The Leaning Tower of Ping: How iTunes Could Be Apple’s Undoing

With each new product that Apple announces, including the revamped Apple TV and the new Ping social network, Steve Jobs reveals a little bit more of his plan to dominate the media universe. But I can summarize that plan’s fatal flaw in one word: iTunes.

Don’t get me wrong. I think Apple’s hardware is unbeatable, and my admiration for it has only grown since I got my first iPod back in 2003. My home/office is virtually an outpost of the Apple Store: with the exception of the TV, the videogame console, and the coffeemaker, almost every device in my house is an iGadget of some kind. The operating systems that power my Apple devices are pretty good, too. I love OS X and I’m very glad that Xconomy is a mostly Mac shop. On the mobile side, Android is impressive, but iOS is the slickest and most user-friendly mobile operating system out there, in my judgment.

itunes-10-logoBut there’s one piece of the Appleverse that I’ve always detested, and that’s the desktop version of iTunes. The ugly duckling of the iFamily, this program is hard to understand, hard to use, inelegant, and ill-behaved—in short, the very opposite of most other Apple products. I dread booting it up every day, yet I can’t sidestep it. What makes iTunes’ deficiencies so infuriating is that the program is indispensable: it’s the nerve center that stores all of your Apple-related media content, mediates all of your Apple-related purchases, and connects all of your Apple devices.

The rollout of iTunes 10, the latest “upgrade” to this nearly 10-year-old program, was one of the two centerpieces of Steve Jobs’ keynote talk on Wednesday, the other being Apple TV, of which I’ll say more in a moment. And the big new feature of iTunes 10 is Ping—a Facebook-like social network designed to help users discover music by seeing what their friends are buying for their iPods.

I’ve been playing with Ping, and it seems to have most of the features you’d expect of a media-centric social network circa 2010—profiles, friending, news feeds, comments. Plus, of course, you can easily preview or buy the songs or albums mentioned in your friends’ news feeds. It’s easy to see how Apple might expand Ping beyond music to facilitate conversations around media of all sorts, including movies, books, and mobile apps.

itunes-pingThat said, Ping has some serious limitations that, to me, are symptomatic of the larger problems with iTunes. For example, there’s no integration with Facebook or even with your contact lists, so it’s virtually impossible to find real-world friends to connect with. For a social networking tool, this is a bit of a problem. (Kara Swisher at AllThingsD grilled Steve Jobs on this very issue, and his suggestion for finding friends was to “type their names into search or send them emails inviting them to join.”)

And there’s an even bigger issue: Adding a social networking interface, on top of all of iTunes’ other functions, is like grafting another limb to the forehead of an octopus. It’s just too much.

Few people may remember this far back, but iTunes predates even the iPod. It started out in early 2001 as nothing more than a program for ripping CDs and playing the resulting MP3s from your computer. (It was based on … Next Page »

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Wade Roush is the producer and host of the podcast Soonish and a contributing editor at Xconomy. Follow @soonishpodcast

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  • Fred

    What’s a Zune?

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  • I’m amazed at, and grateful for, all the comments on this story today. Clearly iTunes works just fine for some people, which is great. Others seem to share my frustrations with it. At least the piece seems to have hit a nerve.

    @Bill D: You wrote ‘So in one breath you’re complaining about all the utilities Apple jammed into iTunes, and in the next you’re complaining that you have to switch to iPhoto to synchronize photo albums while iTunes synchronizes everything else. Which is it?” I was trying to point out what I see as one of the weaknesses of iTunes — its inconsistency. It purports to be the manager for all your media, but then for no apparent reason it excludes photos.

    @Mark Strait: You and a couple of other commenters suggested that I shouldn’t criticize iTunes if I can’t come up with a better program myself. Balderdash. That’s like saying I shouldn’t be allowed to write critically about a Monet if I can’t paint or about a Charles Ives symphony if I can’t compose.

    To put it simply: I can recognize good or bad software engineering because well written programs make me happy and bad ones just make me want to hurry on to my next task. iTunes is one of the latter. Most Apple products make me happy, and I’m curious about why iTunes is so different. It makes me wonder whether this program, in its current form, is well suited to be the lynchpin for Apple’s whole media strategy.

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  • iTunesuser

    I’ve never understood people who find iTunes ‘confusing’. Honestly, you’d have to be a moron. And to call it ‘inelegant’ is pure fantasy.

  • If you had to start up a new program to preform each of these functions it would be a nightmare.

  • David b

    Your criticizing a product of a company that throws away more ideas and prototypes than it keeps. you can be sure that for every iTunes approach and feature that sticks there are probably three that are tossed. You level some general criticisms without really making any real specific substantive points. neither do you have a clue about solutions to your gripes. which features do you want to thow away? apple is the only company I know that takes huge risks in making a current very successful product old stuff with a new one. iTunes will be no different when it is time.

  • Tim

    How is iTunes hard to understand or hard to use? Seriously. When you open iTunes what do you want to do in it that you have to stare at the buttons for minutes on end trying to figure out what to do?

    I’ve been using iTunes since the very first version and even back then I didn’t find it confusing, and I certainly don’t now.

    Perhaps you shouldn’t be writing about technology if you find a program like iTunes difficult. Have you tackled Address Book yet?

    All kidding aside, even on the other aspects you mentioned, I don’t get it. iTunes is the one program that I don’t think has ever once crashed on me. It always does what I tell it to do and seems to do it quite well. I’ve never lost any songs, movies or had my iPod corrupted while using it, or anything else untoward.

    Yes, it’s a workhorse that perhaps it got a tiny bit of ugly paint slapped on it in version 10, but it still works for me and I’m guessing a lot of other people too. If it weren’t, I think Apple would have a vested interest in overhauling it. (And they do that, don’t forget about the new Shuffle.)

  • Mike Campbell

    Interesting article but I must be using a different product.

    I think that overall iTunes is great & it’s free.

    On a Dell 390 with XP SP3 I have a 120GB iTunes database. 50/50 music/video plus Podacsts etc.
    Syncs flawlessly with an Apple TV (I want a 500GB Apple TV but fat chance).
    Syncs flawlessly with 22 iPods, 4 iPhones, an iPad (back up is SLOW).
    Purchases via iTunes Store are also flawless, plus have a ton of Apps.

    Also installed on other PCs & three Macs.

    Overall I give it 9 out of 10.

    Mike Campbell – Brighton Marina, UK
    (Age 61. 40+ years in IT & have used everything. I don’t work for Apple)

  • Mike Campbell

    Having now read Wade’s article in detail, & the huge variety of responses, I should like to add these comments which may assist some readers:

    iTunes Specific:
    Superb training at
    iTunes 9 Essential Traing by Garrick Chow
    Anything by GC is worth watching

    Any iPod book by JB at

    And, of course, RTFM !

    Digital Hub:
    Get a decent Mac or PC as your main “digital hub” to which all other devices link.
    Supported by a modern communications infrastructure ie. fast Broadband/Cable & WiFi “n”.

    PCs & Macs should be 2GB-4GB RAM, big hard drives 7,200rpm
    Decent Security Suite & Firewall stuff
    Load the minimum apps at Start Up
    Then BACK UP, BACK UP & BACK UP, especially before any upgrades, plus System Restore for PC.

    Get an IT Mentor, free/fee.

    Follow all of this & the world is your oyster….
    Sadly, nobody ever listens.

    As an aside, I speculate that Apple will do a complete iTunes rewrite or overhaul within three years. They did it for Macs with OS X.
    With 160M iTunes Credit Card Accounts in 23 countries they’ll have to get it right – FIRST time.

    Good luck everyone
    Mike Campbell – UK

  • Bettie

    I’m new, using a Dell laptop. I first encountered iTunes a few months ago, version 9.
    I love it. It does all sorts of things that I’d been trying, with difficulty, to do with separate programs, and does them very well indeed.
    So shut up. You’re doing a silly, techie rant.

  • In the same essay you quote, Stephenson also confidently predicts that within ten years, Linux will completely replace Windows and the Mac OS. This was in 1999.

    When I read someone quoting Stephenson, I immediately reach for the salt shaker, because I know it’s going to take much more than one grain. :)

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  • davesmall

    I like iTunes and don’t share any of this author’s views. I have several iOS devices including an iPhone and iPad. I plug each device into the USB port on my laptop once a day and get automatic backup, a battery charge, App updates, and anything else iTunes might have that I want that day. I already have wireless sync for the items that change frequently via my MobileMe account. I don’t see a benefit to wireless syncing for app updates and media downloads because USB is faster and I need to charge the battery and make a backup anyway.

    I don’t see any value to Ping. But then I don’t see any value to Facebook either.

  • Arby

    I have no problem with iTunes being the “jack of all trades” for media, but it DOES have some weird unintuitive ways of doing things, some unintuitive UI here and there, and worst of all, it’s not a “fast” and responsive app. Compared to everything I run on my 2.6 quadcore, it’s the clunkiest. Just managing iphone apps via iTunes reminds me of the old days of using Windows 3.1. We’re talking sluggish!

  • Patrick

    Lately it is very fashionable to bash iTunes in the blogosphere. I really can’t understand it. Compared to software like Microsoft office, iTunes is very fast and uncluttered. It fulfills its mission very capably. I will admit that iTunes 9 had some minor stability problems and some issues syncing iPhone content, some of which were a bit frustrating. However, from what I can tell, iTunes 10 fixes all of these problems quite well. iTunes 10 is also quite fast. I guess people just like to bitch about things…

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  • Dave

    It looks like everyone thinks you’re full of shit. You probably have a good point, you just chose the wrong argument. iTunes tries to do too much but does an okay job of it. It is not the best place for a social network but when that network requires so much integration with your music, there is nowhere else to put it that makes any sense. So just accept that iTunes now does one more thing that it perhaps should not do. If they renamed it to iKitchenSink, would that make you feel better about it all?

  • spooky

    I’m not crazy about iTunes either. In a lot of respects it’s great but with stuff like syncing your iPhone… it’s majorly annoying.
    Like… plug in your iPhone and press through multiple tabs to sync your movies, photos, apps etc… then halfway through you decide to buy a song… so you have to wait while iTunes starts syncing first and locks everything up.. then it’s multiple tabs and windows again… back to the sync…. then you finally think you’re finished and hit SYNC and go to bed. Next morning you discover a warning window saying there isn’t enough room on your iPhone to fit all the songs…. so then you end up scrambling to try and get it synced up before you head out to work.

  • Scott

    I find there is a trend in relation to the people who hate iTunes and tge people that apparently own pc’s. I own a MacBook pro, and the only time I have to load iTunes is after an update, otherwise my Mac stays on 24/7. I never find that iTunes is slow to respond, even after an accumulation of over 100 gigs of media. It never crashes, even with many other things going on in the background, syncing my phone, using the iTunes store, so on and so on. And as for the “inconvenience” of having to open iTunes to sync your phone? Remember the days of your first cell? Zero interfacing with your computer. No backups, no software tweaks, nothing. You’re becoming spoiled.

    If all these problems only seem to be related to pc’s, maybe the problem isn’t the program. If a cd plays fine in one player but skips in another, should you blame the cd, or the piece of trash your playing it with?

  • MH

    I run a windows PC and iTunes is the only program that ever crashes. For the person with the CD analogy, if your player plays every CD okay except one perhaps it is the CD. I would love to be able to sync my iPhone and iPod with another program, but sadly cannot.

    I have not used iTunes 10 long enough to have an opinion on it yet. I did turn on Ping for a day, but all I saw were “win a free iPhone 4” ads, so I turned it off.

  • Eric Schatz

    So is this an application or isn’t it really a multimedia operating system?

  • @MH I run hunreds of Windows PCs and iTunes is one of the few things that doesn’t cause problems. The whole purpose of Windows is it’s a cash cow for the enormous support, maintenance, training, service, and security industries. Windows has made its fortune on how bad it is. Why are you using something that crashes all the time anyway?

  • John

    These criticism cover a lot of ground, and are inconsistent (sometime too many features, sometimes not enough). Perhaps they should have been broken into several different blog posts to bring some order to the criticism madness :).

    Seriously, though – reading this, I wondered what programs you’re using. iTunes manages synching to the various Apple devices and plays and organizes media. I’ve yet to see anything else that does that better. Asking it to manage photos would be like asking it to manage addresses or calendards, which is dumb, because you can do that far more easily thought the various Apple apps OR Google OR Exchange OR yahoo OR MobileMe.

    I can’t think of much software I use daily that’s as straightforward as iTunes.

  • James Z

    don’t know what you’re all talking about, iTunes works fine for me. user friendly enough, more than anything else you can find out there anyway.

  • LAViking

    Jered, quit being such a hater. OMG!! Aside from wireless syncing iTunes (a feature I hope is added soon) iTunes does a an excellent job. Are you sure you’re not a Fandroid Troll?

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  • Eddietec

    Put me on the list that iTunes runs great. Not issues at all and waiting for APPL to add more features :) Sure, it runs on a Mac.

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  • As you can read from my post, I finally have gotten some actual directions from Apple about how to proceed getting a profile approved for an Indie artist and I have a contact email for people to write to:

  • Felonious Munk

    Yeah, you’re right.
    To paraphrase Winston Churchill:

    ITunes is the worst on-line service.
    Except for all the others.

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  • Paul Moloney

    “I don’t recall hearing a practical alternative”

    Umm, Media Monkey? I’m new to the Apple market having only just bought an iPhone. I can’t believe how intuitive iTunes is (especially as the iPhone is so intuitive). It’s like 2 entirely seperately companies made these. Honestly, try MediaMonkey for transferring music, try iTunes, and then try to tell me that latter is better.

    Hoards of fan boys bashing me in three, two, one…


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  • dymaxion

    Apple will never “get” the web. They killed Lala and still don’t have a simple web based interface to iTunes.

    After their handling of Lala I will never purchase an Apple product. Its just another way to get screwed

  • Jered

    @dymaxion: The most valuable part of this comment thread, for me, has been the claim that “Apple promised the labels that their music would never go on the web,” which is a thoroughly plausible reason for the embedded not-quite-web experience in iTunes, the application bundling, and so forth.

    I’m quite curious now if this is true, and there is a contractual reason for the messy bits of iTunes. Wade, up for some investigative journalism? :-)

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  • I am surprised to see so many people trying to defend iTunes within these comments!

    I used Windows XP, so it’s probably different from OS X users. But, iTunes uses like 80 megs of RAM while it is OFF! It runs three background processes when I start the computer. This is unfortunate since I have a Dell Mini 12, and don’t have a lot of resources to spare. But, I do have an iTouch which I happen to like.

    In terms of functionality, I have had bizarre experiences just using this program to sync my iPod. Sometimes it works, sometimes it doesn’t. Sometimes I need to try multiple times, and after the 3rd time, it finally puts on my new files, even though I did everything the same every time I synced (that is, I clicked the “sync” button and then waited)

    I actually recently decided to launch a blog dedicated to how much I hate iTunes. (link provided above)

  • Lk

    “I think Apple’s hardware is unbeatable, and my admiration for it has only grown since I got my first iPod back in 2003. ”

    I stopped reading, my dog is a better tech journalist than you.
    Your editor should be ashamed of hiring this kind of people

  • @Lk: If you’ve got a dog who’s a better tech journalist than Wade Roush, then I’ve got a desk, computer, and 401k for your dog.
    Sincerely, Wade’s editor

  • Travis

    I hate iTunes because it is ridiculously slow.

    I have a very large media library. Multiple terabytes of iTunesU, music and movies, much of it stored on network drives.

    iTunes takes several MINUTES to load on my computer, which is a modern spec PC running Windows 7, and a fast wifi-N network.

    Syncing my iPod Touch is a very frustrating experience because every little click I do in iTunes causes another long wait while iTunes goes to the network drive to fetch heck only knows what data.

    iTunes is horribly unreliable. If I download content directly onto my iPod using the iTunes Store accessed on the device, there is only a 50/50 chance that the content will be correctly saved to my hard disk when I next Sync it to iTunes. It removes the content (despite me flagging the option that I’ll manage that stuff myself) and then I find that only some of the lectures are on my hard disk. The entries appear in iTunes, but the files aren’t found.

    I’ve lost many gigs of iTunesU stuff that way, had to redownload it.

    I use iTunes to download iTunesU content, that’s the main thing I do with it. As I prefer to organise content myself rather than rely on iTunes’ weird folder structure in the iTunes directory it would be much easier for me if I had just a nice, lightweight, slim program for syncing a directory of content dragged and dropped onto my iPod.

    And I did have such a program… Sharepod.

    But Apple’s gone and screwed that up for us by making changes to the iPod’s data structure, making Sharepod and several programs just like it useless again on iOS4 devices, until the programmers can figure out how to write to the iPod again without making a mess.

    Sharepod was fantastic. It would load instantly, copy media to or from my iPod quickly and without any fuss, giving me control over what exactly I put on there without having to worry that I still had some old Podcast episode which for some reason kept copying itself back onto my device despite repeated attempts to stop it, etc.

    I strongly suspect that Apple deliberately made these changes just to stop people from using Sharepod etc.

    It’s one thing to have their own program to do everything, it’s another to deliberately wreck other programs so that everyone will be forced to use theirs.

    I love my iPod, it’s a great little gizmo, but Apple’s conduct with respect to their app approval process, their inconsistent censorship policies, their frequent breaking of third party software and hardware to force people to use the Apple Product etc is far more intrusive than anything MS was ever up to, back in their bad old days when they were seen as a bunch of corporate bullies.

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  • iTunes sucks

    I have a brand new Windows 7 laptop (Core i5 430M with 4GB DDR3 RAM and an SSD) and I just installed iTunes 10 on it. I erased all the content off my iPod then tried to drag three mp3 files into iTunes. iTunes hung and since then every time I open it it instantly hangs. Wait, now as I’m writing this, about 5 minutes later it doesn’t appear to be frozen anymore but I still can’t add anything into my library–nothing happens when I drag and drop files.

    iTunes is the biggest pile of junk software ever conceived. How hard can it be to copy over a handful of mp3s and a few GB of mp4s to an iPod Touch with iTunes? I’m glad I found an mp3 player that supports MSC mode so I can just drag and drop files to the device in any OS without having to install and use crapware to do it. What an innovation; just simply drag and drop files onto your device like a hard drive. Amazing Apple didn’t think of it.

    Unfortunately I still need my 64GB iPod Touch for mp4. I’ve tried running iTunes in VirtualBox, in Wine, and also tried ifuse/gtkpod and no go. So I’m stuck with this PIECE OF GARBAGE iTunes software until I find a descent alternative for an iPod Touch I guess.