Ok, here's an updated table of results. I have added results for Ubuntu 8.10 native, and X.org versions for all OSs. OS / Method / Wine Version / X.org Version/ Outcome: OS X Leopard / Native / Various / 1.4.2-apple41 / Black screen or freeze Ubuntu 9.04 / Native / 1.0.1 / 1.6.0 / Black screen or freeze Ubuntu 8.10 / Native / 1.0.1 / 1.5.2 / Black screen or freeze Ubuntu 8.10 / Parallels / 1.0.1 / 1.5.2 / Fully working Ubuntu 9.04 / Parallels / 1.0.1 / 1.6.0 / Fully working As you can see, Wine version and X.org version are the same in the native and virtual versions of each OS. The only thing that changes each time is the method (native vs. Parallels) and hence, presumably, the driver being used for the video card.