How iTunes went from simple to perplexing in 18 years

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The app that made it so easy to play music on your Mac that it transformed the entire music industry is going away, but the legacy lives on. As Apple scraps the omnibus iTunes app and breaks it up into multiple parts, AppleInsider looks at what went so right -- and then so wrong.

The many icons of iTunes through the years
The many icons of iTunes through the years


Today with our HomePods and iOS devices, it's normal to simply say aloud what we want to listen to, and to unthinkingly know that in moments it will be playing. It isn't the case that every piece of music ever recorded is instantly available to us, far from it, but it feels as if it is.

We don't consciously think about it as "digital music", either. It's just music. We'll think of it as jazz or rock or classical long before we think of it as MP3 or AAC, and that is how it should be.

It just that it wasn't anything like this when iTunes was first released on January 9, 2001.

Now that Apple is splitting up the iTunes app, it's time to see what a lightning bolt the original iTunes app was to music and to Apple. And it's time to see where -- or whether -- it went so wrong that the WWDC audience cheered to see it be replaced by Music, TV and Podcast apps.

Dark ages

By the very early 2000s, the CD was feeling archaic. You had to carry around a lot of discs, they got scratched and they got lost. It wasn't as bad as carrying a vinyl turntable with you, but it was inconvenient enough that people were turning to putting music on computer and on MP3 players.

You had to be pretty determined to do that, though. The ability to copy a CD's music onto your computer was there, the ability to play anything from the library you built up was there, and there were plenty of portable players.






Yet compared to popping in a CD and pressing Play, they were difficult to use. They weren't so impossible that people didn't do it and also turn to illegal online sharing sites such as Napster in order to get music, but it was close.

"Whatever anyone says about Apple, if it wasn't for Steve Jobs there would be no legitimate music online," Jimmy Iovine told Fortune magazine in 2009. "I think his impact on music has been extraordinary."

Apple would make downloading music both legal and simple with the iTunes Music Store in 2003, but first it had to make playing it be easy. That's what the initial iTunes app did, and it did it as part of what Apple saw as its push into the "digital lifestyle."

Behind the scenes, Jobs had thought that Apple was lagging behind. He later told biographer Walter Isaacson that Apple had been beaten by other firms introducing drives that burned music CDs.

"We kind of missed the boat on that," he said. "So we needed to catch up real fast."

Catching up by buying in

That catching up started with iTunes. Rather than invent its own app, Apple instead tried talking with the companies that made what were then two of the best MP3 apps, Panic with Audion and Casady & Greene with SoundJam MP.

According to Cabel Sasser, co-founder of Panic, Apple contacted Panic in June 2000, wanting to about "the future direction of Audion."

Panic was then in negotiations with AOL. "The meeting fully booked with Apple," says Sasser, I contacted the AOL executives so they could be involved. It seemed only fair; they came to us first and maybe this Apple meeting would make them want to snatch us up all the quicker."

This is what it could've looked like: this is how SoundJam MP appeared before Apple bought it. (Source: Macintosh Repository)
This is what it could've looked like: this is how SoundJam MP appeared before Apple bought it. (Source: Macintosh Repository)


AOL wouldn't take the meeting, Sasser tried to re-schedule it, but Apple bought SoundJam MP instead.

The first iTunes

Where SoundJamp MP was already one of the best players around, it was still too complex for Apple so the company simplified it. Apple removed an ability to change the whole look of the app, called changing skins, for instance, so that you had one single appearance and one thing to learn.

This simpler, redesigned app was launched by Steve Jobs as iTunes 1.0, running on Mac OS 9, at Macworld on January 9, 2001.






Before he unveiled it, Jobs did his usual thing of setting the stage in such a way that the Apple product appears the obvious, best choice.

"There is a music revolution happening right now," he began.

He talked a lot about burning CDs which is simply forgotten now, but back then was enormous. "People are doing this like crazy," said Jobs. "How many blank CDs were sold in this country alone in the calendar year 2000? Take a guess. You know how many? 320 million. The US census came out two weeks ago, [there are] 281 million people [in the country]."

Then he moved on to talk about how you play music on computers. He talked about the MP3 format and he showed what were then the leading MP3 software apps.

"If you look at these things, there's something that pops out right away, especially if you're not used to using them," he continued. "They are too complex. They're really difficult to learn and use. I talked to so many people using them that don't even know three-fourths of the features, because they're too complicated."

Not much updated from the one Steve Jobs unveiled, this is iTunes 2
Not much updated from the one Steve Jobs unveiled, this is iTunes 2


Just rubbing in how poor and customer-hostile all of these apps where, he also pointed out that most had restrictions such as limiting their speed or the audio quality of their music, until you buy an upgrade.

"We're going to change all this today," said Jobs," with something we call iTunes. As I mentioned, we're late to this party, and we're about to do a leapfrog."

That original iTunes had none of the restrictions he'd complained about but, more than that, you could understand it immediately. There was a big Play button, there was a list of your music. You knew what to do.

It didn't stay simple

If you used iTunes in those earliest days, you recognized that it was simple, but you probably did not recognize how much more complex it became. Since Apple added in features more or less one at a time, its complexity crept up on you.

The first change was significant but not visibly so - in March 2001, Apple made iTunes into an OS X app. In October, it released iTunes 2 and you'd be hard-pressed to see the difference, but it supported the new iPod.

You don't know anybody who has one of these now, but you did.
You don't know anybody who has one of these now, but you did.


Then version 4, in 2003, added the iTunes Store. Now you had all of your music, but also the ability to find, it seemed, just about any other track and buy it. The music player app became the music shop.

And then in what was simultaneously an obvious extension of the music store but also a peculiar move for a music player, iTunes became where you bought and played movies.

We know how the music, films and TV store forever changed how these items were sold. We now know how Apple has become a studio. Back at the start, though, the store was all about selling devices.

"The iPod makes money," Phil Schiller said in 2003. "The iTunes Music Store doesn't."

Devices and desires

It made sense for Apple to make iTunes be how you synced your iPod. You have music on your Mac, you want it on your iPod, iTunes was clearly the right way to do it. Similarly, perhaps, you could see why adding podcasts made sense in 2005. Certainly that worked out well for Apple and for all of us.

So then when the iPhone and later the iPad came, there was also some sense in syncing those too. While they both, especially the iPhone, needed to sync much more, these iOS devices had music on them.

However, if you can make a case for syncing devices, it's harder to conclude that iTunes needed to also become a social networking service too.

In 2010, iTunes, the app that plays music and video, that sells you new music and video, and which syncs your iPod and iPhone, added Ping.

At that point, the best case for adding Ping to iTunes was that Apple wanted a social networking site and iTunes was its most widely used app, the iTunes Store surely its most successful service.

Ping did have a music edge, it was meant to focus on connecting artists and listeners, and it failed. Apple dumped it in 2012, though it still hung on to some hope of social networking because then it added Facebook and Twitter features into iTunes.

Coming in cold

So just over a decade after it was introduced as this app that was so much simpler and easier to use than any other that it was a "leapfrog" product, things had changed.

Then and now. Left: iTunes 2. Right: iTunes 12
Then and now. Left: iTunes 2. Right: iTunes 12


Now iTunes was a music-playing, film-playing, TV-playing, music-buying, film-buying-or-renting, TV-buying, iPod syncing, iPhone setup and backup, podcasting lipsmacking, thirst-quenching, Facebook and Twitter app, with ringtones.

And then in 2015 they added Apple Music.

With the exception of Ping which didn't fly, and the Facebook/Twitter integration you didn't even notice, each element that was added to iTunes was good.

Then the idea of using an app you were familiar with to introduce you to new features was even smart.

It's just that both Apple and those of us who grew up alongside iTunes's expansion, could so very easily fail to see what was obvious to newcomers. If you came in cold to iTunes in 2015, say, it was a phenomenally confusing app.

That's why people cheered when Apple announced that it was breaking up the features of iTunes into separate apps.

They cheered, too, back in 2001 when Steve Jobs first announced iTunes, and if it's a shame that its demise won't be missed, the cheering was for the same reason both times.

Apple took what was a complicated thing to do with your Mac, and made it simpler. Twice.

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Comments

  • Reply 1 of 21
    iTunes should check out Roon! It's what iTunes should have been 5-10 years ago....It's the most incredible playback software ever made.....iTunes could not carry Roon's Jock strap!
  • Reply 2 of 21
    avon b7avon b7 Posts: 4,309member
    Nice piece. iTunes was a great piece of software that transformed itself into a well of frustration. It's sad that so many wrong turns were taken along the way and nobody actually took hold of the problem by the horns and shook out the crud.

    In a way it ended up being Apple's very own Word 5.

    Still. It is sad to see it go in this way.
    axcess99
  • Reply 3 of 21
    djames4242djames4242 Posts: 558member
    Fun blast from the past to see all the old iTunes icons. But... I've never found iTunes to be overly complicated or bloated. It's maybe a little confusing to have had an app with 'tunes' in its name manage books, movies and TV shows, and applications once upon a time, but that didn't make it confusing nor difficult to use. I actually liked its smart playlists and powerful database features. Little-by-little Apple has stripped functionality out, taking out some occasionally useful features like chapters (which was great for music mixes and podcasts), probably in an attempt to appease those who find it complex...
    mknelsonaxcess99watto_cobrazhiro
  • Reply 4 of 21
    djames4242djames4242 Posts: 558member
    iTunes should check out Roon! It's what iTunes should have been 5-10 years ago....It's the most incredible playback software ever made.....iTunes could not carry Roon's Jock strap!
    It looks pretty, but that's not enough to get me to pony up $120/year, unless it comes with some must-have features, and I didn't see anything particularly compelling on their site, but maybe I'm missing something.
    axcess99watto_cobra
  • Reply 5 of 21
    Jessee MichaelJessee Michael Posts: 7unconfirmed, member
    I have to admit, I'm not sure having separate Mac apps for different types of media is a step in the right direction. I get offloading iOS apps and Apple wanting you to sync through the cloud, and there could always be a lightweight desktop backup app. But having one repository for *media* files just makes more sense to me, like iTunes or Plex.
    AppleExposedaxcess99watto_cobrazhiro
  • Reply 6 of 21
    spice-boyspice-boy Posts: 1,038member
    I am looking forward to the split-up of iTunes more than any else in the next OS. Big chunks of software gone from my tired eyes. 
  • Reply 7 of 21
    dxace1dxace1 Posts: 1member
    I defected from Apple years ago amid frustration with its high-priced devices, and software.  I used Itunes Windows version for a while, but when I got hacked for $8k I stopped, and the complications of the software forced me back to the simplicity of storing all my favorite tunes on microSD.  These days you can store zillions of songs and video that way.  Too bad -- Apple screwed itself.
  • Reply 8 of 21
    hexclockhexclock Posts: 602member
    dxace1 said:
    I defected from Apple years ago amid frustration with its high-priced devices, and software.  I used Itunes Windows version for a while, but when I got hacked for $8k I stopped, and the complications of the software forced me back to the simplicity of storing all my favorite tunes on microSD.  These days you can store zillions of songs and video that way.  Too bad -- Apple screwed itself.
    Zillions you say? That’s astounding! I may have to switch to Windows since I’m pushing almost 3.8 zillion songs.
    lolliverSolidjames4242watto_cobra
  • Reply 9 of 21
    SoliSoli Posts: 9,399member
    dxace1 said:
    I defected from Apple years ago amid frustration with its high-priced devices, and software.  I used Itunes Windows version for a while, but when I got hacked for $8k I stopped, and the complications of the software forced me back to the simplicity of storing all my favorite tunes on microSD.  These days you can store zillions of songs and video that way.  Too bad -- Apple screwed itself.
    Your Windows PC got hacked and you blame Apple. I'm surprised you've only been a mark once.
    elijahgmcdavedjames4242logic2.6watto_cobrajony0zhiro
  • Reply 10 of 21
    iTunes should check out Roon! It's what iTunes should have been 5-10 years ago....It's the most incredible playback software ever made.....iTunes could not carry Roon's Jock strap!
    It looks pretty, but that's not enough to get me to pony up $120/year, unless it comes with some must-have features, and I didn't see anything particularly compelling on their site, but maybe I'm missing something.
    Yeesh, that is a ridiculous price (subscription even). Unless your life is listening to your library, no way it can possibly be worth it.
    bonobobwatto_cobra
  • Reply 11 of 21
    dxace1 said:
    I defected from Apple years ago amid frustration with its high-priced devices, and software.  I used Itunes Windows version for a while, but when I got hacked for $8k I stopped, and the complications of the software forced me back to the simplicity of storing all my favorite tunes on microSD.  These days you can store zillions of songs and video that way.  Too bad -- Apple screwed itself.
    That makes no sense, iTunes isn't even a "browse untrusted internet" thing. It's only exploit surfaces are your own computer. If you got hacked it is because you screwed up somewhere else, and I doubt they then used iTunes to gain any sort of advantage on your computer.
    Solidjames4242watto_cobrajony0zhiro
  • Reply 12 of 21
    Why? Why? Why did it take so long to fix? Users and developers have been begging Apple to break up iTunes for over a decade. In the end they did exactly as we asked and acted like it was their own brilliant idea. Hubris!
    leehamm
  • Reply 13 of 21
    22july201322july2013 Posts: 837member
    In my life I have never advised my friends or family to get iTunes. However I have advised them to get Apple Music. Isn't iTunes being broken down into three apps: Podcasts, Music and TV? Won't that cause a little confusion? Apple Music vs just Music?
  • Reply 14 of 21
    leehammleehamm Posts: 30member
    You don't mention the whole backup iceberg, that was also folded into iTunes at some stage.

    If you had music from the mp3 days, you'd likely have folders of albums containing track1, track2, track3 etc. iTunes still can't handle this, so many years later. It has to decide where to put so-called 'unknown artists' and 'unknown albums', so quite often your trackx tracks are orphaned and detached from the other tracks; grouped all together or some other ridiculous thing.

    Is there a better music app available now? iTunes is an overweight mess.

    I am not sure Apple has realized that:
    • some people don't want to stream music that they might have already paid for;
    • some people want to decide where to store their tracks;
    • we don't need multiple copies of the same album on one drive;
    • many people don't even store all their music on a local drive.
  • Reply 15 of 21
    SoliSoli Posts: 9,399member
    leehamm said:
    You don't mention the whole backup iceberg, that was also folded into iTunes at some stage.

    If you had music from the mp3 days, you'd likely have folders of albums containing track1, track2, track3 etc. iTunes still can't handle this, so many years later. It has to decide where to put so-called 'unknown artists' and 'unknown albums', so quite often your trackx tracks are orphaned and detached from the other tracks; grouped all together or some other ridiculous thing.

    Is there a better music app available now? iTunes is an overweight mess.

    I am not sure Apple has realized that:
    • some people don't want to stream music that they might have already paid for;
    • some people want to decide where to store their tracks;
    • we don't need multiple copies of the same album on one drive;
    • many people don't even store all their music on a local drive.
    I don’t understand how anything you wrote is relevant. Many of your complaints aren’t even issues with the old iTunes.
    watto_cobrajony0zhiro
  • Reply 16 of 21
    AppleExposedAppleExposed Posts: 1,694unconfirmed, member
    dxace1 said:
    I defected from Apple years ago amid frustration with its high-priced devices, and software.  I used Itunes Windows version for a while, but when I got hacked for $8k I stopped, and the complications of the software forced me back to the simplicity of storing all my favorite tunes on microSD.  These days you can store zillions of songs and video that way.  Too bad -- Apple screwed itself.

    iTunes has never been compromised. You're a hack! 
    watto_cobrajony0
  • Reply 17 of 21
    tardistardis Posts: 93member
    I have heard so many commentators repeating the story that "iTunes is Rubbish", but never understood what was so wrong. I understand that Apple added functionality along the way, although as William Gallagher says, iTunes with Music, Videos and podcasts "in 2005 ... worked out well ... for all of us", and as late as 2012, "each element that was added to iTunes was good". The story suggests that things all went wrong when, in 2015, they added Apple Music. My recollection is somewhat different. The story that "iTunes is Rubbish" became almost an accepted fact among tech journalists in the period after the iPhone became popular, and in all of the cases I have found that were actually documented, the reason was slow speed and other software failures on the Windows version. Now that most journalists use Mac laptops, you don't see so many "iTunes is Rubbish" stories. Coincidence?
    watto_cobrazhiro
  • Reply 18 of 21
    SoliSoli Posts: 9,399member
    tardis said:
    I have heard so many commentators repeating the story that "iTunes is Rubbish", but never understood what was so wrong. I understand that Apple added functionality along the way, although as William Gallagher says, iTunes with Music, Videos and podcasts "in 2005 ... worked out well ... for all of us", and as late as 2012, "each element that was added to iTunes was good". The story suggests that things all went wrong when, in 2015, they added Apple Music. My recollection is somewhat different. The story that "iTunes is Rubbish" became almost an accepted fact among tech journalists in the period after the iPhone became popular, and in all of the cases I have found that were actually documented, the reason was slow speed and other software failures on the Windows version. Now that most journalists use Mac laptops, you don't see so many "iTunes is Rubbish" stories. Coincidence?
    I don't recall what journalists were saying circa 2001, but I remember anti-iPod users saying that the iPod and iTunes were rubbish because Apple organizes your music for you. They claimed that the best way for all users to control their music was to have a file system in place. Sound familiar?

    I think they also wanted Ogg support, saying that it was better than anything from the iTunes Music Store. I recall one person I knew using Limewire to download MP3s to then convert into OGG and then claiming they now sound better. 🤦‍♂️
    watto_cobrajony0
  • Reply 19 of 21
    majorslmajorsl Posts: 119unconfirmed, member
    Ah, I remember SoundJam.  We don't much care now, but back then we could "skin" it.  There were some really cool and crazy ones.  One was like a Steampunk theme dialed up to 10.  Someone also took the hockey puck mouse look and made it into a skin that worked really well and looked good too.  Memories...
  • Reply 20 of 21
    tardistardis Posts: 93member
    I have heard so many commentators repeating the story that "iTunes is Rubbish", but never understood what was so wrong. I understand that Apple added functionality along the way, although as William Gallagher says, iTunes with Music, Videos and podcasts "in 2005 ... worked out well ... for all of us", and as late as 2012, "each element that was added to iTunes was good". The story suggests that things all went wrong when, in 2015, they added Apple Music. My recollection is somewhat different. The story that "iTunes is Rubbish" became almost an accepted fact among tech journalists in the period after the iPhone became popular, and in all of the cases I have found that were actually documented, the reason was slow speed and other software failures on the Windows version. Now that most journalists use Mac laptops, you don't see so many "iTunes is Rubbish" stories. Coincidence?
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