I’m still using AutoCad from 2004, and PhotoShop v6.0.
I have a couple of games from 1995 on CD-ROM, but that’s outside the OP and they’re not running on Windows 10.
Tripler
I’m “dated,” but my software between the ears is still running MS-DOS just fine.
I miss “Talking Moose” - I had a lot of fun with that on my Macintosh. You could even program it to say whatever phrases you wanted fairly badly. I spent hours tweaking the pronunciations.
I also loved the Oscar The Grouch trash can on the Mac; when you emptied the trash Oscar would pop out and sing “Oh I… looooooooove trash!!” I read that little kids would unknowingly delete their parents’ important computer files by dragging them into the trash in order to see Oscar.
I still have my Paint Shop Pro v5.0 discs but I haven’t put them on my latest desktop because I don’t have an optical drive and haven’t been inspired to hook one up just for that. But I did/do enjoy the simplicity of it as sort of a “Enhanced Windows Paint” versus more modern art programs with the vectors and layers and all that.
I just remembered the fondness in my heart for Terragen, a program that generates realistic looking landscapes without much work. We actually had a SDMB thread about it way back c.2000 or so and I remember waiting hours for a simple 480x640 image to render but they looked so cool to me back then. I guess the program still exists for free private use and has been updated as “recently” as 2018. Hey, that’s not super recent but even back in the early 2000s, the dev was talking about slowing/ceasing development due to outside obligations.
Another vote for Wordperfect. Loved that program.
The program I still use is from 2000, and called Desktask. All it is is a display of my upcoming calendared items on my desktop. So much quicker and easier than looking at your calendar in Outlook. Two quick eye-flicks, and I can tell someone if I’m free or busy. Love this program!
… some of these sound appealing.
ACDsee here, too, same vintage. It’s still a great utility for image display. The later versions I looked at became bloated with needless bells and whistles. Sometimes older is better – this classic version is clean, simple, and highly functional.
It’s so old that I discovered it in a list of 32-bit applications that could run natively on Windows NT, back when there were relatively few 32-bit apps. Still running fine today on 64-bit Windows.
Thanks to @cytop for that video on Microsoft Bob. I had thought that Bob was an assistant sort of thing, along the lines of the stupid dancing paperclip in Office. Had no idea it was an entire environment. Who could ever have thought this was a good idea?
Bill Gates’s wife.
Anyone else remember using Banner Mania to print out banners? Designing banners was fun and one of the first software I remember using on our first home computer. I remember it fondly.
One thing I don’t remember fondly is the loud screeching of our dot matrix printer printing the banners out. Man those old printers were noisy and annoying.
In 1992 I acquired Murmurs of Earth - a CD-ROM that had the audio and images of the Voyager plaques designed by Carl Sagan et al. Disk 1 had a track for the pictures (runnable on a IBM PC with Super VGA or a Mac), while the rest of the disk 1 tracks and the disk 2 tracks were audio files.
I wonder if I still have it. I made the mistake of looking it up on eBay - Don’t do this unless you want to see how much some of these programs are currently worth.
Lol, this more than a full set of the books!
($215 for CD)
($150 for set of books)
Well, she was the marketing manager for it, not necessarily the creative thinking behind it. It must be embarrassing for the two Stanford profs whose ideas the GUI was apparently based on. Not surprisingly, I’ve read that kids loved Microsoft Bob, but adults were mostly offended by it, since it really does operate at an early grade-school level, as if most adults were severely intellectually challenged.
If anyone has a morbid curiosity about Microsoft Bob, it’s available for download here. The site also has a series of screenshots. Even the specially customized Gateway version is available. It’s nominally for Windows 3.1 so not sure what it will run on, but I might give it a try with Windows XP which I have running in a VM. I would not risk trying to install it in a real OS.
The history of the world type CDs reminds me, thinking about old stuff, that I have all the issues of National Geographic up to sometime in the late 90s on a boxed set of CDs. I didn’t make much use of it, though, and I recall being a bit disappointed with the quality of the page images. Also have an old CD set containing all the New Yorker cartoons ever published up to a roughly similar timeframe. And, moving on to the other extreme of silliness, a box set containing all the MAD magazine issues! 
And yes, I do have at least one version of the classic Microsoft Encarta. Haven’t installed it in a long time.
Golden Common LISP programming language - for an artificial intelligence computer class: It was the first time was in a “flow state” while programming. Almost scary.
Another vote for Wordperfect. I especially liked the feature where you could “find and replace” several different items at once.
Remember those half-height three-ring binders that came in slipcovers?
I’m puzzled by the past tense references to WordPerfect. I’ve used it since the mid 90’s, through numerous upgrades, and still swear by it.
Amen, Brother or Sister. That NatGeo boxed set was a huge disappointment.
Another former WordPerfect user here. (i just checked, btw, and apparently they are still around: Powerful Productivity Software for Home and Office
Anyway, my contribution is that I still have my old Beagle Bros disks and booklets.
I still use Picasa to organize my rather large collection of images because I’ve not found anything as easy to use when it comes to identifying who is in each image and I have no use for web sharing.
I’m kind of surprised no one has mentioned Quark Xpress. That was a good program. I made my living for about 10 years using it.
^^^They still make a newer version every year. I keep current in Quark, but where I work we mainly convert Quark files to InDesign. Most of the publishing houses I work with use InDesign and any legacy jobs they have in Quark they want converted to ID.
That’s quite interesting. I thought it was long gone. The weekly paper where I now work uses InDesign, but at this point I’m just a lowly proofreader, so it doesn’t concern me so much.