Mac switcher reaches the "wow, iTunes sucks" brick wall

The excellent Charlie Brooker is going through all the standard stages of the Windows-to-Mac transition. First mocking them as toys, then not caring about their superiority, he ultimately embraced the truth and made the leap. He has just reached the first stage of post-Switch Apple Zen: accepting that iTunes is a turd that hasn't moved on from the DRM era of media syncing. He is also evidently on the threshold of "skeuoomorphic design is nauseating."


  1. I have two partitions running OSX but only one has iTunes for my iPod Touch.

    For the other partition I use VLC, a significantly much better media client.

  2. Isn’t iTunes’ suckiness platform agnostic? If he had any Apple device he must have known the hurt before switching.

    1. @LeSinge I’ve always thought it was cross-platform suckiness, though the degree of suckiness is higher on Windows than on OS X. Still: suck is suck.

    1. I agree with you regarding open source software on OS X, but Songbird (at least on OS X) is not that great. It’s what I use, but I don’t really consider it better than iTunes. I use it because my music collection is on an external hard drive connected to a linux server on my network, and iTunes doesn’t handle that kind of situation very well. The UI of songbird is quite bad, and that’s besides the fact that it doesn’t integrate visually or tactile-y with OS X, and scrolling with an Apple touchpad is jerky and useless in it (same with Steam and some other cross-platform software, FWIW).

      My favorite music program UI was Amarok 3.x on linux. They ruined it in 4.x and made it more like Songbird (and itunes, which is similar). It was kind of similar to Winamp’s original music library interface, combined with the old-school winamp direct playlist interface.

      That said, while I copy music manually directly to my Nexus One, and before that a Cowon MP3 player that allowed the same thing, I understand the sync model that iTunes uses. In an ideal situation, I would probably prefer that model. But when you’ve got 50 gb + of music, stored on a computer other than your main one, and your portable device has nowhere near that much storage to devote to music, the sync model and central iTunes library system falls apart.

      For most people, I imagine it works just great and is much easier to deal with.

      1. If you didn’t like the transition from Amarok 1.4 to Amarok 2 you might like Clementine which is a port of Amarok 1.4 to Qt 4.
        It allowed me to get rid of all the Qt 3 stuff I had on my system only to keep Amarok 1.4 running.

      2. re: Amarok – have you tried Clementine (cross-platform)? It’s based on earlier Amarok and is my current favourite UI.

  3. You think Booker would ever write anything else?

    Leave iTunes on all the time, like you would any media server.

    Plug in your phone, drag and drop media, done.

    And like any ecosystem (sony, windows media), you have to have the right format, so if you can figure out the difference between an avi and an mp4, and the simple ways to convert, its really easy.

    And to the constant noise about different media formats, it’s been changing since day one.

    And the DRM canard Booker plays in disingenuous at best.

    Ask someone like Glenn Fleischman.

  4. What’s Apple’s rationale for not supporting synching via wifi? They must have some kind of pretext, however paper thin it may be, for requiring me plug my ipod into the computer to transfer podcasts and upload my pedometer data. Right?

    1. I jailbroke my ipod so it could sync via wifi, and let me tell you, it’s incredibly slow! I mean, so much so i couldn’t bare it anymore and had to attach the USB cable and do it manually.

    2. I am not an expert, but I suppose there are security/privacy/bandwidth benefits when using USB. It’s not that easy to intercept USB as you’d need dedicated hardware attached to or software running on the host computer and neither would probably go unnoticed by the user and it seems that you can pretty much use your own protocol on top of USB.
      WiFi or Ethernet on the other side are trivially easy to intercept, to a certain extend even with Mac OS X on-board means.

      Obviously there are also monetary benefits: If you lose your cable, you’ve got to buy a new one from Apple and third-party hardware vendors probably pay royalties for the right use Apple connectors and protocols in their accessories.

  5. His experience seems to jive with a non-Apple user making the jump, However I’m not sure what is meant by the phrase “hasn’t moved on from the DRM model of media syncing” in this post.

    Why wouldn’t you want to sync your media to your devices so you always have a central backed-up source – though yes, managing that can suck depending on many factors. But there is no other way to manage multiple device libraries from one place and have any control, e.g. your music player and your phone can share the same playlist, or not depending on how deep you want to go.

    As to DRM it’s always worded that it’s Apple’s fault for supporting it, despite that fact that Apple publicly and famously called for DRM to be abandoned (link dead unfortunately). Like any distributor Apple has to abide the contractual demands by the obviously paranoid and late to the digital party music industry. When contracts go Apple’s way they use iTunes Plus which as I understand it uses a meta tag stating the purchaser’s name that otherwise isn’t enforced. A nice compromise IMO.

    iTunes as a syncing hub is probably the result of growing pains. It’s always seemed so unlike Apple that their music player became the engine for mobile devices that do much more than play music. At least the new App Store is a standalone thing and hopefully a hint of things to come.

    1. Apple hates DRM on music, but they seem quite fine with it on video.

      Their problems with Apple Records and connections to Disney/Pixar are, I’m sure, coincidental.

    2. >As to DRM it’s always worded that it’s Apple’s fault for supporting it, despite that fact that Apple publicly and famously called for DRM to be abandoned

      Yet Apple continues to make it a PITA to transfer non-DRM tracks from ipod to PC.

  6. iTunes’ issues have nothing to do with DRM. They have to do with it being a Carbon-based media player/organizer/CD ripper/burner/storefront/podcasts/iTunes U/video hub/syncing platform/document management/etc. It’s grown far too much, with too little factoring and rewrite. The codebase is over a decade old and has been showing its age for a long, long time. And it’s built on QuickTime 7, which traces its design back about 20 years. It’s just a huge morass of very old, very crusty code, and I’ll wager heavily that it takes advantage of few to none of Apple’s shiny new CoreWhatever technologies. Hard to leverage any of that in an ancient cross-platform codebase.

    But again – not a damn thing to do with DRM. On that topic – people often forget that the vast majority of music in the iTunes store has no DRM whatsoever. The little that does is at the labels’ insistence, not Apple’s. Apple’s views on video DRM, however, are much less charitable, and I’ve always felt it’s been influenced by Jobs ties to Disney/Pixar.

  7. As much as I love my now 11 year old mac environment … i truly miss WinAmp …

    iTunes defies any logic … drag a folder of an album in, and there is no explainable reason why the tracks show up in the order they do … it is not alphabetical nor by date …

    and the fact that I can ‘sync’ my phone with only one computer … makes traveling with my lighter macbook air not easier … I see a great new app … hook up the iPhone ‘oh, you wanna delete everything and start new?’ … sucks …

    1. Click the checkbox for “Manually manage music and videos” in iTunes when a phone is plugged in and iTunes will stop trying to delete everything on your iPod/iPhone just because you want to upload a new video from a second computer.

    2. 1) Why can’t you delete a (non-pocast) MP3 from the iPod itself?

      2) Why can’t you drag’n’drop an archive file full of media onto iTunes (for Windows)?

      3) Why does a 64GB (easily 10,000 songs) iPod use a flat directory system? Why can’t I set up folders and subfolders?

      4a) Why doesn’t the iTunes for Windows installer add a “Send to the iPod” link in the SendTo folder?

      4b) Why doesn’t the “Automatically Add to iTunes” folder (created by the iTunes installer) work?

      5) Why can’t I still not find a backup copy of my iPod’s MP3s on my HDD, in plaintext? (Why isn’t this the default setting?)

      6) Why does the iTunes for Windows interface suck so much that it’s easier to find software using the iPod itself, rather than via iTunes for Windows? (I don’t have a Mac verson, YMMV.)

      7) Why don’t error message of the ilk: “I can’t do that, because your unfindable-without-googling-it iTunes setting isn’t set to X” have a button that says “Click here to go to the menu in question”? Or even an explanation of where to find it?

      Me, I’m not impressed by this much vaunted ‘ease to use’ platform. If I don’t fit Apple’s corporate model of what a user is and what a user does, I’m screwed.

    3. iTunes defies any logic … drag a folder of an album in, and there is no explainable reason why the tracks show up in the order they do … it is not alphabetical nor by date …

      Probably because there’s no metadata for those tracks to give iTunes the track order on that album. You can edit the metadata by selecting a track and choosing File – Get Info, right-clicking on a track and choosing Get Info, or selecting a track and hitting Cmd+I.

      If you’ve got useful metadata in place, iTunes is a great and flexible organizer. You can sort and re-sort your music however you like.

      Yes, though, iPhone/iPod syncing is annoying and clunky and stupid.

      1. All true, but to Caipirina’s point, I think it’s clear that Apple intentionally makes importing MP3s a bad experience. For example, if you wanted to rip and encode with something that gave you some control and produced decent-sounding files (like LAME), you’re likely to end up with files that contain their track numbers in their filenames, 01_title_artist.mp3, that sort of thing. If Apple really wanted to make your experience of iTunes a happy one, they’d use those to populate the track number metadata if it was absent. But that might encourage you to do Bad Things(tm), first and foremost among them being not buying your music from Apple…

        1. you’re likely to end up with files that contain their track numbers in their filenames, 01_title_artist.mp3, that sort of thing. If Apple really wanted to make your experience of iTunes a happy one, they’d use those to populate the track number metadata if it was absent.

          It would be awesome if iTunes did that kind of intelligent attempt at parsing filenames. But something like 01_title_artist.mp3 doesn’t carry the album name, so it would be track 01 of an unknown album. And even if you had something like 01_title_album_artist.mp3, the order of those different pieces of data in the filename could differ.

          I have a lot of tracks from Napster days named like this. They’re all over the place with naming schemes. Some are title_artist.mp3, some artist_title.mp3, some 01_title.mp3, title_01–artist.mp3, album_01_title.mp3, and so on — and of course spelling is really variable, since everything in the filename was typed in manually.

          I’m just not sure naming schemes are standardized enough to make a reasonable guess at parsing a filename and auto-populating metadata fields.

          iTunes copes perfectly fine when you rip from your own CDs, or import any mp3s with metadata already assigned. So I’m inclined to believe that it’s more a matter of limitations on making good guesses about metadata from mp3 filenames, rather than a nefarious plot to make you buy everything from Apple.

          Besides, can’t you set ID3 tags with LAME? If you want to rip using LAME and organize in iTunes, why not set metadata as you rip? (I know by default LAME does id3v1 tags, and iTunes does id3v2, but you can tell LAME to add id3v2 tags.)

  8. ITunes, VLC, etc. — why is it that the last decent playlist in software was Winamp 2.9x from the turn of the century?

  9. I have no issues with iTunes. Works fine for me. if you don’t want to use iTunes Apple isn’t stopping you. Multiple alternatives are a Google search away including wireless syncing. but hat wouldn’t allow people to whine about things they don’t understand and are too lazy to look into.

  10. iTunes is a great music organizer, but that’s about it. I love my iOS devices, but syncing them with a computer using a music manager is the most ridiculously backwards thing in the world.

    iTunes is proof that Apple had absolutely no clue the iPod was going to somehow turn into the iPad. If they’d had some sort of long term vision, they’d have come up with something better.

  11. Does it suck? Well maybe. But I have to remember that, ten years ago, at the dawn of the iPod age, iTunes was so much better than anything else on any plaform. Instantaneous searching really changed how I listened to music, as finding a song based on a word or two of the title or album was so much easier than navigating directories. What has changed? Well, nothing, basically, and that’s the problem. iTunes 10 is basically iTunes 1, plus all the cruft that was added to make it be an iPhone syncing tool in the meantime, which personally doesn’t make any sense.

  12. Most of itunes problems can be avoided by pirating all your movies and music.

    Not that I’m condoning torrenting a movie/mp3 in better quality than you’ll find it in the itunes store, of course.

  13. I’m going to host a web site and run Apple headlines all day. It’s bound to rake in the clicks.

    iTune is fine btw.

  14. I’ve never had an issue with iTunes. In fact, as far as music players go — I love it. I’m a stereo geek from old times, so it took some tinkering to make sure I get all of my music at the quality I want, but I’ve never had it crash or really do anything so egregious I’d want to dump it.

    I hated when Ping was released and that little Ping button showed up in my library. But I found a script that would hide it — and so it has been hidden.

    My main complaints are just that I refuse to purchase anything from the store, which is a carryover from when all of its music was DRM’d up. Now, I just think Apple is creating a stranglehold on the music industry. I’ve found that if I just want to buy music on digital formats, most labels sell directly. I’d rather they get the money than Apples.

    And that, yeah, WiFi syncing would be grand.

    I’ve yet to find anything that would make me switch. That includes Songbird. I totally would if there was something better but sometimes it just seems like complaining for complaining’s sake.

  15. Yes, iTunes is a dog of a piece of software.
    Thing is, I can’t see Apple letting you synchronize your devices without it. (Sorry songbird, et al) If you did, you would be able to by-pass the Apple store! Now that is something they will not allow.
    We are stuck with iTunes if we want an Apple mobile device.
    Here’s hoping the next version is better. (My bet is that it will have even more cruft, not less)

  16. @pinkrobot – I had to hide the Ping thing too.
    I don’t think people complain for the sake of complaining. Personally, I complain not because the software isn’t good… as you said, its fine (for the most part). I complain because I have no option as to what software I can use. What hubris to believe that they have the monopoly on software design. NO ONE can make a better music management tool?

  17. I still like iTunes over anything else. I used to LOVE Winamp when my library only consisted of 100 MP3s. Their media library didn’t really hold up against iTunes…which got me completely converted when I got my first iPod.

    But here’s some nostalgia for: Audion ( It still works in OS X!

  18. It is simple…

    iTunes is the Prison Library.

    Steve Jobs is the Warden.

    Everything going through the prison library must be approved by the warden.

    You, as the prisoner, must be watched to make sure that you do not engage in unauthorised behavior.

    Questioning authority will only result in punishment.

  19. Using an Apple product is like willfully shackling yourself to Steve Job’s whithered teat and the more of you there are, the more likely it is that someone will send terrible viruses your way. Don’t think they’re not coming. And OSX is not prepared for them. It’s soft and inexperienced. There are a million viruses for Windows because it’s widely used, but by and large, Microsoft and other companies have done a good job combating malicious software for years. And even worse is that half the Apple fanboys out there barely know how to turn on a computer. It’s a disaster waiting to happen. I’m excited to see which comes first, the viruses or the autonomous iPods that burrow into the back of your head and turn you into an iDrone.

  20. Over the years I have tried lots of music programs on OS9, OSX, Linux and Windows and I have to say that with a little research it’s easy to make iTunes your friend (and in my opinion one of the better players currently available)

    Figure out what it is that bugs you about it and download/write an script to fix it, or get an add-on application like beaTunes, senuti, TuneUp or MediaRage. There is quite a powerful scripting dictionary in there and there are very few things in the world easier to learn than AppleScript.

    iTunes can be great if you are willing to spend just a little bit of time making it work the way you want. It’s just as hackable as anything else.

    (but maybe my experience is atypical. My library is almost entirely ripped CDs and DVDs and I use Calibre/Stanza to manage my books so I never see all these appeals for cash that everyone seems to hate.)

  21. I can’t say I like iTunes or dislike it. It’s just kind of there. Not there as in so unobtrusive it melts into the background (which would be a hallmark of great design) but there as in it’s not pretty but it gets the job done, usually without too much hassle. It’s never outright prevented me from doing anything substantial. I’m sure Apple has a significant incentive to keep iTunes front and center in order to drive people to the iTunes store. I don’t really have a problem with that: I expect them to promote and favor their own products, unless and until they cross antitrust lines. I use the store to buy music because it’s convenient, but I’ve never had a problem with music purchased elsewhere either (or playing iTunes purchased music on non-Apple stuff, such as Rhythmbox on Ubuntu) so it’s not as though my content is locked to iTunes or Apple in general.

    Apart from its general ugliness and awkwardness, my only real complaints have been about some synchronization oddities. I used to be able to create a smart playlist of unplayed podcasts to transfer to and listen to on my iPhone, but that doesn’t seem to work anymore. Also, it’s awkward to try to sync a device between two different computers: I’d like to sync my calendars and contacts between my phone and work laptop and also between my phone and home desktop, which is possible, but requires some manual fiddling each time rather than just being automatic.

    Other than that, I give iTunes a solid C. Not great, but not especially deficient either. It’s down there with the Finder as one of Apple’s uglier inventions, but hardly a worst of breed example.

  22. iTunes has some annoyances. Making the iPod device file structure a big coded secret, for instance, is stupid and should be done away with, but it’s not a huge deal. Workarounds abound. Brooker’s big gripe is with the method of “syncing” a definable list of stuff between your computer and device, vs. interfacing with the device like you would with a big Windows XP flash drive.

    For me, the syncing method is preferable, but I have a big music library, lots of podcasts and several devices. Getting all my stuff on and off the device with just a Windows/Mac Finder interface would be impractical.

    The inability to drag and drop is a bit of an annoyance, but probably not worth an editorial in The Guardian.

  23. There is surely nothing more douchey in this world than the real MAC fanboys.

    Macs are nice looking. They are built, in general, very well. The operating system is reliable.

    I have a friend and at least one relative that I have to hear it form every single time any discussion of computers arises.

    “When are you going to switch the superior system?”.

    This is coming from people who read their mail, browse the web, and watch some videos. Some of us (myself included) are tinkerers. We aren’t a small group. We’ve existed since the dawn of time.

    Leave me the fuck alone with your bullshit nonsense. If I wanted to get reamed for over 2500 dollars for a fucking computer, I’d go and do it.

    Steve Jobs is a massive prick too. Fuck him.

    1. I fail to see your point.

      You can do all the tinkering you can do one Linux or Window 7 on Mac OS X.

      Linux is a little closer, of course, being an UNIX-like OS, but it has a still easily the worst interface of the three.

  24. “embraced the truth

    Ha, that’s a good one Rob! Spoken like someone who has made it to the second-last stage of the Windows-to-Mac transition: Unjustifiable smugness and feelings of superiority.

    The last stage is realising a computer is a computer and that any machine’s usefulness is likely to be reflected by the price paid for it.

    Not including the design factor (for which Apple is unarguably a leader) isn’t it still the case that dollar for dollar you can buy more speed/memory/power in a PC than a Mac? I have extensively used both platforms and IMO there is not a great deal of increased efficiency when comparing OSX to Windoze. Efficiency has more to do with the operator’s understanding of how to best use a machine and their capacity to remember all the damn key commands (And thanks to Mac vs. Win now I have TWO sets of key commands to remember).

  25. Boy, I do not understand the ITunes hate I see all over here and over at Ask Metafilter.

    For one thing, I think the “sync these playlists to my phone” model is awesome compared to dragging and dropping and mounting the ipod as a disk or some such. I’ve got my iphone set to sync to a playlist that is “Everything is this other playlist that’s rated higher than 1 star”. While I’m listening to music on the iphone, if a song I decide I’m sick of comes on, I rate it one star and the next time I plug it in to the computer that song just goes away without my having to go find it and drag it to the trash or something. For me, that right there sells it.

    Now, if you’ll excuse me I guess I have to go suck Steve Jobs’ withered teat.

  26. I dragged myself kicking and screaming into the OSX world because I was sick of viruses, and I love having a real terminal, proper sleep/wake and stability.
    Other than the contemptible Finder (which over a year later I’ve now made just about acceptable with TotalFinder), iTunes was the one thing that I would absolutely never accept having to use.

    So I am literally running Windows non-steop in VMware Fusion in order to continue to use the awesome foobar2000, which is basically the anti-iTunes, but unfortunately is (and will always be) Windows-only.
    That’s the main trouble for the Mac switcher – iTunes is awful on any platform (worse, even, on Windows), but there are alternatives. There are no reasonable alternatives on OSX, Amarok notwithstanding (Songbird is your standard Mac “alternative” – looks and feels exactly the same, what’s the point?)

    On my computer, the execrable iTunes has been replaced with a script which stops it running – ever. No accidental clicks of the “Play” button will allow it run. I switch the script out if I absolutely need it to back up or upgrade my iPhone, but otherwise I have it eradicated.

    Ah, I love a good rant. Thanks, BoingBoing!

  27. the best part about itunes is when you update the phones software and it erases all your contacts, all your apps, everything and then you can’t restore back to a point when you did have them.

    P.S itunes sucks, Apple sucks. the easiest solution stay away from Macs altogether.

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