Like many of the best animated series, Smiling Friends revels in adult darkness while looking like it was made for kids. Even its name could sound creepy or wholesome depending on your mood.

The Adult Swim show, which is airing a special episode tonight, follows two Smiling Friends employees—sunny Pim and cynical Charlie—who, at the behest of their boss, Mr. Boss, are given a simple task: Make clients smile. The pair seem to have no training, and often encounter bleak circumstances: In the pilot, they attempt to cheer up a man who constantly holds a gun to his temple. By the show’s seventh episode, a rival company, Frowning Friends, has set up shop across the street. (“I get it Pim, they’re the bizarro versions of us, but what’s the endgame? It’s just pissing me off now,” complains Charlie). It’s much easier to make people frown than it is to make them smile, and the new outfit draws a crowd, promising to reveal “the brutal cruelties of reality.” Frowning Friends’ grotesqueries, however, turn out to be stock footage of military marches and burning trees. “Is this really supposed to be …” Charlie says. “I’ve seen way worse on the internet.”

To be sure, much of Smiling Friends’ darkness, and humor, comes from the internet. Animators Zach Hadel and Michael Cusack say that the show, and that joke specifically, are throwbacks to a time when the web felt unfiltered—when it felt scary and chaotic and thrilling. Smiling Friends is steeped in early and mid-aughts internet animation and humor, a time when colorful cartoons about bopping badgers spread like wildfire and kids had to install the latest version of Flash Player to keep up. When being 12 years old, says Hadel, meant going to your friend’s house and having them show you the worst video they could possibly find. When kids crowded around a computer and beat up a digital George W. Bush, and braved shock sites like Meatspin, Lemon Party, and Rotten.com, the gore site that hosted pictures of dead people. “Rotten.com was the first website I went on,” Cusack says over Zoom. “I must have been seven years old or something—that’s fucked. It’s not good. Or is it? Maybe it is?”

Both Cusack and Hadel grew up in this era, and it’s also when they learned to animate. Cusack, the younger of the two, started making cartoons as a kid, but in his early twenties he began watching YouTube tutorials on animation and uploading shorts to the site; he’s produced his own show, YOLO Crystal Fantasy, and a parody episode of Rick and Morty. Meanwhile, Hadel, known online as Psychicpebbles (and the world’s strongest gamer), was building a following with viral Skyrim animations, the web cartoon Hellbenders, and video game Let’s Plays.

“He’d been animating for much longer than me and was a bigger personality on YouTube for animation,” Cusack says. “But we both had a similar goal to do TV. So we just teamed up and would work together and come up with projects, and Smiling Friends was one of them.”

Like so many artists, Hadel got started on Newgrounds, a haven for games and animation. For occasional visitors, Newgrounds was infamous for animated celebrity deaths and violent stick figures, but insiders knew where to find the good stuff. If the internet back then was a Wild West, Flash Player was the six-shooter, and Newgrounds the saloon. “At some point, I started seeing stuff get uploaded there that was on par with what was on television and even better in terms of the quality,” Hadel says. This friendly “cold war” between animators was inspiring. It was incredible to see whole cartoons—the music, voicing, writing, and animation—completed by one person. “I remember being as excited for a Tomorrow’s Nobodies episode as I was for Family Guy episodes,” says Cusack. What excited him was that both were equally important in his 14-year-old mind, but “one cost millions of dollars and one cost literally zero!”

If you pay attention to the show’s guest voices, you’d see this influence. Sick Animation’s Marc M. plays the boss, and superstar of the Flash-era David Firth voices a lovelorn shrimp. Some shows would go for Hollywood actors, explains Cusack, but they go for internet people. They want to bring together more extremely online guests next season, but Cusack smartly cuts Hadel off before he can tell me who.

Like Flash cartoons, Smiling Friends episodes are short, about 11 minutes, and meant to be watched and rewatched. These aren’t “high IQ episodes,” explains Hadel, who says he slept during art class. They feel rambling and improvised. They aim to entertain rather than educate, unlike some shows that meditate on their dark subject matter in a philosophical or therapeutic way. It’s easy to detect shades of early South Park, another program that could look like a kids’ show to a glancing parent but was decidedly not. They’re just trying to have fun with the darkness. “In this world, we can have the Newgrounds humor, but it doesn’t feel dark, it doesn’t feel scary,” Hadel says. “It’s got a colorful gloss over it. It’s like getting the best of both worlds.”

The pair use Adobe Animate, the software formerly known as Flash, and there are moments where you see aesthetic similarities to mid-aughts animation, like a person’s head casually being stomped into bloody lo-res goo in a grimy hallway background. At one point, a pair of characters, “the Fun Twins,” scream and dance about the screen. Hadel cites what he calls “spam cartoons”—those overly loud, flashy animations that used to crash desktops—for the show’s intentionally abrasive sequences.

Juxtaposing stuff like this against more sophisticated animation was a big deal for the duo. The show features a mix of species—the boss is a thin-limbed human; Pim and Charlie are lavender and yellow blobs—as well as animation styles. At one point there’s even a full-on 3D alien, 3D Squelton. “Even the idea of a 3D character coexisting in the same world as a 2D character, and 2D characters who don’t look necessarily like they’re from the same place,” says Hadel. “I would say even that is influenced by the idea of having a website where you’ve got an infinite amount of unique art styles.”

Even the show’s style of humor can feel like internet trolling. This weekend’s special, which begins and ends in an airport, thumbs its nose at the audience, or at least at the format of specials. That’s the point. “We hope people will realize that they’re getting the rug pulled out from under them, and enjoy it for the reason they didn’t think they would enjoy it,” says Hadel. “But also, if you don’t enjoy it, that’s kind of funny.”

Both creators admit their nostalgia for that era of the web, back when Newgrounds’ motto was still “The problems of the future, today,” and when things felt chaotic and amateur rather than clean and businesslike. Back then, Hadel says, the only rules were those dictated by the forums you were on, and there wasn’t as much “cynical corporate stuff masquerading as amateur.”

It’s true that, back then, our minds seemed like glass, liable to shatter at a visit to the wrong website. Like Charlie, it’s harder to shock people now. They’re burned out and cynical. Perhaps they just grew up. Still, Smiling Friends is a reminder of a simpler web, back when the “brutal cruelties of reality” were the gore JPEGs that lived on Rotten.com. Now things are cleaner, but a different kind of horror prevails, and feels inescapable. Just log on to social media. It would be easy to say that Cusack and Hadel’s trick is just tapping into collective nostalgia for Flash, but it’s more than that. It’s tapping into an internet that no longer exists.