alt Hacker Newsxv is my favorite image viewer of all time. I loved how it launched immediately and made it very easy to see an image or browse a folder right from the command-line. 20 years later, computers are dramatically faster and such a fundamental task has become unbearably laggy.
30 years later and the basic functionalities of Windows 3.1's File Manager and Word 6.0's object linking and embedding still aren't doable on the web.