Oh man, it’s been so long and I tried so many that I can’t possibly offer a certain answer… but a good candidate is JumpStart Preschool, which I (barely) remember playing on a Windows computer. Otherwise, it could have been The Busy World of Richard Scarry Busytown, Richard Scarry’s How Things Work in Busytown, Gus Goes to Cyberopolis, Fisher-Price Ready for School: Kindergarten, Fisher-Price Learning in Toyland, Fisher Price Great Adventures: Pirate Ship, or Nick Jr Play Math!
There are many more that I could name, like Oddballz, Pajama Sam in No Need to Hide When it’s Dark Outside, Ozzie’s World, Sesame Street: Numbers, Mr. Potato Head Activity Pack, Play-Doh Creations, and Candy Land Adventure, but I am less sure of those. Finally, there are those titles that I simply can’t find again. There was a point‐and‐click program that mainly took place in a spaceship, and another one where a character said ‘I brush my teeth before I go to bed every night!’, but I’ll be damned if I can find videos of those.
I shouldn’t have chuckled at this.