How-To: Play WMV files in iTunes [OSX]
Update 10/17: Window users can read our tutorial here: How-To: Convert WMV to MOV for playback in iTunes [Windows].
This tutorial is geared towards OSX users. Unfortunately, Windows users will have to sit tight for awhile until we find an alternative method. Hat tip to Adam from the Aqua-soft boards for providing this tutorial to pass on to UNEASY readers.
Completing this tutorial will allow OSX users the ability to playback .WMV / .ASF (Windows Media video files) from within iTunes. Quit wasting space on ~40MB .MOV files when you can have 11 – 12MB .WMV versions. On with crux of Adam’s tutorial:
1) First, you’ll need videos. Might I interest you in UNEASY’s educational posts here (300K streams) and here (700K streams)?
2) Spend $10US to buy a nifty little plugin called Flip4Mac. Flip4Mac allows Quicktime (and therefore, all Apple apps using Quicktime) to play back WMV files, including those encoded with the WMV3 codec, which cannot be played on most media players for the OSX. Flip4Mac is available as a limited – half the video – demo if you don’t feel like shelling out the cash.
3) Once you have downloaded and installed Flip4Mac, quit and restart iTunes to restart the Quicktime components.
4) You’re almost done. Now you’d think all there was left to do is to drag your WMV files into your iTunes library and start watching away, right? Wrong. Even though Quicktime (and thus, iTunes) now have the ability to play WMV files, iTunes is a picky bastard and refuses to import anything with a nasty Microsoft extension. Therefore, the extension “.wmv” that’s at the end of all your videos needs to be changed to “.mov”. This sounds like a daunting task, and it can be if you do it by hand. But if you use an app such as Automator or FileWrangler, renaming these extensions can literally be done in seconds. It should be noted that even though your videos have had their extensions renamed, they are all still WMV files; only now they’re disguised as .MOV’s. A bit funny, eh?

Click for a larger preview. That’s a Gorillaz .WMV file playing in iTunes 5 on OSX Tiger.
5) Now that all your videos end in “.mov”, iTunes is more than happy to admit them into it’s library. Importing videos can be done by selecting “File>Import…”, or by simply dragging the files from a Finder window into an iTunes playlist or the Library itself. Better yet, once all your videos have been imported, the metadata in them can be edited, just as if you were editing the ID3 tags [...]
Note: Be aware that there are a few minor bugs depending on your hardware configuration. Adam reported that his 800Mhz G3 640MB machine suffered from a brief 1 – 2 second delay after clicking play. There’s also a glitch if you manually pause and restart the video. The audio and video tracks will be out of sync. It’s a disadvantage of making a less superior .WMV file play as though it were a .MOV file.
Update: Adam reports that the sync issues are resolved by running the latest Flip4Mac release.
