
   This was a long time ago, and iTunes has gotten long in the tooth.       (Reuters/Robert Galbraith)
     
Around 10 years ago, exasperated by a roommate’s tech 
woes, I convinced the guy to dump his Windows laptop for a Macbook, 
promising that if he’d switch, I’d be his tech support for life. At that
 point, I’d been an Apple user for six years, and had showed him over 
and over again how “it just works” was just fact. I never had a virus to
 speak of, never had a problem with an audio or video card, and had 
never been personally crippled by a blue screen of death.
But in hindsight, after a decade of phone calls, emails, 
walk-throughs, and being treated like a walking, talking FAQ, I’m 
admitting defeat. Converting him and many other people to Apple may have
 been a bad idea. Of course I’m saying this after his latest 
question—“How do I put music on my iPhone?”—nearly made me throw my 
iPhone at the wall, a heck of a way to end the call.
Don’t blame my exhaustion on my friend’s 
lack of technological know-how or my own dwindling patience. Blame 
iTunes. Once the ultimate in music file management and the centerpiece 
to Apple’s financial turnaround, this program has evolved from a simple,
 dependable music player into the biggest example of bloatware in 
computers today. But why mince words? I hate iTunes. And I think Apple 
does, too.
 To figure out where this once-stellar program went so terribly wrong, you have to look at how it got to where it is today. To
 figure out where this once-stellar program went so terribly wrong, you 
have to look at how it got to where it is today. Billed as a digital 
jukebox, iTunes launched in January 2001 at Macworld in San Francisco. 
“Apple has done what Apple does best—make complex applications easy, and
 make them even more powerful in the process,” said Apple CEO Steve Jobs
 at the time. Just nine months later iTunes 2 came out, landing 
alongside the iPod, the MP3 player that forever changed music.
iTunes 3 came and went, and in April 
2003, iTunes 4 landed as a monumental upgrade, introducing the iTunes 
Music Store, as well as rolling out video support and Windows computer 
compatibility. The importance of these improvements can’t be overstated 
for Apple’s financial success, as well as for the evolution of digital 
media at large. With iTunes 4, millions of people were suddenly granted 
instantaneous access to digital downloads on demand. Apple famously sold
 1 million songs in the first week, and 25 million by the end of the 
year. People were buying music again, no longer stealing it from the 
web. The Apple music ecosystem worked well, and everyone was happy. 
(Well, everyone except for Kid Rock.)
But as Big Download got rolling, so too 
did iTunes. Movies, television shows, and music videos arrived for sale 
with iTunes 6 in 2005, and with them came new tabs in the program for 
managing that content on devices. But as Apple pushed out new 
generations and models of iPods, iTunes also became a device manager—and
 not just for Steve Jobs’ gizmos. An awkward relationship between Apple 
and Motorola resulted in ROKR, SLVR, and RAZR, the Huey, Dewey, and 
Louie of music phones, and those too were administered by the jukebox 
app. Nike+ interacted with iTunes and iPod Nanos. AirPlay connectivity 
was rolled into the application, and compatible speakers could connect 
to the program. Front Row, a slick media management skin, even 
premiered—just long enough to get pushed to the background when Apple TV
 (also an iTunes joint) appeared with iTunes 7. 
So in just a few generations, iTunes went
 from being a svelte piece of software to an octopus of an 
application—and with that, an array of problems began popping up. iTunes
 7, for instance, saw 18 updates in less than 12 months. Likewise, 
iTunes 10 (with Ping!) had 19 updates in a year. iTunes 11, meanwhile, 
needed 17 patches in its 11 month life. On the bright side, things are 
looking better for iTunes 12—with only three releases since its rollout 
in October—but the launch of Apple Music could easily upend that. So, as
 we all laugh at Flash for its seemingly bi-weekly parade of upgrade 
prompts, it’s fair to ask if iTunes is any better.
All this history sidesteps the injection 
of the App Store into iTunes. With the launch of iOS 2, iPhone owners 
needed somewhere to download their various digital goodies from, and 
someone in Cupertino thought it would be a great idea to make iTunes 
that place. In the end, this decision will prove to be a fatal mistake 
for iTunes because it didn’t merely add another category of media to the
 already chubby program, it actually introduced a whole new realm of 
computing. And the effects of apps in iTunes have rippled across Apple’s
 Mac OS, from the small and annoying (like how clicking on an app’s 
webpage springboards iTunes to open, an undesirable effect that can take
 minutes to unfurl because the program now opens like a rusty zipper) to
 the potentially problematic (iTunes glacial performance has to be 
pushing casual listeners away from their owned digital media towards 
more nimble music experiences like Pandora and Spotify—I know it’s made 
me quit opening iTunes, listening to my music, and potentially buying 
more). 
 Apple Music’s launch marks a last ditch effort by the company to stay in the game. And
 though Apple has pocketed billions during the swelling of iTunes, it 
might not work out so well for Apple in the end. Apple very nearly 
missed the boat as streaming music has supplanted selling it. Apple 
Music’s launch marks a last ditch effort by the company to stay in the 
game. They may never reach the music download revenue that they once 
did, but then again, neither will anyone else. And since the money has 
moved from owning to listening, the company is trying its hardest to 
make sure they can capture as much of that transitioning market as they 
can.
And this is essential for Apple because 
while music may not earn the company much money, it makes for great 
marketing. For instance, last year Apple’s gross income was just over 
$70 billion. During that time, iTunes generated $10.2 billion in net 
sales, despite a decline in digital music purchases. Though the company 
doesn’t provide a breakdown of apps versus media sales, the company 
noted in its 2014 annual report that iOS software has taken over what’s 
really driving iTunes now. 
By comparison, hardware brought in more 
than a $158 billion dollars. While margins vary between media, software,
 and hardware (it even differs for iPhones, iPads, Macs, and iPods), 
using napkin math on Apple’s 70/30 profit-sharing split would ultimately
 push roughly $7 billion in profit from iTunes toward the bottom line. 
From there, keep in mind that apps are king, and you could estimate a 
modest $3.5 billion (if that) comes from music sales. To most companies,
 it’s not chump change, but to Apple it’s only 5% (again, if that) of 
their haul. 
But this chunk of change is even more 
valuable when you turn it into a marketing machine. Whether it’s by 
squabbling with Taylor Swift or making up with Eminem, music is what 
keeps Apple socially relevant. And just ask Samsung—that’s something 
that money can’t buy. Because the real story behind Apple’s success 
isn’t so much music as it is stuffing hard drives past their capacity. 
Filling the storage space on Apple devices is key to getting consumers 
to buy new ones. How many times have you heard someone say that they 
need a new phone or laptop because their current one was full?
With the slow death of iTunes and the 
decline of purchased media, Apple has had to find new ways to make that 
happen. Doubling the size limit on apps from two to four gigabytes 
certainly helped, as did bulking up the size of iOS itself (temporarily 
crippling many eight gigabyte iPhones, a black eye for Apple). What’s 
stuffing phones, tablets, and computers fastest is user-generated 
media—photos and videos. As many a parent will attest, no gigabytes are 
enough to satisfy the appetite of Apple’s great iPhone cameras. But one 
problem for Apple is that this kind of media doesn’t pay. That is until 
the company launched its iCloud Photo Library, which guarantees the 
company a subscription revenue stream from people who have sign up. And 
why wouldn’t they? By putting your photos in the cloud, they remain safe
 and can allow you to fill your phone with more apps and media (for the 
few who still actually buy it).
 Apple’s new music offering will show up in an updated version of—you guessed it—iTunes. Which
 comes to this week’s news, the release of Apple Music. Free to stream 
for the first three months, and easy enough to get hooked on after that,
 on the desktop, Apple’s new music offering will show up in an updated 
version of—you guessed it—iTunes. Never mind that it will appear on the 
Music app on iOS (or that the Mac OS has aped Apple’s handheld apps with
 Mail, Maps, Photos, etc. appearing on computers). Instead, Apple is 
just stuffing something else into iTunes. Again.
So open up iTunes, if you can, and enjoy 
Apple Music. And while you’re in there, try to quickly put some of your 
old tracks onto your iPhone. In trying to tell my friend how to do it, I
 didn’t know what to say. Yes, I know there are a variety of ways to 
load up your library, but the guy has a legitimate gripe. He bought some
 CDs in the 90s, ripped them, and wanted to just pop a couple tracks 
onto his new phone—how hard could that be? If it “just worked,” he 
shouldn’t have to ask how to do it. But somewhere along the way, iTunes 
stopped just working. Instead, it started selling.
Ultimately, I told him to do what everyone else is doing—sign up for Spotify.