Interface Invaders
The latest from the "Cranky User": Everything I need to know about usability, I learned at the arcade makes some excellent points.

"Many video games are designed so that the user doesn't need to be taught how to play; the designers assume that the user will never read the manual. Modern games often feature some kind of tutorial before the game really starts, to expose you to the concepts you need to be familiar with in order to play the game well. To be frank, productivity software is often hostile to new users. Help systems are either absent, poorly designed, or just plain wrong. Even companies like Apple, who have built a reputation for usability, can get this wrong; Apple's AppleGuide help system, for instance, won't let you read the instructions for performing a task unless you perform them as you read through them. Its mantra of "do this, then click 'continue'" is a distressing one."

Classic video arcade games I remember playing a lot (dating myself): Dig Dug, Defender, Spy Hunter, Galaga, and Tron

Classic PC software you might have missed: Oregon Trailer Trash, Mavis Beacon Teaches Quilting, and Microsoft Bob