen has a meltdown on camera. (“My pores are cute! My pores are tiny!“) But after an odd but earnest confession from Quinn, Daria changes the cut to save her sister from social ruin. Naturally, it makes the Fashion Clubber even more popular.

Asked about “Monster,” Lewis laughed warmly, and quickly comes to Quinn’s defense. “I love Quinn. I always identified with her as well,” She explains. “I love fashion and I care about make-up, but I’m also very much like Daria and Jane, where I care about art and being introspective, and being deep and all that stuff. Quinn wasn’t dumb…she was just an average teenage girl. She loved what she was into.” Lewis went on to speculate about how Quinn would have continue to grow after the season wrapped, saying, “I kind of see her and Daria as they get older, just being good friends and sisters. And kind of coming to respect each other’s lives. And they’re different, but they’re sisters, so they’re bonded. If I had a sister, that’s how I’d want it to be.”

“Write Where It Hurts”

Season two, episode 13

Fans actually got a peak into what such a future might look like in the playful episode where Mr. O’Neill challenges Daria to compose a story based on people she knows. There are some fun nods to Jane Austen’s novels and a parody of The Graduate that has Jane running off with dunderheaded Kevin. But the last story is the one that really stuck with fans.

In it, Daria imagines where the Morgendorffers’ lives might be years down the road. Her parents, Helen and Jake, are calmer and content. Quinn has mellowed too, becoming a mother who channels the energy she once put into being popular into raising her rambunctious brood. And Daria pictures herself a happily married and successful writer, who is respected, loved, and understood by her family.

“What I was trying to do was give the character some light at the end of the tunnel,”Eichler says of writing the heartfelt episode. “And to teenage viewers, who were also having their own issues, I’m sure that they identified with that. That whole “It Gets Better” campaign (the anti-bullying campaign that reached out to LGBTQ youth) was essentially the same thing, only to a much more distressed portion of the population. The idea is that if you hang in there, things willimprove. I think I was trying to show that would be true for her, and I think viewers said, ‘Oh, maybe that’s true for me.’”

“Depth Takes a Holiday”

Season three, episode three

During the show’s third season, Daria‘s success inspired Eichler and Lewis to take bigger risk with their stories and format. It’s where they dove hard into camp and fantasy with a mirthful misadventure in which Daria helps anthropomorphized teen holidays, Valentine’s Day and Saint Patrick’s Day recover some truant peers (Christmas, Halloween, and Guy Fawkes Day), who’ve left Holiday Island High School in favor of joining Trent’s band, Mystik Spiral.

The break from the show’s established world and canon was roundly rejected by fans, earning”Depth Takes A Holiday” the dubious honor of being dubbed “the worst” of the series. But Eichler has a soft spot for its willful silliness. “It was so stupid in a good way,” he argued with a chuckle. “Where she meets Guy Fawkes Day? I mean come on, how often does that happen on TV?”

“Daria!”

Season three, episode seven

Conversely, when this season’s adventurousness spun Daria into a musical, fans were stunned but ultimately thrilled. “That’s my favorite episode,” Lewis gasps over the gleeful special that has all of Lawndale bursting into song as a massive storm threatens to blow the whole town away. Even Daria sang. Sort of.

“I knew right away that Daria didn’t have to sing. She could just speak through the words,” Lewis recalls. “But Tracy [Grandstaff, who voiced Daria] could actually carry a tune a little bit. As much as she spoke through it, it was fun. It was exactly how her personality should be singing. ”

Around this time, series like The Simpsons, Xena: Warrior Princess, Northern Exposure, and Ally McBeal were all churning out special musical episodes. As they headed into Daria‘s third season, this trend inspired Lewis, who grew up taking family trips to Broadway. “I was just like, ‘We have to do a musical.’ And I remember Glenn just laughing and being like, ‘What?!’ And he was like, ‘What would happen?’ Well, I was like something dramatic has to happen for it to be a musical. So, let’s say it’s a storm.”

From there, Lewis tapped musicians close to the show–including Eichler who plays guitar–to write the lyrics and music. “And as far as the actors went, that was just pure luck,” she laughs, noting how most could actually sing. “And even when they didn’t know how to sing well in character, it was funny. If it made us laugh, it was just good to go!”

The playful lunacy of the ep threw some viewers for a loop. But over the years, this playful twist on Lawndale has become a campy fan favorite.

“Jane’s Addition”

Season three, episode 13

But the biggest risks hit in the season three finale. Jane got a boyfriend, and Daria got over her crush on Trent. When the girls have to put together a multi-media project for class, they depend on the lackadaisical Lane sibling to compose some original music. But as Jane gets distracted with her new beau Tom, Daria realizes Trent’s let her down. Moreover, even though she still likes Trent, the two would never work as a couple. A thinly-veiled conversation about the class project hit Daria/Trent shippers hard.

Trent: I guess it wasn’t such a great idea for us to get together…on this.

Daria: No. I guess there’s no way it could have worked out.

Trent: It’s too bad, Daria. I always kind of felt you understood the way I think.

Daria: I do, Trent. I do.

Lewis remembers closing this door on Daria and Trent being “very meaningful,” noting that in a way it marked Daria growing up and “facing reality a bit.” Despite Trent’s flakiness, “he tries to be thoughtful.” So even though Daria made dumb moves like biting her tongue or getting a belly button ring to impress him (“Pierce Me”), “she kind of redeems herself by being attracted to him throughout the whole relationship.”

“SOMETIMES THINGS DON’T WORK OUT, NO MATTER HOW GOOD HE LOOKS IN A LIME GREEN T-SHIRT AND GOATEE.” – LEWIS

While it was a bittersweet goodbye, the Daria team managed one that respected each character, making neither the “bad guy.” It’s just sometimes things don’t work out, no matter how good he looks in a lime green t-shirt and goatee. “Yeah, isn’t that how it always is?” Lewis laments with a laugh.

“Dye! Dye! My Darling”

Season four, episode 13

In season four’s finale, tensions over Tom came to a head when when Jane demanded Daria dye blonde streaks into her hair. The result was less “the lady or the tiger” and more grim, spurring further fighting between the two. Then Daria kissed Tom, throwing the future of her friendship into peril. For Eichler, crafting the arc of all this upheaval was a challenge and a joy.

“To this day there are still issues with that whole thing.” Eichler confesses. “My feeling was we’d gone a number of years; Daria hasn’t had a boyfriend and hasn’t had anything remotely romantic. She really hadn’t dated to any extent. I felt like maybe the fact that I don’t want to write about her having a romance isn’t enough justification for her not to have one. But I also felt like in a situation like that, someone that shy and non-social, the way she might be most likely to meet a boy would be if it were the boyfriend of a friend, and of course that would mean Jane’s. So that’s how that got constructed.”

While shaping the Tom arc that’d stretch through the rest of the series’ run was tricky, Eichler describes writing Daria and Jane’s big fight here as “a nice change.” He explains, “anytime the relationship between two characters changes, you get to write stuff you haven’t written before.”

The DIY dye job was basically Jane’s way of pushing a conversation she and Daria needed to have about Tom, but both were avoiding. “Jane was always more emotionally mature than Daria was,” Eichler remarks. “She certainly moved in and out of teenage society better than Daria did. But her view of the world was the same as Daria’s, but she took it with more good humor. And I think she enjoyed how funny Daria was about expressing that shared view.” This shared view is ultimately what would pull the smirking duo back together through the end of this episode, and the subsequent TV movie, Is It Fall Yet?, which served to bridge seasons four and five.

“I knew they wouldn’t be permanently estranged,” Eichler says, “because they were too close. They needed each other too much, and they complimented each other too much.” And as the series drew to a close, Daria would need her best friend more than ever.

“Boxing Daria”

Season five, episode 13

In a stunningly snark-free arc, an abandoned refrigerator box reminds Daria of a frightening formative moment from her childhood, one where her parents nearly split up, and she and Quinn were all too aware of why.

Reflecting on how her rebellions and failures to fit in have affected her parents, Daria sinks into despair, and into the box in the backyard. It’s a frank yet tender heart-to-heart with her most trusted friend Jane that urges her to have a tough but tremendous parent-child talk. Ultimately, this discussion pulls her back out, thanks to some insightful words from her mom and dad:

Jake: It was part of the deal. It was the other side to you being so smart and perceptive.

Daria: What do you mean?

Helen: Daria, you can’t have a child with your kind of intelligence and expect her to fit in easily with other kids. We weren’t happy to be called into school because we knew it meant you weren’t happy.

“It was just about how do people end up being the way they are,” Eichler explains. “It’s nature and it’s nurture but there are also defining episodes of their lives. And you know, I was obviously very fond of the character and I wanted to approach her with the most compassion that I could. And I thought that’s what happened there.”

While the series officially ended with the playful movie Is It College Yet? the season five finale is what many fans–and Eichler–consider the true conclusion to Daria. “It was good way to button up the series. Like the movie ended the series, but so did that episode.”

“I WAS VERY FOND OF THE CHARACTER, AND I WANTED TO APPROACH HER WITH THE MOST COMPASSION THAT I COULD.” – EICHLER

“I think “Boxing Daria” was a more appropriate end to the series.” He considered, “I think Is It College Yet? was a more fitting look to the future, and I think those are kind of different things.”