Originally published at: https://boingboing.net/2018/10/26/why-the-ipod-classic-remains-o.html
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I use mine on an iTube Amp in my home office. Nice orange glow of the tubes, silly hi-tech player, best of both worlds. 
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Unfortunately, 2001 also brought the world iTunes.
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He had until “shuffle play satori.”
Shuffle play = the pit of hell.
Here is my beloved very used iPod. I regularly get dragged by my younger coworkers for not using Spotify. (I also told these guys that I am an old because I don’t understand Snapchat which was met with howls of laughter and derision as apparently Snapchat is not cool anymore. ¯_(ツ)_/¯ )
When it dies, I don’t know what I will do. I have an Android phone, so at some point will need a replacement music player - but my main worry is about how to host podcasts as I don’t like the iPhone.
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I like shuffle play, I hear music that I haven’t heard in a long time.
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Repent, Sinner!
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I had a mp3 player who’s biggest complaint was that it was just an ipod clone. They leave out that it was a clone at a third the price and without Itunes.
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iTunes was perfectly fine in the iPod era when it was just a music app. It only really got bad in the iPhone era when Apple decided to make it the all-in-one synchronization tool.
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It still liked to reorganize/rename your music files, and turn that feature back on at updates, so you had to keep a duplicate of your files if like me you already had good organization and didn’t need Apple messing it up.
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Yeah, I bought a 2nd gen iPod, discovered iTunes hell, and promptly returned it to Best Buy for one of the less expensive clones.
I still have two 160 gb iPods in my life. One is my backup in case the primary dies. The beauty of being (largely) able to run it hands free is fantastic. I’ve never found a satisfactory replacement for iTunes - anyone have any suggestions?
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Eyes free, not hands free!
I like foobar2000. You can customize it to your heart’s content. Prebuilt mods are readily shared online. And it doesn’t spy on you, ply you with ads or demand you let it eat all your music into hidden folders and reorganize it.
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Our household has 4 iPod Classic: two of which have been modded to 512GB, one at 384Gb, and one that will be modded to 128GB when I get the SD card, all using Tarkan’s kits at www.iflash.xyz. Two are mine (the others are my wife), mirrored, and I use it every day (and alternate between Primero and Segundo monthly). I’d suggest the original author look into replacing the HD and battery (if they are 6G or later). We just love the players.
My big fear is iTunes. I have yet to use the Classic with iTunes 12, but I’m going to have to test it soon to adjust authorization of computers. I’m unaware of other software that can do what iTunes 11 does: sync with the classic, handle podcasts, and handle smart playlists (how I manage with almost 45,000 songs, all listened to in the last two years).
There are some odd limitations in the iPod Classic software: supposedly, over 65,000 songs it gets flakey (probably 65535 – 16 bit integer). It also can’t seem to handle playlists with more than 20K songs on them.
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My favorite music player takes microSD cards, just the thing to load up an audio book, and then keep track of what I’ve read and haven’t read.
Having to funnel every file transfer through Apple is not something worth paying extra for.
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Do you know if foobar2000 can sync to the Classic, can handle smart playlists, and can handle downloading of podcasts? Can it read an iTunes database?
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I still use mine in the car to listen to an Audible-books playlist (so that when one book ends, the next starts). I haven’t found a way to make an Audible playlist on anything but an iPod Classic. (And apologies for using Audible in the first place 
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When mine croaked I did the flash memory upgrade myself (have done it on two now, ancient 3rd gen and the more difficult to open 6th gen “classic”.) There are some quirks that are problematic (you need a PC to format the flash memory, and I had to load music in one small playlist at a time on the 3rd gen, but otherwise it was pretty easy.) I’ve even heard of people upgrading to 500gb or more of memory so they can load in lossless files. The upgrades have some memory limits depending on the model but you never have to worry about the drive going bad, and the battery will last much longer on a charge.
I for one will never use Pandora or Spotify, for assorted reasons, but mainly because with more than a month of music on my ipod I don’t have to.
I have one like this too (Lexar branded thing) that is convenient, and super cheap. It has its uses (good to keep around for emergencies like blocking out annoying chatter.)
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It’s been a long time since I had that Classic for less than a month, but I believe it only syncs with iTunes.
It can create and manage a number of playlist file extensions include its own native .fpl playlists.
There’s a plugin, but it’s seven years since the last update. It should still work with the current version of foobar2000. You can find it here, and hydrogen audio is in general a useful resource.
It can read and index any folder you point it at, but as far as I know, iTunes hides its own folders, so you’ll have to drag the files to a new folder for any other program (including foobar2000) to make use of them.
https://www.reddit.com/r/foobar2000/comments/4s41rb/moving_itunes_library_to_foobar2000/
