
Writers look fondly upon the tools we use. They recall their favorite typewriters even as the tide of technology pushes them into word processing. When I started to write, the world had already entered the word processing era. The earliest word processor I used was AppleWorks. Then, through high school, I used WordPerfect. In the decades since, I have tried out countless word processors and text editors, many of which I have written about here. But like those writers from the typewriter age, who cast a fond eye back on their Royals and Smith Coronas and Underwoods, my favorite word process was and is Microsoft Word for DOS 5.5.
I’ve made reference to this word processor in a dozen posts here, but I have never really delved into my reasons for why Word for DOS 5.5. remains my favorite. To understand why, you first have to understand my theory of word processors: a good word processor should do 3 things really well:
- It should separate the interface from the presentation layer. That is, how it appears on the screen should not be tied to how it appears on paper. Scrivener is a good example of this, where you “compile” manscripts from a source text.
- It should eliminate distractions and allow a writer to focus on writing. WYSIWYG seemed like a cool idea at first, but I think it has become too much of a distraction. When writers wrote on typewriters, they weren’t distracted by fonts and formatting. The very limited formatting that could be done on a typewriter was something in its favor.
- It should keep things simple.
Microsoft Word for DOS managed to meet all three of these requirements.

Through most of college, I used Microsoft Word for DOS 5.5. It was the first word processor I bought with my own money. I used it to write the first stories I ever wrote with the intention of submitting them for publication. I used to to write letters to friends and family (these were the days before email and the Internet). I used it to write papers, and I used it to type up my notes from classes, and print them in a way that made it easy for me to study.
I never spent much time dealing with formatting or fonts. I wrote and I printed. Word’s feature set was fairly robust, but most of it I didn’t need. There was not constant stream of updates to download. The interface was constant, reliable, and as far as I can recall, bug-free. The latter was perhaps a result of the application’s overall simplicity.
Word for DOS ultimately had one major drawback: its file format. I still have most of the files I wrote in Word for DOS 5.5., but they can’t be opened cleanly in modern versions of Microsoft Word. The text can be extracted, but only with some effort. I put in that effort and now my old Word files exist in plain text format.
I’ll admit that nostalgia for simpler software probably plays a part in my looking back on Word for DOS through rose-colored lenses. But that is no different than Isaac Asimov looking back longingly at his Underwood No. 5, or Ray Bradbury turning a ruminative eye back on the coin-operated typewriters he first used in the Los Angeles Public Library.
These days, I do all of my writing in Obsidian, which is not a word processor but rather a text editor. Obsidian is highly customizable and every now and then, I toy with the idea of creating a Word for DOS 5.5. theme that will allow me to feel as if I am writing once again using my old favorite. I hesitate only because I have learned that is a kind of distraction itself: creating a theme when I could be spending my time, you know, actually writing.
Written on May 7, 2022.
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A great, succinct summary of what we really need in a WP — and why many of us are nostalgic for lost tools. I still think fondly of XyWrite, which was a superb word processor for DOS back in the day. Then after switching to Mac, I wrote my book on the old Nisus Writer for pre-System X Macs.
These 2 applications weren’t just congenial to use — they actively shaped my habits in good ways.
Nowadays I use Scrivener for writing and Obsidian for notes, research, outlining — all the writing before the official Writing starts. And I completely agree with you about the trap of tweaking and perfecting. Software makes it all too easy to sharpen the pencil for hours instead of writing anything with it.
My first word processor was Scripsit on Tandy Model III. It was loaded from a cassette player and then saved back to the player. Tandy was connected to a typewriter via an RS232 interface (we traded IBM Selectric II for that). Paid $600 to have a 5 1/4 floppy drive installed in Tandy – that was really a big step forward – much quicker and secure save. Moved on to Wordstar in CPM with dot commands and continued to use RS232 to printer. That was on a Kaypro “portable” computer. Wordstar was really quite clean. Wordstar was ported to DOS, as I recall, and I used that for quite some time. I currently use Wordperfect because I like the way it collapses outlines and text.
I am moving to Obsidian for PKM (I’m migrating from Evernote with approx 15,000 entries). I use Notepad++ to do a lot of the writing because I normally have a number of tabs open and move back and forth with Markdown.
Donjones3008, I am familiar with Scripsit mainly through Isaac Asimov, whose used that word processor for his writing when he got started with a word processing in the 1980s. As he described, he had it setup for him the way he liked it, and then never changed it, and just used it as-is.