Older iTunes Installs on Latests OS X’s

As iTunes is an Apple-written application and has many low and system-level hooks and API calls, it would be difficult to maintain more than one installed version.

iTunes 12 is probably the oldest version you could install on High Sierra.

If you really prefer the older version(s), consider creating a Mac OS X virtual machine and playing your media from inside that.

You might also wish to consider an alternative media player, such as VLC, Vox, or Amarok.


The program Retroactive is able to install iTunes (and other programs) on non-compatible Macs, namely Catalina, Big Sur, and Monterey.

I do not believe that it would meet your use case, as you are trying to install an older iTunes on a computer that already has iTunes