Both might have their uses for specific applications... Have a look at the list of supported application for al of them... You probably want to try Wine on its own first, then something like PlayOnLinux and then one of the others, if your application is specifically supported... (Quite a few CrossOver developers work on Wine and they sponsor the hosting of the website, etc.) If you use anything other than plain Wine, you would need to take into account that you won't be helped if you ask on this forum. (The product's own forums should be used...) For CrossOver, a list of supported applications can be found here: http://www.codeweavers.com/compatibility/browse/name I you want to run several, potentially unsupported applications, Wine gets updated the quickest, but things occasionally stop working, etc... Gert