Edited on 12-28-14 to reflect changes with CrossOver.

Warning: This is going to go deep into tl;dr territory.

I’ve heard all around the forums various questions about how to run many (Windows-only) GOG titles on Mac OS X. I’ve seen some general pointers, but there doesn’t seem to be a good overall how-to for the less technically savvy among us (read: n00bz). To that end I’ve decided to try to write up a more comprehensive how-to for playing GOG titles on the Mac. For now, I’m going to focus on how I use a combination of , [url=http://www.scummvm.org/]ScummVM, and CrossOver to do this.

What you need:

a) An Intel Mac. That means any MacBook, MacBook Pro, Mac Pro, and an Intel-based Mac mini/iMac(1).
b) A Windows/Windows emulation(2) environment. The best case scenario is that you have either access to a separate machine running Windows, or a Windows install running on your Mac via Boot Camp, Parallels, or VMWare. The worst case is that you don’t and all you have is Darwine, the Mac OS X port of WINE. Somewhere in the middle is CrossOver or CrossOver Games.

(1) The Mac you need of course depends on the game you’re trying to run. Obviously you shouldn’t try to run Painkiller on a GMA 950-eqipped MacBook or Mac mini.
(2) Yes, I know that WINE/CX are actually not emulators, but I’m using that word more out of convenience.

Method A: General Installations - for Games That Do Not Run Natively in Mac OS X

Step 1: Do your homework. Does the game run natively on Windows? Does it use DOSBox, or ScummVM? Places like Wikipedia, Moby Games, or GOG’s own are immensely useful. Courtesy of <span class="bold">Miaghstir</span>, [url=http://www.dosbox.com/wiki/GOG_games_that_use_DOSBox] here is a list of GOG titles which use DOSBox (last updated in January 2010). Other useful places are the Inside Mac Games forums, and the MacHeist forums. (Disclosure: I’m a moderator on the MH forums, and I’ve posted to threads discussing the use of CrossOver Games to run GOG titles on the IMG forums.) You won’t get any sympathy from anyone here - including me - if you blindly buy any game you see without due diligence to find out if it will actually run through CrossOver/WINE or any of the other interpreter/emulation environments used.

If your game of choice is a native Windows game then you need to first hit the CodeWeavers CrossOver Compatibility Centre (C4) to see if it will run in CX. If your game isn’t listed, or if the information on it is more than several months old, then look at the WineHQ for more information. CX usually lags behind WINE by several versions, but in general, if it works in WINE, it should work in CX.

Step 2: Run the Installer. In this instance, I’m using CrossOver (version 14.0.3 as of this writing) as my Windows emulator. I’m going to assume that you’ve already downloaded and installed CX and setup a Windows XP bottle within it. You may already have one if you’ve installed another Windows app like Steam. Go to “Configure” > “Install Unsupported Software...” and follow the instructions(3). At the final step, make sure “Choose Installer File” is selected and click “Install”. The GOG installer should launch(4). To save on drive space I usually elect to not install Acrobat Reader or Foxit Reader.

(3) I generally install all of my games in the same Windows XP bottle to save on drive space. You can install your games in individual bottles if you wish; the advantage to that is that if your games need specific tweaking of Windows settings to work, they won’t interfere in the functioning of other games.
(4) You could also double-click on the .exe installer in the Finder of course, and it’ll launch CX and go straight into the GOG installer. The downside is that the install is done directly into the default bottle.

If your game runs natively in Windows, then you’re done. CX will thoughtfully populate the “Programs” menu with your game(s) - they’ll be listed in the GOG subfolder. Examples of games which work flawlessly this way are Painkiller: Black Edition and Heroes of Might and Magic 3: Gold Edition.

(If your game is a DOS title (e.g. Gabriel Knight: Sins of the Fathers), or is a SCUMM-based game (e.g. Beneath a Steel Sky), then proceed to...)

Step 3: Get the Game Data Files. Go to ~/Library/Application Support/CrossOver/Bottles - since I usually install in my Windows XP bottle, I would find my game files in /winxp/drive_c/Program Files/GOG.com/“InsertYourGameTitleHere”. The location of your game’s data folders may vary depending on how you’ve set up your Windows bottles in CX.

(If your game is a SCUMM-based game, skip to Step 5.)

Step 4: Install in Boxer. I’m going to also assume that you’ve installed and set up Boxer(5) on your Mac. Launch Boxer - this should bring up the “DOS Games” folder that it should have installed for you. Take the folder “InsertYourGameTitleHere” and drag-and-drop it on to the icon “Drop games here to install”. Boxer will then automagically copy and package your DOS game, as well as a DOSBox configuration file in a neat little .boxer ‘Gamebox’ file in the DOS Games folder. This is a file which you can launch just like a typical Mac application, with no configuration or setup needed. I suggest you pretty it up to look nice afterward. After all, you’re a Mac user: eye candy should be important to you, shouldn’t it?

(5) I choose Boxer as opposed to a raw DOSBox installation plus or [url=http://members.quicknet.nl/blankendaalr/dbgl/]DBGL because Boxer was designed from the ground up to make DOSBox game use/installation as quick and painlessly as possible for Mac users, at the cost of easy tweakability and customizability. There’s no technical reason preventing you from going this route instead of using Boxer.

Step 5: Install in ScummVM. Again I’m assuming ScummVM has been installed on your system. Fire it up and hit “Add Game”. This will bring up the standard Mac Open/Save dialog, where you can navigate to ~/Library/Application Support/CrossOver Games, which you can further navigate to find “InsertYourGameTitleHere”. Select it in the list of games available and hit “Start” to play.

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Brief FAQ:

Q: Game XYZ doesn’t work! What now?
A: Check in the game’s specific forum here on GOG for troubleshooting help. Otherwise, check your game’s listing on WineHQ or the C4 for more details. For DOS-based games, Vogons is a good place to start.

Q: Why CrossOver? It’s not free!
A: No, it’s not. But CrossOver is far easier to deal with than WINE, at least for people wanting a quick way to install their games. CX comes with a 30-day trial, so you can use it to install GOG’s games during that period. Bear in mind that CodeWeavers’ efforts go directly to maintaining and supporting WINE development, so spending the extra coin for the added support of CrossOver is worth it, IMO. I will focus on using WINE in a later post.

Q: I have a PowerPC-based Mac. What do I do?
A: Unless you have access to a Windows PC or a Windows installation running on the Mac version of VirtualPC, you’re SOL. Once you get access to your game data files, you will be able to run DOS-based and ScummVM-based games, as DOSBox, Boxer, and ScummVM all come as Universal Binaries. Sadly, no current feasible solution exists for running Windows x86 binaries on PPC.

Q: I'm having issues with joystick support for certain games (e.g. IL-2 1946) in CrossOver.
A: USB controller/joystick support continues to be one of the main issues in WINE and in CrossOver, and it seems to be a little hit or miss with certain games. The best thing to do would be to find a gamepad that has support for both Xinput and DirectInput, as many older PC games work best with DirectInput-aware devices.

This is a very good summary of all the options.
It should also be noted that some of the games have cross-platform engine remakes available, such as the Descent and Freespace games. As with DOSBox- and ScummVM-based titles you can literally just dump the OS X binaries into a PC install and start playing.
The engine remakes are typically mentioned in the game's forum (often as a sticky) so they are quite easy to find.

Good post. Rep given.
A listing of which games need what solution may be appropriate:
* GOG games that use DOSBox
... listing of ScummVM-games and Windows games may come later.

Edited on 12-28-14 to reflect changes with the JA2 open source port for OS X.

Thanks for the great feedback. In reponse to Arkose here is a followup how-to for installing GOG games which have source ports for Mac OS X. I was working on another followup using Darwine, but my tinkering with Mike Kronenberg's packaged version ended up seriously breaking Steam and my Windows XP bottle. Sigh. Now I have to reinstall Half Life, Deus Ex and Torchlight again...

Method B: Installations - for Games That Have Source Ports for OS X

Some games on GOG have had the good fortune of having their core engine open-sourced, with enterprising individuals porting what was once a Windows-only game to Mac OS X/Linux; to some extent the ports are feature-limited, or can be highly buggy/unstable. As always, Caveat Emptor.

Step 1: Do your homework. Now you'll have to suss out what games on GOG have open source ports that run on OS X. Beware, some updated OS X ports may only exist as source code which you'll have to compile yourself. Here's a short list of open source ports that I know of:

Descent 1/2: , [url=http://www.dxx-rebirth.com/]DXX-Rebirth, D2X (D2X-XL is arguably the better of these.)
Jagged Alliance 2: Jagged Alliance 2 - (compiled binaries by [url=https://bitbucket.org/gennady]gennady)
Duke Nukem 3D: (compiled binaries by [url=http://www.spam-filter.de/osx/eduke32_on_os_x]spam-filter.de)
Rise of the Triad: ROTT OS X
Freespace 2: FS2 Open
Freespace: FS2 Open (through the FreeSpace Port, an optional install for FS2 Open)

Check their associated forums for possible compatibility issues (e.g. if they break under newer versions of OS X). Some ports, like the JA2 port, may be Intel-only, or may have out of date PPC/Universal Binaries. Some may just have out-of-date Mac ports.

Step 2: Run the Installer. Use CXG or WINE to extract the installer's contents to your Mac, the general procedure is outlined in Method A.

Step 3: Install Your Game. Check the source port's respective sites/forums for installation instructions. Some may require you to install dependencies like SDL. In some cases all you need to do is simply drag and drop the data files into the same folder as the application. For others, like FS2 Open, you need to download a small Java executable which acts as an online installer.

Step 4: Install Extras (Optional). Many source ports support mods, extras, and other add-ons which enhance the game experience. D2X-XL's page has links to high-res sounds/textures and 3D models, as well as additional fan-made maps. eDuke32 supports high-res textures and 3D models from the HRP, and, if you've got the space, the FS2 Open installer has options for bonus content like the FS-FS2 port, The Babylon Project (a *very* cool Babylon 5 FS2 Mod), and others.

---------

Brief FAQ:

Q: Game XYZ doesn’t work! What now?
A: Be patient and consult the source port's associated forums. Odds are you put some files in the wrong place. Also bear in mind that depending on how the programmer did his/her work, the current port might either need, or be broken by, the latest OS release.

Q: The Mac port of game ABC isn't as fully featured/stable as the Linux/Windows version... Huh?
A: Many porting efforts are plagued by chronic underfunding, as well as a chronic lack of experienced Mac porters. Many ports are done without even any Mac testing. This is the result. Donating whatever you can to their efforts is what's really needed, or a willingness to learn to code and help them out. Other than that the only thing you can do is wait until someone picks up the Mac source and updates/fixes it.

Q: I've heard that you can use the data files from some games to convert the demos of their official Mac ports into full Mac versions of the game! Is this true?
A: According to the folks at InsanelyMac (the lovely people who brought us the OSX86 project), yes, you can. UT2K4 and Prey have both, apparently worked this way (the linked thread has the instructions). I myself can't vouch for this as I tried to convert my disk-bound PC copy of Prey to the Mac version, and it didn't quite work.

Q: I know of some new ports that have cropped up...
A: Feel free to post them here, and I'll add them to this post, complete with attribution!

Addendum: There is a far easier way to extract data files for GOG games that have Mac open source ports and for DOSBox-based games: a utility called Universal Extractor which essentially extracts all of the files in a .exe installer, and dumps them into any folder you choose, even locations outside of a CXG bottle/Wineskin wrapper, like your Desktop or Home folder. All you have to do is open the installer from within UniExtract.exe -- it couldn't be simpler.

This is all fantastic and it works wonderfully for me. I was wondering how to install patches for games this way (i.e. hi-res patch for Fallout).

Edited on 28-12-14 with additional troubleshooting tips for Wineskin.

First, my apologies for resurrecting a dead thread. I promise this won’t be as tl;dr-ish as the last ones.

For a while, there was one mechanism by which I’d recommend playing GOG titles, or in the case of some titles, extracting their data files for use with open-source ports or DOSBox/ScummVM. That was CrossOver. There were alternatives like WineBottler, but I often found them hard to configure or extremely problematic. or [url=http://barrelapp.co.uk/]Barrel are other potential options.

Thanks to users like paulthetall and mistermumbles, and NoanRand however, I discovered a new, totally free way to do so without the use of CrossOver: Wineskin. It’s a highly modular distribution of Wine for Mac OS X, it’s biggest strength being that it can actually independently use multiple versions of WINE for maximum compatibility...handy for when a game gets broken in a new WINE or CX release. As always, the usual disclaimers apply: this is not officially supported by GOG, and if you didn’t do your homework before buying any given title, it’s not our responsibility if it doesn’t work.

Method C: Windows games with no Mac ports through Wineskin

Step 1: Download and install Wineskin, as per its instructions. Using Wineskin Winery, be sure to WINE engine(s) to use with it - as of this writing, there are Wineskin engines built around both WINE itself (the development 1.7.x and stable 1.6.x branches) and CrossOver (CX). Some engines have the suffix "NoXinput2" - these are specific WINE builds which do not have Xinput enabled, and [url=http://portingteam.com/topic/7728-what-does-no-xinput2-mean/]might be useful if you're experiencing control issues with certain games. Engines with "NoFlicker" have modifications to get around flicker/graphics corruption issues in some games. Engines with "D3Dboost" have the experimental CSMT patches added to boost graphics performance.

You can view the release notes in the "Add Engine" window, which comes up when you click the "+" button in the Wineskin Winery. This and info from the AppDB should be useful in deciding which WINE engine to use for your game.


Step 2: Select the Engine of your choice that you've downloaded, and create a wrapper. Hit "Create New Blank Wrapper" to create a what will essentially be a self-contained standalone instance of WINE for use with your game. Provide an appropriate name for your wrapper; pay attention to what characters you're not allowed to use in your wrapper's name.

Once you've created a wrapper, an installer will ask to attempt to download and install Mono and/or Gecko packages - you should confirm it only if you know that your game needs Mono/.NET or mshtml to run. Otherwise, you should cancel the installation as they take up a large amount of drive space. After they're done, hit "View Wrapper in Finder" to take you straight to your finished wrapper. By default, wrappers live in ~/Applications/Wineskin.


Step 3: Launch your new wrapper to run your game installer. That will immediately launch the built-in Wineskin.app (the application which acts as your direct interface to the inner workings of WINE for your wrapper). Hit "Install Software" and navigate to your downloaded game's installer .exe file.


Step 4: Configure/Tweak WINE. Some games, like Sacrifice, need special WINE options turned on or off. In Wineskin.app (which you can also access through right-clicking and selecting "Show Package Contents"), hit "Screen Options". Disabling "Decorate Windows" is equivalent to disabling "Allow Window Manager to Decorate the Windows" and "Allow Window Manager to Control the Windows" in winecfg.
- If a game needs a Virtual Desktop, hit "Override" under "Override Wine control of Screen Settings" and change the Override Settings from "Normal Windows" to "Virtual Desktop at (select your resolution)".
- Some games (like in my experience, Age of Wonders 2 and AoW: Shadow Magic) require "Auto Detect CPU info for Direct3D" to be disabled to run. Notably, this option doesn't exist in CrossOver.
- "Use Mac Driver instead of X11" can be enabled here; this may/may not clear up performance or graphical bugs in the game.
- "Use Direct3D Boost (If available)" is for engines that have the D3DBoost label, or for CX engines > 12.0.0.


Step 5: Customize your wrapper. Hit the "Advanced" button. This gets into the nitty-gritty of WINE. Here you can specify the .exe launched when you launch the wrapper, as well as other esoterica like version number and menubar name. I like to change the version number to reflect mods or fan patches I've applied. For custom icons, any size graphic converted to .icns format will do, but 512x512 images are recommended.
- The "Tools" tab in "Advanced" gets you to important WINE configuration tools like regedit, winecfg, and Winetricks. You can also change the engine here.
- The "Options" tab gets to specific settings needed for specific games; for example, "Disable all CPUs except 1" for Dark Engine games (SS2, Thief, Thief 2).
- A highly helpful feature here is the Test Run button, which works like it says - handy for quickly testing out configuration changes for games.

Step 6: Make a .app for your game's setup .exe. Many GOG and classic games come with an associated setup.exe to allow user control over highly specific game options, and are necessary to get the right set of configuration options to work in WINE. To make access to these setup .exe apps easier, go to the Wineskin.app file in your wrapper, hit the "Advanced" button, select "Tools", and select Custom EXE Creator. This will generate a .app file for the setup .exe app for your game.
- Here you can navigate to your game's setup .exe app, set a name for the corresponding .app and configure other options. Once finished, the corresponding .app lives inside your wrapper, in the same place where Wineskin.app resides.

FAQ:

Q: Wineskin doesn't work/doesn't work properly...
A: Apart from an Intel Mac, Wineskin requires 10.6+. If your Wineskin wrappers aren't starting up correctly, try doing a reboot, or log out/log in.

Q: My game didn’t work. And yes, I did my research. You and others even said yourselves that this would work in CrossOver or WINE!
A: Make sure you try disabling things like Decorate Windows and Auto Detect GPU info for Direct3D, or enabling a Virtual Desktop in Screen Options. Setting ddr=gdi in Winetricks (Wineskin.app > Advanced > Tools) may help too. Other registry edits may be required as well. Your game may also need additional dependencies which you can also install in Winetricks, such as d3d9_36. Look up the game's entry on the WINEhq AppDB to see what your game might need.

Q: I see all of these choices for WINE engines in Wineskin Winery! Which one should I choose?
A: My general policy is to start trying the more recent engines first, then selecting older builds if they don't work. Some games work best with the legacy 1.3.x series like Soul Reaver and Soul Reaver 2, while some games work best with the stable 1.6 series. Others work best with the more recent fixes introduced in the unstable 1.7.x branch. Be prepared to take some time to test for the version of WINE which works best with your game. In my general experience, I've gotten the best results with the 1.5.31X engine.

If you're experiencing mouse control issues, try using an engine with the NoXinput2 suffix, and for graphics flickering/corruption issues, try an engine with the NoFlicker suffix.


Q: I upgraded to Lion (or any version of OS X above 10.7) and I'm seeing screen corruption and artifacts!
A: Changes in the underpinnings of the OS introduced in 10.7 may break full screen rendering for many games in WINE. If setting ddr=gdi in wintricks doesn't work, try enabling a virtual desktop for the game in the highest comfortable resolution possible. Otherwise, be prepared to have a separate partition with a working 10.6 install handy, if possible. You can also try the NoFlicker engines, as well as some special custom-made engines also.

Q: Where does Wineskin store its wrappers? Where can I find my windows files?
A: Go to ~/Applications/Wineskin. Your wrappers (and any installed Windows apps therein) will be found there.

Q: Are there premade wrappers for games on GOG?
A: paulthetall has an extensive repository for information on using Wineskin, as well as CrossOver, for Windows game compatibility here: http://www.paulthetall.com/page8/page39/page39.html - he also provides premade Wineskin wrappers which you can download for use with your GOG installers. Doh123 (the person behind Wineskin) has also made an older wrapper for use with Neverwinter Nights here: http://nwn.bioware.com/forums/viewtopic.html?topic=725075&amp;forum=71 (As a disclaimer, I’ve tried it, and it doesn’t seem to work for me.)

Edited 4/25/12 with info on Shogo and Fallout 2.

This additional post is (a) a compilation of the GOGmixes that will help track prospective GOG customers in finding games that will run on Mac OS X either through Wineskin/CrossOver Games or Boxer/DOSBox, and (b) titles that I have confirmed will not work on OS X through CrossOver Games.

Mac-Friendly/Open Source GOG Games - my own personal mix which lists GOG games that I've personally tested on my GMA950 MacBook and my Radeon Mobility X1600 MacBook Pro, either running through F/OSS ports or through CrossOver Games. This is the best one...but I'm not biased at all. :P

GOG games on a Mac... and how! - NoanRand's own GOGmix of GOG titles on the Mac, with several contributions culled from my own GOGmix.

GOG games that work on Linux - Paldepind's own GOGmix tracking games which work on Linux through WINE. A great place to check for compatibility with CrossOver.

GOG Games using DOSBox - one of the most useful GOGmixes out there; if it works in DOSBox, it'll work on OS X through Boxer.


GOG Titles Personally confirmed to NOT WORK in CrossOver/Wineskin

1) Fallout/Fallout 2: Do not believe anyone who tells you that this game works. For a while, these games have suffered from a debilitating bug that slows the mouse cursor and the game itself to the point of total unplayability. Fixes reported to work in the past don't seem to work anymore, at least, not since CrossOver 8.x. I've heard some people here claim that it works well, but I strongly believe that they simply haven't played the game past the menu screen to confirm that it works properly. (Fixed: This game now works perfectly on CX11 and on WIneskin with WINE 1.4.)

2) Descent 3 + Descent 3: Mercenary: Suffers from some substantial graphical bugs which I believe stem from issues endemic to WINE itself. A fix is still in the works.

3) Shogo - Mobile Armour Division: Suffers from substantial stability and graphical issues. (Fixed: This game now works perfectly (as does its sister game, Blood 2) on CXG 10.3 and CX11)

Hi
with the arrival of the new Intel HD Graphics 3000 some people might wonder how well this works, since intel has a bad rep. and the nVidia 320M is considered the better card.

I made up a list of my games, around 200 and growing, that give you some regularly (as necessary) updated real world performance data on specific games on OS X and Win 7 and CrossOverGames compatibility.

I am Currently working on this so it will take some time to complete.

you can find it here:
https://spreadsheets.google.com/spreadsheet/ccc?key=0AuaYHyNVvh4wdEhlNGdrZ3dLSXJkNm9Za1dKOHdGU0E&amp;hl=de&amp;pli=1#gid=1

I hope this list will help some people.

Cheers :)

does the above post seem like spam to anyone? or is it just me?

Edit: The post has since been deleted. I wasn't trying to suggest dyscode's post was spammy.

the above posts about "free mac games" and "mac disk recovery" (EDIT: if someone is confused, offending posts now deleted by TET) are probably spam and frankly I don't even want to click the links in case they are malware traps, but because I don't want to click them it is kind of hard to verify what they are :/ but nonetheless I would say they would probably qualify as spam

I reported them - GOG can decide what they are :/

Thanks for cleaning up this thread. Apologies for the bump, but WINE 1.4 and CX11 have been out for a little while now, and many games that were previously unplayable like Fallout 1/2 and Shogo: MAD now work great. I've updated one of my other posts up to.

Fallout 1 & 2 worked before if you installed them in Win98 bottles.

They may have worked before in CXG 10.x but I hadn't tried in a while...I tried pretty much every trick in the book, from fiddling around with sfall to installing them in a win98 bottle and everything in between, but I still had problems with extremely sluggish gameplay and mouse movement. In any case, thanks for letting me know!

yay! i was wondering if this had changed. now i can add fall out 1 and 2 to the long list of gog games i can play, but haven't got round to yet...