I was introduced to UNIX in 1993, Linux in 1995's Summmer, and have lost count how many X Windows desktops or windows managers have come and gone in 32 years.
I wasted too much time tweaking Enlightenment. I remember that was fun but I don't really remember much about actually using it.
OS/2's Workplace Shell feels like the biggest lost opportunity (and has nothing to do with UNIXy stuff). I really liked Rexx and the SOM stuff felt cleaner than what became COM in Windows.
Window Maker/AfterStep were my all time favourites in GNU/Linux world.
I used to be in the GNOME camp during its early days, even wrote a tiny article to The C/C++ User's Journal regarding Gtkmm, nowadays I rather use XFCE.
The original fvwm also holds a special place, that was the first I used in GNU/Linux, back in 1995, and I got to customise it quite a bit.
SOM was great, it also supported implementation inheritance, and had metaclasses concept as well.
I like COM as idea, I dislike how badly Microsoft keeps rebooting the developer experience, and isn't able to provide modern toolig as easy as it was from VB 6, Delphi, C++ Builder. For something that has become the central mechanism how Windows APIs are delivered.
Some underappreciated and forgotten tiling wms that are still viable today:
- ratpoison ("tmux for X11". Ultralight, great for kiosks and similar where you barely want a WM at all)
- stumpwm (ratpoison on steroids in Lisp)
- Xmonad (A bit different tiling dynamic that some prefer. I dig it despite Haskell, not because of it)
- Qtile (Very flexible and easily hackable in python yet reasonably stable and fast. You can reproduce for example the Xmonad or i3 experiences pretty easily)