If there is one application on the Mac the mere mention of which brings tears of laughter to the eyes of the community, it is Windows Media Player. Despite its name, this application has very little Playing abilities and even less Media-related punch. While I am sure that Windows Media Player on a Windows machine is a relatively decent piece of software (at least I hope), I can only say that its Mac counterpart is going to great lengths to prove to million of users that Microsoft and the video world will never understand each other.

Luckily for me, and despite my routinely working with Windows-based customers, almost all of the files I receive are QuickTime compatible — mostly .mov but also some more esoteric codec/wrapper combinations that I am always surprised QuickTime handles so smoothly. This being said, I bumped last week into a Windows Media file I needed to open: it had been sent to me by a customer hoping to give me an idea of a specific look they were hoping to get for their next run of ads.

No matter what I did, though, Windows Media kept telling me that “An error occurred.” (Nice!) or that “The URL could not be found” (which, given I was trying to open a file locally had me wondering whether I had lost my sanity). I know Windows Media Player 9 for Mac does not handle all the fancy DRM the latest version of the Windows software introduced but, as the file was a couple years old already, it didn’t seem like it would be protected in such a way.

Having test machines is one luxury I never appreciated so much until yesterday. I re-installed everything Microsoft I could think of on it — from Internet Explorer to Windows Media Player —, restarted, tweaked settings to no end but also to no avail. It was three in the morning and my dark circles were threatening to reach the point where they’re beyond any chemical help when I, almost by accident, stumbled onto the site of a small music festival, offering files for download.

At the bottom of the page, a footnote stated that, due to a bug in the Mac version of Windows Media Player, it was necessary to have Classic installed to view the files. Uh?! With a shaking hand, and being by now resigned to spending my night staring at splash screens, I proceeded to install Classic onto my test machine, something I hadn’t done in about 4 years — hats off, by the way, to the people who designed the latest Classic installer, it’s a dream to use.

A little tinkering (namely restarting, creating a fresh account and allowing Internet Explorer to set itself as the default browser) solved my problem. A last double-click on the movie file opened Windows Media Player, then opened Internet Explorer. The blinkety blinkety show thrown by my routing gear seemed to indicate that something was being downloaded indeed. Then, the movie started playing, as if nothing had happened.

Had Classic been launched? Nope! I kept a close watch on a couple indicators and can confirm good old TrueBlue hadn’t been called. However, it looks like Windows Media Player 9 for Mac OS X (a recent application, might I add), expects to find something, be it a library or a file, that belongs to Mac OS 9 on the drive and fails if it doesn’t.

I’m sure it’s mentioned somewhere in a technote but, despite my efforts, I couldn’t find it. If this little tip can help anyone around squeeze a few pictures out of our beloved Windows Media Player, I’d be glad!