Wal-Mart jumped into the DRM-free pool with a big slash yesterday, as the retailer began selling high quality MP3s from major labels, at a price that undercuts iTunes.

The music industry is finally coming around to the realization that the only way to break Apple’s lock on the digital music market is to offer DRM-free music through a variety of online services. The thinking seems to be that the major labels can finally stop the iTunes juggernaut by flooding the market with affordable, high-quality, iPod compatible music. While the plan sounds good in theory, it remains to be seen whether it will actually work. If the Wal-Mart music store is any indication of things to come, the labels might want to prepare for the worst.

I was so intrigued by the possibility of buying unencrypted, cross-platform compatible music, from Wal-Mart that I decided to give the service a try. What follows is the sad and painful story of how I spent most of an afternoon trying to download one 94 cent song:

When I think about DRM-free music, I immediately assume the music is “platform independent”. That’s a geeky way of saying that it will play on an iPod, or a Zen, or a Zune, or anything else for that matter. It goes without saying that DRM-free music should also play on a Windows system, or a Mac, or a Linux box. That’s one of the many advantages of DRM-free music — users aren’t locked into one platform.

Unfortunately, Wal-Mart’s vision of DRM-free music doesn’t include platform independence — as I discovered when I attempted to enter their music store using my Mac.

We’re sorry, your operating system is incompatible. To provide the best download experience, we can no longer support Windows 98, ME or NT. Please visit again after you upgrade to Windows 2000 or XP. Visit our Help section for complete system requirements information.

Hmmm. No mention of Mac OS X — for some reason they automatically assume I’m using Windows ME. But then again, there’s no mention of Windows Vista either. Wal-Mart’s web development team clearly needs to get out more.

While I’m was not happy about the situation, I was prepared to deal with it. I happen to have a Windows system that I keep plugged in for just such occasions. Not a virtual machine, mind you. A real live Dell.

So, I login to my Dell, fire-up Firefox and head over to the Wal-Mart music store. Only to be greeted by this message:

We notice you’re not using Internet Explorer. Other browsers may be able to access our original Music Downloads store which has fewer user features than our latest version but offers the same music. We will be making enhancements to our updated version in the future to support the Firefox browser. If you want to take advantage of all of the features in our updated design now, please get the latest version of Internet Explorer.

At this point I begin to wonder what year it is. Wal-Mart’s music store doesn’t support Mac and it discourages the use of Firefox. I’m beginning to wonder if I’ve somehow time travelled into the past and landed in era when web developers actually believed ActiveX had a future.

Finally, I do the unthinkable. I start Internet Explore. I really can’t remember how long it’s been since I used Internet Explorer, but apparently it’s Wal-Mart’s preferred tool for delivering unencrypted MP3 files to the masses.

When I arrive at the Wal-Mart music store using the latest version of Internet Explorer, I’m promptly admitted without complaint.

Once inside I begin browsing the Wal-Mart catalog. First thing I notice, MP3s and WMAs are all mixed together. In fact, you’ll frequently see the same album listed multiple times — once as WMA and once as MP3. Sometimes albums are listed without an indication of what format they’re being sold in.

Searching is a challenge too. Search on an artist name and you’ll see exactly four albums by that artist. Want more and you have to click (at least) twice to see a full list of available albums by that artist.

It’s pretty clear that Wal-Mart doesn’t want any part of that Web 2.0 nonsense you hear so much about these days.

Eventually I give up searching for music and decide to browse by genre. I start with Rock -> Alternative. I’m happy to find that many alternative rock classics are available from Wal-Mart, including: Ted Nugent’s Greatest Hits, Frampton Comes Alive!, and Meat Loaf Bat Out Of Hell. They even have Jethro Tull. It’s like Wal-Mart has created an online alternative rock superstore.

Since this is only an experiment, I decide to download the Emo classic Do You Feel Like We Do? from Frampton Comes Alive!. That’s when I find out that the song is not sold separately. If I want the song I’ll have to download the whole Frampton Comes Alive! album, and I’m not about to do that. Not even in the name of science.

It occurs to me, as I’m sure it would to anyone in the same situation, that an MP3 of the song can probably be found on Bittorrent pretty easily. Fortunately for Wal-Mart I don’t really want the song.

At this point I’m begin to realize how much time I’ve actually wasted on this experiment. I quickly find an Elvis Costello song available in the MP3 format and add it to my shopping cart, then I start the check out process.

A pop-up warns me: “To make downloading music safe and secure we need to add a component to your computer”.

Huh? I’m downloading music from Wal-Mart, how can it not be “safe and secure”? Are they trying to tell me something about Wal-Mart’s security?

The message goes on to indicate that I need to install the Wal-Mart download manager and a Windows Security Update – despite the fact that the machine I’m using installs all updates automatically and is always current.

Security Update – Your computer needs a security upgrade from Microsoft so you can play protected files, including secure music files from Walmart.com. This update takes about 15 seconds. The update is safe for your computer and no personally-identifying information about you is transmitted during the process.

For those who might miss the subtext in this warning, it’s saying that you need to install a Microsoft DRM component so that you can download an unencrypted MP3 file from the Wal-Mart music store.

Normally this is the point where I would bail out and cut my losses. However, I’m here to review the whole process so I grudgingly agree to install the download manager and security update.

While the updates are running I’m left to read Wal-Mart’s terms of service. I note the restrictions on how I’m allowed to use the MP3 file that I am (hopefully) about to download:

You may download music to a single computer. You may then transfer music files and backup license files to up to two (2) additional personal computers. You may play music an unlimited number of times on up to three (3) personal computers. You shall be entitled to 1) burn Products solely for personal, non-commercial use up to ten (10) times and 2) export Products solely to a portable device capable of playing Windows Media â„¢ Audio (“WMA”) files such as a WMA-compliant MP3 player an unlimited number of times.

No mention of MP3 files at all. Sort of makes you wonder how much time Wal-Mart spent on this launch. It’s starting to seem like they might have thrown this together late last week.

Finally the downloads are complete, I’ve agreed to the terms of service, and it’s finally time to . . . REBOOT!

Seriously, in any other situation this would be the point where I dropped out of the process and moved on to doing something more constructive with my life. But I was doing this for the ‘Loper, so I had to press on.

I reboot, and briefly forget what I’m doing sitting in front of a Windows machine. Then it comes to me: Oh yeah, I’m downloading a 94 cent MP3 file from Wal-Mart. Same thing I’ve been doing for the last two hours.

I start Internet Explorer, head back to the Wal-Mart Music Store — find the Elvis Costello song AGAIN! — add it to my cart, and start the checkout process.

That’s when I’m informed that I need to install another Windows Update. I choose to ignore this message. That turns out to be a good call on my part.

Finally, I’m asked to create a new account. I’m not crazy about handing over my payment information to Wal-Mart, but then it is for the ‘Loper (so I use Lopy’s credit card number).

During the account creation process I’m offered the opportunity to signup for a mind boggling number of Wal-Mart mailing lists. I make sure all of the boxes are unchecked, then I notice something strange. They want to know my ‘baby’s due date’! I’m not making this up. I couldn’t possibly make this up. Wal-Mart apparently has some sort of maternity club and they want me to join. Nearly three hours of torture and it comes to this — Wal-Mart asking for my baby’s due date.

Needless to say, I don’t dignify the question with an answer.

I finish creating my account and FINALLY I’m allowed to download my 94 cent MP3 file.

After a bit of searching I figure out what fold my trusty Wal-Mart Download Manager has put my new song in, then I drag it over to my Mac — where it plays in iTunes like any other MP3 file.

To recap, my experience downloading one unencrypted mp3 file from Wal-Mart involved two computers, three web browsers, two software updates (including installing support for Windows WMA protected music), and a reboot.

Needless to say, my Wal-Mart Music experience isn’t going to lead me to cancel my eMusic subscription anytime soon.