Apple’s Five Biggest Music Failures

There’s been a lot of rhapsodizing about the successes Steve Jobs had with Apple as CEO.  And rightly so.  But those victories obscure Apple’s failures, the occasions where products didn’t live up to the hype or the shortcomings of which were/are glossed over because of Steve’s reality distortion field.

Listen, no one bats 1.000.  But if you don’t examine your mistakes, how can you ever learn to get better?  Apple learned from Lisa, the OS software licensing fiaco and the Newton.  So why have then not learned from these missteps?

Here are my picks for Apple’s five greatest music-related failures.


 1.  iTunes (Introduced 2001)

My first choice will be lambasted as heretical by the fanboys, but if we’re all honest about it, iTunes is a mess.  It’s big, bloated and doesn’t always play nice with large libraries.  But because it’s the only interface between your libraries and your iPod/iPhone, we’re stuck with it.  Hey, Apple!  How about an iTunes Lite?

2.  Motorola ROKR (Introduced 2005)

The iPhone wasn’t Apple’s first attempt at a cell phone.  The ROKR featured an MP3 player that had an iTunes-like interface but only allowed the user to upload 100 songs at a time.  Oh, and the transfer times were slower than the orbit of Pluto. Fortunately, Apple had the iPhone in the pipeline and the ROKR was soon sent to the landfill.

3.  The iPod Hi-Fi (Introduced 2006)

Basically a glorified iPod dock, Steve famously declared that after hearing music through this thing, he was going to throw out his high-end stereo system.  But it was expensive (more than the superior Bose SoundDock), heavy and not all iPods could be connected.  It was discontinued by the fall of 2007.

4.  Ping (Introduced 2010)

Apple tried to bring social networking to iTunes with the half-baked Ping.  I signed up as soon as it was available but I haven’t been back in months because it’s not even remotely “social” in a universe that also contains Facebook, Twitter and Google+.  FAIL.

5.  The High Price of Licensed Accessories (Ongoing)

I needed a new case for my iPhone 4, which meant that I had to shell out more than $30 for a piece of plastic that must have cost less than 25 cents to manufacture.  (It only looks like the carbon fibre Ferarri case pictured above.)  Yes, the market will bear that price because people are willing to pay premium prices for accessories that go along with premium products.  And Apple is smart.  They demand hefty licensing fees on third parties (like Griffin) in exchange for allowing them to make these accessories.  But the price of such things as iPod and iPhone cases is nothing short of Sopranos-like usuriousness.

Alan Cross

is an internationally known broadcaster, interviewer, writer, consultant, blogger and speaker. In his 40+ years in the music business, Alan has interviewed the biggest names in rock, from David Bowie and U2 to Pearl Jam and the Foo Fighters. He’s also known as a musicologist and documentarian through programs like The Ongoing History of New Music.

5 thoughts on “Apple’s Five Biggest Music Failures

  • August 28, 2011 at 4:24 pm

    With iOS 5, iTunes (or more appropriately a PC or Mac) won't be required as you can use the iCloud.

  • August 28, 2011 at 4:27 pm

    I had the Motorola ROKR, didn't use the "iTunes" feature much as I couldn't stand using iTunes on my PC as the gateway. As for iTunes, Sony had a much better program, SonicStage – I don't think its available anymore as it seems to have died with Sony's ATRAC3 format & Connect store. But the cataloging feature was miles above what iTunes has. I've got well over 500 albums ripped onto it, sorted by Artist, then by album (chronologically).

  • August 28, 2011 at 7:58 pm

    One thing that should improve iTunes is wireless syncing (i.e. the iCloud service mentioned by Opp above). Still, there are too many features and too much bloat in the program. I wish there was a stripped down, lite version.

  • August 29, 2011 at 12:48 pm

    I had a ROKR as well, and didn't mind it.
    But MAN, it took forever to upload. I though at first it was my very old computer.
    However, I soon learned that it was just the program on the phone.
    It may have seemed like a big number at the time, but 100 songs was not very much at all.

    But it was my first MP3ish device, so it will always hold a special place in my heart.


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