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Hitman III not launching past popup menu

On an external drive of my M2 Macbook Air, I installed a Windows 10 64bit bottle with Steam and some games. I changed the installation paths etc and both Steam itself and Outer Wilds run perfectly, but now I downloaded Hitman III and it doesn't work. The initial little popup menu (play, options, quit) shows up (options are clickable and work well) but once I click "play" the wine debugger pops up, as well as a window stating "The program HITMANS.exe has encountered a serious problem and needs to close. We are sorry for the inconvenience."
I've seen Hitman doesn't have the best compatibility (only 3⭐️) but it does seem to run for others at least.
Has anyone encountered the same issue and found a fix or have I overlooked something obvious?
I'm really new to crossover so there is a high likelihood of this being user error.

Thanks everyone!!

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