Have anyone gotten them to run in wine? Or is playing in a VM my only option?

I managed to get both games installed on linux mint debian edition x64 using "wine ...exe /nogui", but neither game is playable.

1 freezes on the SSI intro video after asking about changing resolution, and 2 freezes with an error popup at the main menu screen.

I have no problems running imperialism 1 on my machine.
I'm running LM17 and using wine 1.6.2-0ubuntu4. My screen resolution automatically changes to 640x480. I haven't had to do any settings tweeking for wine. I'm by no means a wine or mint expert.

Thank you for your reply VanBantam! I tried starting Imperialism 1 on LMDE with 3.11-2 on x64 tonight and it worked fine. There is no upscaling happening though, but that shouldn't come as a surprise.

Imperialism 2 starts with the intro video playing in a peculiar way to the side of the center of the screen, and then it nags me constantly with the same error popup from the game or wine about:
ASSERTION
D:\Episolon\win_cd.cpp @407
_winCdPlay
[ OK ]

The game can be started but the error keeps coming up on top of the full screened game and has to be dismissed with OK every time which makes the game practicallly unplayable.

Same problem on my Mac when I try to port it with Wine. Seems to be a problem with Wine.

Lower the music volume to zero.

I read that error was linked to the absence of a detected CD-ROM drive. I personally got around it by mounting a random iso and then adding that drive to Wine.

I am experiencing another issue though, in that the screen is desesperately white. Even more infuriating when I switch out of the game, while resizing the screen to display my desktop, I can catch a glimpse of the opening screen. It's there, just hidding! Grumpf!

[That was some thread necro - just got the game and got overexcited I guess!]

Wow. Thanks for the CDROM idea - it worked perfectly.

As for the other issue I don't know how to help you but if it does help in any way, I'll tell you my configuration that does work:
My computer is an Asus laptop UX302L, it has an i7 CPU with integrated graphics and an NVidia dedicated card.
I'm using Kubuntu 16.10 x64, KDE plasma: 5.7.5, Qt version 5.6.1, kernel version 4.8.0-59-generic

I use the nouveau drivers (not the nvidia blob).

Wine version is 1.8.

Wine settings for Imperialism II are:
- Windows XP
- D: drive pointing to the game directory and type set as CDROM (thanks again!)
- Z: drive pointing to /