I prefer to buy my movies from Apple’s iTunes Store. They are instantly available across all my Apple devices and allows me to get high quality versions without having to deal with the Blu-ray “bag of hurt”.

However, I don’t like the idea of movies that I have purchased being removed from my library or being unplayable for arbitrary reasons. I also like being able to use Plex, so I also need the DRM removed for that to work.

To solve these problems, I remove the FairPlay DRM from the movies using a tool called Requiem. Requiem works great, is fast, and is free - but Apple patched against Requiem some time ago. However, it still works fine on a fresh install of Lion running iTunes 10.5.1. Virtualization to the rescue!

I first tried running Lion in a trial version of VMware Fusion as that had out of the box support for virtualizing Mac OS X, but ultimately didn’t feel it was worth an $80 Fusion license for this when my usual virtualization solution (VirtualBox) could probably do the trick just fine. Indeed it could, but I ran into a few hiccups along the way. My solutions are documented below in case it helps anyone else.

I copied the VMDK image over to a new VirtualBox VM, which resulted in a black screen when booting. This was resolved by switching the chipset under “System” from ICH9 to PIIX3. After that, the machine refused to boot past ‘root device uuid is xxxxx-xxxx-xxxx’. Turns out, Lion won’t boot on Macs with Intel Haswell CPUs, so I had to fake the CPU in VirtualBox using the following command:

VBoxManage modifyvm <vmname> --cpuidset 00000001 000006fb 00000800 80000209 078bfbff

After that, Lion booted up fine and I could go back to removing that pesky Fairplay DRM.

Update 2015-02-10: Turns Out™, 1080 videos didn’t come along until iTunes 10.6, so I found on old dmg installer of that and upgraded iTunes. Then I had to go into iTunes’s settings (Store section) and make sure it downloaded HD content in 1080p instead of 720p. Requiem 4.1 supports both iTunes 10.6 and DRM removal of the 1080p videos.

Update 2017-02-27: So Apple seems to have closed the 1080p hole on iTunes 10.x. Even when prefer 1080p is selected, and with no other changes, it will only download 720p. Better than nothing, I suppose…