Some software is easy to use. The options are obvious, it's purpose is clear. It just makes sense. Microsoft Notepad for Windows XP is perhaps the best example of this. You type a key, and letters pop up on the screen. You select save, it saves. You select print, it prints. There are no ribbons, translucent panels, or funky geometric shapes anywhere to be seen.
Then there's software that's so frustrating or obtuse that it makes you want to pull your hair out. Its modes and features don't make any sense. It crashes, or doesn't work like you think it should. Apple iTunes (for the past half decade) and perhaps Microsoft Skype are good examples of this.
This slideshow is not about those programs. No, we are reserving this gallery for a handful of truly atrociously designed programs from modern computer history whose user interfaces still give me nightmares. When you're done suffering with me, I'd love to hear which programs give you nightmares in the comments.
(This story was first published on Oct. 26, 2015.)
1 Windows Media Player
When Windows XP first launched, Microsoft re-evaluated its history for making tasteful, logical user interfaces and came up with this guideline-breaking version of Windows Media Player that still haunts my dreams. With no drop-down menu, the full breadth of its functionality was obscured. It had no obvious minimize button. And in retrospect, its window shape reminds me of something my kid cut out of construction paper by accident. Microsoft Windows? Ha! Try Microsoft Oblique Portals.
I am not going to lie to you and say that I use FileMatrix—a file organizer program—or that I have ever used FileMatrix. One look at this illustrated screenshot tells me all I need to know. It's terrifying. Look at all those boxes, dialogs, tabs, options, lists, scrollbars, and who knows what else crammed in there. It's almost Lovecraftian in its horror, as if Shub-Niggurath himself rose from the depths and developed a UI to traumatize me.
After a year servicing PCs in my first post-high school job, many of which ran this program, I am now convinced that one of the nine circles of the fiery underworld is populated entirely by MS-DOS PCs running WordPerfect. This word processing package shipped with hundreds of features, all of which were accessible only through arcane, arbitrary key combinations. I don't care if your program doesn't have a GUI or use a mouse, making people press Shift-F7 then 2 to print a file (really, this is not a joke) is obscene.
4 Microsoft BOB
Microsoft BOB was a comfortable prison. It made you never want to leave your "house" and try something new on your PC. Mostly because you couldn't, or it was too hard to figure out how to do so. That's because every program it would let you easily run was represented on screen by a user-friendly illustration (i.e. clicking on a stack of letters to check your email). That meant every other thing on earth you could possibly do with your PC was left out. So it was easy to use—by virtue of it being difficult to do anything at all.
5 Logic Ultrabeat
When I'm not writing pithy stories, I like to dabble in music. And that invariably leads me to a world of horrible music software interfaces. Some are skeuomorphic to an insane degree (i.e. manipulating illustrations of patch plugs in Propellerhead Reason), while some are incomprehensibly knobby and geometrical like the Ultrabeat plugin for Apple Logic seen here. It's as if someone hosted a software knobmaking contest and invited only musicians to attend. The prize was a woodgrained mousepad, by the way.
6 Dwarf Fortress
Somewhere in the back of their minds, every PC gamer has a list of cool-sounding games they want to play but they never get around to for some reason. Number one on that list for me is Dwarf Fortress, an insanely detailed world simulation game for Windows that utilizes an ASCII text interface. I have installed it seven times over the years, and I still can't figure out how to play it. But everybody says it's awesome! So I feel deficient in some way. Perhaps it's time to add an entry for this problem in the Diagnostic and Statistical Manual of Mental Disorders (DSM). I'll call it: Fortrexia Nervosa.
7 Lycos Sonique
In the late 1990s, many app developers flirted with breaking interface design conventions, as we have previously seen with Windows Media Player. One of the worst offenders was Lycos Sonique (also a media player), which made playing MP3s as simple as piloting an alien spaceship. Which is to say, not very. Thank goodness this trend has passed, and I can finally get some sleep.