My first would be getting a Nintendo (NES) from Target. I think it was $129.99 and playing Super Mario Bros, literally every day after preschool. I never beat the game (final castle in World 8 was a repeating maze that I never got past), but it brings back a lot of memories of just playing it until I died.
I also had an Apple II GS computer back in the day, that had some fun, educational titles as well. Mother Goose was one that I have fond memories of playing. You basically go around finding different nursey rhyme characters' items that have been misplaced, and once you find the item and bring it back to the appropriate character, they play a small sequence from it.
What about you guys?