IAmBored2: Please, if you actually knew anything about gaming on linux you'd know WINE has its own share of compatibility issues, regressions, let alone getting 16 bit support working since it's been disabled in the kernel. Any gamer would tell you that native support is far superior and has less problems than working with a wrapper like WINE.
WINE is for when you don't have another option, this person has an XP machine with XP era hardware, why should he bother with the issues of a compatibility layer?
If it is e.g. a GOG version he tries to play, it doesn't necessarily even work on XP anymore. Either the new GOG installer itself doesn't (necessarily) work on XP, or it contains some 3rd party fixes or tools (like nGlide etc.) that is not meant to work on XP machines.
But if it is the original retail version of an old game, possibly with some copy protection method that doesn't work right on modern Windows or Linux WINE ("Peter Jackson's King Kong" is one such game, for instance), or a game which needs e.g. a slower PC to function correctly (e.g. Mechwarrior 3 or Interstate'76), then an old XP retromachine may be the best option.
As for WINE being "the last option", I've had an opposite experience so far, as far as older Windows games are concerned. For instance, I've been playing the GOG version of Icewind Dale 2 on the following machines:
1. Windows 7 64bit (ASUS G75VW)
2. Linux Mint 19.3 XFCE (ASUS G75VW, ie. the same PC as above)
3. Linux Mint 20.1 XFCE (an old cheapo eMachines G730ZG)
4. Windows 10 Pro 64bit (my Dell work laptop, the fastest PC I have at the moment).
Guess where the game runs the best? The two Linux Mint machines, with WINE. Go figure.
In Windows 7 is works pretty well too, but IIRC it originally had some issues which I was able to get rid of either by changing the game's compatibility settings, and/or changing some of the in-game graphics settings.
In Windows 10 it was originally near unplayable due to very jerky scrolling, but using dxWnd wrapper with the game makes it playably smooth and overall ok, but still not as smooth as in those two Linux WINE machines.
I don't know whether this game (GOG version) would work also on Windows XP, but since I happen to have Windows XP installed on that eMachines PC, I guess I can try how it installs and plays there. I will update my findings later.
Anyway, for now it appears to me Linux WINE is surprisingly good for running old Windows games, as long as it is not a retail CD/DVD game with copy protections, I guess.
IAmBored2: Why are there so many people like you who have no clue how computers work and thus repeat such ignorant babble about how operating systems go out of service and how everyone needs the latest operating system (specifically a WINDOWS operating system.)
It is nice to be able to run your (older) games on the same PC and OS which you are using anyway, and not having to use a separate old retrogaming PC with an old OS in it. It saves space, takes less time etc.