I was told that this should probably be put into a public post for others to see, so here we are!
I sent a support ticket a while ago detailing a possible fix - it worked for me, it may work for you.
(I sent a ticket because I was unsure where to put this oops lol but now I've been told to stick it here.)
This was the ticket I sent:
(Though I do sometimes instead get a Wineskin box that refuses to do anything useful and doesn't go away. Rebooting completely seems to be the only fix for that. Closing or quitting in any way does nothing - the box still appears.)
Hopefully this maybe helps someone?
I sent a support ticket a while ago detailing a possible fix - it worked for me, it may work for you.
(I sent a ticket because I was unsure where to put this oops lol but now I've been told to stick it here.)
This was the ticket I sent:
I'm running the April 2016 download of the OSX Osu! bundle, and I was having the "Osu! straight up refuses to run at all ever no matter what" problem which seems to be rampant.It seems that this nearly completely fixed the problem for me. It eventually even started to run without the need for WINE.
The problem was always either:
a) XQuartz bounced on the dock for an eternity, doing nothing whatsoever, or
b) XQuartz bounced once or twice, then sat doing nothing, or
c) XQuartz bounced once or twice, the "Hi! Your client is being updated!" screen would show and then continuously disappear and reappear, as if the app was restarting again and again, or
d) As C, but not closing (static, no progress), or
e) As C, but closing and not reopening (like a crash, but no crash report), or
f) As C, but showing an "Osu! has crashed!" screen after a while instead.
---
Now, being someone who owns a Mac, but previously used Windows, I thought "I'll just try the exe in WINE, but I'll leave the Mac ver running just in case it decides to load." because that's something I've done a lot when Mac decides it doesn't even want to run Mac files, with mixed results.
I double clicked the exe, starting WINE, but realised I would rather stick it in a bundle for safekeeping, and in my sudden change of heart, I didn't close WINE before opening WINEBottler.
While preparing WINEBottler the package.... The Mac version loaded. The XQuartz logo stopped bouncing around on the dock and... Osu! actually loaded, completely normally, no "client being updated" window either (though that could've appeared in the background without me noticing).
I tested it and... It would appear that a possible fix for the Osu! app bundle not working... Is to just have WINE running in the background... Not touching Osu! at all - just there, running.
(Though I do sometimes instead get a Wineskin box that refuses to do anything useful and doesn't go away. Rebooting completely seems to be the only fix for that. Closing or quitting in any way does nothing - the box still appears.)
Hopefully this maybe helps someone?