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The online hangout where millions of kids waddled around as cartoon penguins, decorated their igloos, adopted puffle pets, and played mini-games for coins in a safety-focused chat environment. Club Penguin was one of the first MMOs designed specifically for kids, and it became an after-school addiction that defined a generation's online childhood.
The web filter loophole that became a school institution. Cool Math Games' "math" branding kept it off the blocked-site list while every other gaming site got nuked, making it the de facto arcade of every school computer lab in the mid-2000s.
A turn-of-the-millennium site where you played games for a shot at cash, with a $10,000 drawing every Wednesday afternoon and winnings that landed on a funCard MasterCard. It was live by early 2000, folded in the dot-com bust of 2001, and is remembered now mostly as the $3.9 million failure Nick Woodman had before he built GoPro.
General Mills' cereal-box virtual town: make a character, earn Millsbucks, furnish a house, and play arcade games named for Reese's Puffs and Lucky Charms. Millsberry ran from 2004 to 2010, the fullest advergame of its era, and signed off by handing every citizen a yearbook.
Disney's kid-safe MMO let kids become a cartoon dog or duck and fight the Cogs, gray robot businessmen, with cream pies and seltzer bottles. Toontown Online launched June 2, 2003, at $9.95 a month, kept chat to a menu of approved phrases, and closed on September 19, 2013, which is roughly when the fans started rebuilding it themselves.