Interestingly, if you have access to the source, which takes some effort but is available after some paperwork, it has tools to compile specifically for greater Wine compatibility.
Besides that, I run Excel 2003, because nothing else even comes close to the power of Excel+VBA.
I also run some old multimedia educational software, as well as a multimedia Encyclopaedia Britannica.
A really nice tool to work with timing transcripts to audio and then using them for shadowing/chorusing, called WorkAudioBook.
Some old typing tutors for Chinese.
Would LIKE to run Paint.NET like someone mentioned elsewhere.
Winamp and foobar2000, two media players that are simply unbeaten by anything on Linux, and believe me I've tried everything. Although at the moment I'm committed to running mpd, so they're not getting as much use now.
Also games obviously.
If I'm going to use a Windows app I'll see if it runs in WINE first before breaking out a VM, it's convenient like that.
Now that doesn't mean I don't have other issues trying to do sound in Linux, but things have been improving considerably in the last couple years. Pipewire is also pretty solid now.
Proton uses wine heavily, so there is a massive market with the steam deck using wine to run their games.
Also, some 16 bit Windows applications that probably won't even run on current Windows, like the Windows Entertainment Pack that shipped with Windows 3.1. You can pry that version of Tetris from my cold, dead hands.
Of course, I also use the version of Wine that's built into Steam for nearly every game I play.