Microsoft BOB

Billed as the only software a customer would need, Bob was both an environment to work in and a collection of Bob-specific applications designed to work in that environment. It included:
Letter Writer, Calendar, Checkbook, Household Manager, Address Book, E-Mail, Financial Guide and GeoSafari.

Bob accomplished a great deal during its near-immediate dive into commercial failure and obscurity. While widely criticized for its condescending tone and dumbed-down interfaces it was a groundbreaking piece of software for Microsoft.

The character-based user interaction (introduced for the first time commercially with this software) was the predecessor for the Floating Paperclip that began persecuting Microsoft Office users a few years later. End users were encouraged to interact with a help assistant as if it was a pet or a friend. This assistant would produce "helpful" suggestions in the form of content-specific messaging as well as reminding the user of bills to be paid or appointments to keep, etc. This more social interaction with the end user was a dramatic change for Microsoft, a company whose only previously released user-accessible interface came in Solitaire.

The second innovation came in allowing customers to customize the "rooms" that their assistants lived in. End users could recreate Graceland, move furniture around, change themes, etc..

While it was a clumsy attempt to personalize the beige box and hospital-cornered interface that Microsoft Windows had offered, Bob did present a dramatic shift into a new direction for Microsoft.