When the tech scene turned their attention to websites for kids, they didn’t exactly know what they were doing. The boon of the dot-com bubble was mostly led by upstarts just out of college; there wasn’t much parenting experience split between them. As a result, early kids websites were offbeat, whimsical, occasionally missed the mark, and almost always entertaining. Case in point: Yahooligans! (later renamed to Yahoo! Kids).

Created in 1996, Yahooligans! was meant for the 10 and younger crowd. It mirrored the search engine and directory capabilities of the main Yahoo! site, but with a list of websites screened by the staff as suitable for grade school kids, and with a bright-colored and textured design that gave it a late-90’s Nickelodeon type vibe. It was extremely popular.

Building websites for kids was a choice, and a sound business decision. In the late ’90’s and early 2000’s, kids and teenagers accounted for a relatively large percentage of the web-going population, with some estimations putting people under the age of 18 using the web at over 30%. Kids are often early adopters of new technologies, and they were willing and able to sink time into the world of computers.

Some websites aimed to make that world a safe and respectable place to be. In 1997, librarians at the Rampo Catskill Library System in New York created a pre-screened search engine designed for young children. That project eventually expanded, with the help of Roy Tennant at UC Berkeley, into KidsClick! Every website listed in its directory of categories or through its search engine was approved by a librarian from the team.

An even more bespoke take on kid-friendly search came from a concerned father of four from the UK. He created the search engine Dib Dab Doo and Dilly too!. The mascots of the site —four cartoon animals with names pulled from its title—guided kids through a curated search experience filtered for educational, helpful, and safe content.

Dib Dab Doo and KidsClick! were soon joined by other kid-focused search engines, including Ask Jeeves for Kids, KidsRex, and Kiddle.

But search was only the first step. If kids were going to go online, the tech industry reasoned, they would need some games too.

By 1999, Yahooligans! expanded to include original games—board games, question and answers, and classics like Checkers and Go Fish—designed to be played by kids. “The site has been designed as an area where kids, parents, and teachers can interact, have fun, and compete in classic games they all know or have grown up with,” Yahooligans! managing editor Catherine Davis said when the games were first released. That content quickly expanded out into chat rooms, sports trivia, and a Dear Abby knockoff with the moniker “Ask Earl.” And all of it was tailored for kids.

The web games of the early 2000’s were an interesting visual compromise. Constrained by sluggish bandwidth and limited graphic displays, these games often blended low-fi production value with interactive game mechanics that promoted community and collaboration.

Sites like Neopets and Habbo Hotel set the tone for that level of interactivity. Players would create “homes” for themselves online, and interact with other players. When Newsgrounds and MiniClip began to make Flash games more popular it added a more dynamic and graphic element to online gameplay. Games on these sites thrived on viral success through word of mouth and clever twists on classic game concepts.

Club Penguin mixed elements from both of these trends. It didn’t necessarily have much of a mission or business goal; it was created as an ad-free space for kids to play in a virtual world. It had what would be in other online spaces draconian rules; no swearing, no bullying. Moderators policed the site for wrongdoing. There were no popups or call to actions, in fact, there was no advertising at all.

The game had a number of precursors dating all the way back to the late ’90’s, when game developer Lance Priebe began his decades long preoccupation with penguins. His first attempt was a penguin-filled Flash game, followed by a penguin-led virtual world and chat room known as Penguin Chat in the early 2000’s.

Priebe didn’t happen upon a winning penguin formula until he worked alongside two co-workers from his day job as a video producer, Lane Merrifield and Dave Krysko. Together, the trio created an experience they would want for their own children. Something social, immersive, fun, and most importantly, safe.

Club Penguin launched in October of 2005. When you signed up, you got to pick the penguin you wanted to be. Your home was your very own igloo. Using your penguin avatar, you could enter the virtual world of Club Penguin. There were games, chat rooms, and social events. It was a completely graphic world represented on the web, and players could explore various activities, talk to other players, purchase items for their penguin, and attend large virtual parties hosted by the games creators.

Lots of kids grew up playing Club Penguin, as formative to their youth as Super Mario was to the Nintendo generation. Players invented secret code languages (sometimes, to get around the no-curse rules), or created in-game challenges the creators never intended. Much like Neopets, creators invented an entire lore for the world inside of Club Penguin, one with elaborate fictional backstories and imaginative backdrops for adventures.

But what was always miraculous about Club Penguin was the loyalty of its followers. It was a first released to a small group of kids; around 15,000 people were using it in the first few months. That number grew to millions in just a couple of years, spread almost entirely by word of mouth and on the strength of the community. Even after it sold to Disney in 2007, Club Penguin kept its site safe.

It was this somewhat strange, and largely unfocused, environment that many kids came of age with on the early web. And it would shape their experiences for years to come.