Third-party tools include WineBottler, PlayOnMac, and Wineskin. There’s also the free Porting Kit, which makes installing classic games easy, and the commercial CrossOver Mac, which is the only application here you have to pay for. We’ll be using WineBottler for this tutorial, as it seems like the most popular option among Mac users. Additional steps (Catalina Catalina you can either update macOS or disable System Integrity Protection. Hey, as someone who has previously 'maintained' a wineskin for osu! On mac, this is pretty amazing considering that you made an entire agent program for this!

With 32-bit program support going away on the Mac with Catalina we need to start seriously figuring out how to have WINE run on these newer systems so that reasonable instructions can be provided.
Right now we can use VMs (VirtualBox, Parallels, VM Fusion) using other operating systems (Ubuntu, Red Hat, or if you can actually get it to work an older version of the MacOS) thought doing this correctly is kind of 'uhhh, how do you do that?'
But is that the best (ie easiest) solution we can come up with or is there some other method on the table we could use?

Note: I know this is an old thread, and am just posting to help anyone else who stumbles upon this thread.

First of all: Wine (just plain wine) is NOT available for Mac, so that leave you with Wineskin, WineBottler, PlayOnMac, or CrossOver.

Wineskin and WineBottler are intended for creating wrappers, which is basically converting it to a Mac application.

Wineskin gives you more customization over your wrapper.

WineBottler also comes with a system that lets you just run any exe on mac just like that.

PlayOnMac lets you download and run supported apps easily, but isn't good for just any exe.

CrossOver is paid software.

Wineskin Para Mac Catalina

If all you want to do is run exes with right-click>Open With, than install WineBottler.

Wineskin Alternative Mac Catalina

Nov 24, 2015 9:19 PM