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Love him or loathe him, Clippy was impossible to ignore. That bespectacled, wire-formed assistant would pop up uninvited, cheerily asking, "It looks like you're writing a letter. Would you like help?" For millions, it was their first experience with intelligent assistance—buggy, intrusive, and oddly endearing. Clippy became the mascot of an era when software tried, often clumsily, to be a collaborator rather than just a tool.

Office 97 was the suite that worked for the average user. It established a feature plateau so stable that businesses refused to upgrade for nearly a decade. It wasn't uncommon to walk into a small law firm in 2005 and find Office 97 humming on a Windows 2000 machine—because why fix what wasn't broken?