Who’s going to buy $1.29 iTunes songs? No one.

So it’s officially the month of May. I wonder what’ll happen later this month when Apple begins offering those overpriced, oversized DRM-free music tracks in the iTunes Store and no one buys them?

What, surprised to see me predicting failure for Apple? After all, it’s not often that the company has blown it in the past decade, and they’ve largely been able to gloss over the few goofs that they have made (iPod+Musicmatch for Windows, the Mac mini, etc.) by changing directions before too long (or in the latter case by making the sales numbers private so no one would catch on). But if the upcoming $1.29-per-song, DRM-free, 256 kbps bitrate offerings in iTunes don’t gain any traction (and they won’t), then I don’t think we can view it as failure on Apple’s part at all.

In fact, I think it’s exactly what Apple is hoping for.

Look, Apple’s not stupid. Steve Jobs and company have to be fully aware that all the noise that’s been made over the past five years about both the DRM and the 128 kbps bitrate of the songs available in the iTunes Store has largely been made by a rather small group of users. Passionate they are. Large in number they’re not. The sales they’ll account for won’t amount to much more than a rounding error.

Seriously, who’s going to be buying these $1.29 tracks? Let’s take a look at the various possible candidates…

The folks who are still “acquiring” music for free via pirate networks. You’re going to get thieves to stop being thieves by asking them to pay thirty percent more? Not a chance.

Those who dislike the principle behind iTunes DRM even though they know they’ll never run afoul of it. Methinks these folks will stick to their philosophical guns and manage to find something they don’t approve of when it comes to Apple’s DRM-free music.

The self-proclaimed audiophiles who’ve convinced themselves that 128 kbps AAC sounds like a phonograph. The ones who refer to 256 kbps AAC as sounding “closer” to CD-quality? Expect them to stick to buying physical CDs, ripping them into the super-bloated Apple Lossless format, and continue to brag about the fact that only they can hear the difference.

Users of non-iPods. No one said your Zune is suddenly going to sync with iTunes. Getting DRM-free iTunes tracks onto a non-iPod is going to be anything but a walk in the park. There will certainly be some geeks who will buy a few songs from the iTunes Store just so they can say they’ve managed to put them on their iRiver, but don’t expect them to make a long-term habit out of it.

Sentimentalists. The folks who are still attached to either the process of going shopping in a local record store or the intimacy of having the CD jacket in their hands will tell you that this does nothing for them.

And then there are folks like me who can barely manage to keep their ever-evolving iPod nano playlist svelte enough to fit on their nano and instinctively cringe at the very thought of getting stuck with songs that take up more space. I think I’d pay money not to have to deal with 256 kbps audio files.

So what, Bill, you’re saying that almost no one’s going to buy these tracks and yet it still won’t necessarily represent failure on Apple’s part? That’s exactly what I’m saying. On the next iProng Radio (episode #35, available on Monday) we’ll be discussing whether Microsoft launched the Zune just so it would fail and they could go back to the shareholders and say “see, we told you it wouldn’t work, now leave us alone about it” and then go about their business of making crappy operating systems and impossibly overcomplicated productivity suites (but I digress).

I can’t help but wonder if Apple might be playing the same game here, but not with the shareholders. The record labels and several European governments have all been pressuring Apple to “open up” and sell music that can be used with a non-iPod. And a very noisy minority of users has spent the past five years publicly berating Apple for not offering music at a higher bitrate. By making these oversized DRM-free tracks available and charging extra for the “privilege” of gaining two so-called advantages that most users neither desire nor care about, and then watching as no one takes them up on it, Apple just might get to silence all of the aforementioned groups simultaneously.

While Steve Jobs’ next “Thoughts on Music” installment might not be an open letter, you can expect it to read something like this:

Sorry, record labels and governments. Sorry, audiophiles. We tried offering DRM-free 256 kbps songs through the iTunes Store, and no one was interested. We told you no one cared. We’ve been doing this for five years and we know what we’re doing. Now will you leave us alone and let us get back to doing it? – Steve