If you could bring back classic Mac OS software, what would it be?

Not quite the same. Today’s macOS is a kludge of useless bloat. I prefer the cleaner OS 9 and below interface.
Yep, 9.3 with upgraded USB and much larger Disk Partitions would be fabulous, no IOS crappiness.

Buggage free 9.1.1 re-release for older machines that top out at 9.1 would be quite nice as well.
 
Personally I like Aldus SuperPaint better than MacPaint.

And they did try to bring back HyperCard with SuperCard, but it sadly went nowhere.
I too preferred SuperPaint. SuperCard was a separate product to HyperCard, and lasted quite a long time -- the last version was 32-bit Intel, so lasted until 2019 as runnable software. It then stayed in support until 2024 when Scott passed away and the site was taken down.
I never ended up spending much time with SuperCard because it didn't have a free runtime in the early days, and then later on, everything it did could be done in a web browser in a cross-platform manner.

Oh, and then there's GraphicConverter by Thornston Lemke -- slightly more recent than SuperPaint, as it was released in 1992, but unlike SuperPaint, it's still being actively developed today (currently on version 12). And as a bonus, Thornston has made all the "classic" versions freely available - you can still download them from lemkesoft.de today, and he's provided registration codes for them.

I find it awesome that he's been able to keep a shareware product going from 1992 right through 2026 and counting.
 
Oh, and then there's GraphicConverter by Thornston Lemke -- slightly more recent than SuperPaint, as it was released in 1992, but unlike SuperPaint, it's still being actively developed today (currently on version 12). And as a bonus, Thornston has made all the "classic" versions freely available - you can still download them from lemkesoft.de today, and he's provided registration codes for them.

I find it awesome that he's been able to keep a shareware product going from 1992 right through 2026 and counting.
I still use GraphicConverter, it still runs well on my M1 MAX.
 
There's an audio editor called SoundMaker that has enough interesting quirks that I keep returning to it. I wish I had the source code for it, or even just the SDK to write plug-ins. There's just something about the interface.

Word 5.1 was also pretty great.
 
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