That will run on all of the above? Well... DR-DOS, probably. I know 7.03 would at least /boot/ on a Tandy 1000SL. That's an 8086, not an 8088, but I suspect it would run on an 8088 too. I've also successfully booted it on an Opteron, so I suspect it would have no issues with a Pentium 4. I've certainly run it successfully on Slot A Athlons and Pentium IIIs.
Otherwise, the OS that holds a special place in my heart is probably still OS/2 Warp, though of course it won't run on anything older than a 386, and getting it working on anything newer than a Pentium Pro is a real challenge (though possible). When I got my first "real computer" as I thought of it - a 486DX4 - it came with a broken installation of Windows 3.1 on a broken installation of MS-DOS (many files were missing, nothing worked right). The only things I had to reinstall were my DR-DOS floppies and a copy of OS/2 Warp 3.0 that I'd found at a random nearby computer shop. I installed OS/2, and then DR-DOS in another partition for my games that didn't work in OS/2 (surprisingly few, actually), and I ran that for a few years. So in a sense, I still think of that as my first "Real OS" - what with its multitasking and whizzy features, and a GUI much slicker than the Windows 3.x one. To be frank, I don't think Windows really caught up to OS/2's desktop experience until at least XP - and some of that is just me having finally gotten used to Windows' warts by then. On Unix, I still prefer a somewhat more OS/2-like environment, with drag and drop, a launchpad/panel, etc.
That box eventually got Win95 for a few weeks - out that went, and back in OS/2 went, about the time it crashed on me and cost me a full day's work on a research paper. At some point in there I started messing with Linux (and FreeBSD) and discovered KDE (great stuff, KDE 1.0 was), but that's another story. Linux and Solaris may be what I use mostly today, plus Windows for games, but OS/2 still holds a special place in my memories.
Main Box: Macbook Pro M2 Max
Alas, I'm down to emulation.