Microsoft Windows 1.0

The first Macintosh operating system popularized the concept of graphical user interfaces when it was launched in 1984, and a year later Microsoft responded with the first version of Windows--and no GUI has been as blocky or garish since. To be fair, the first Windows wasn't so much an operating system as an add-on to MS-DOS, which meant living with design groaners like ALL-CAPITAL file names and the still-very-DOS-like graphics standard. Though more than a few people would contend that Microsoft has been playing catch-up with Apple's design sense ever since, the ugly duckling did eventually turn into a swan with Windows Vista. And, as we understand it, Windows has done kind of okay in the marketplace.