I recently won an iPod. “iPod Classic 160Gb” the box read as i opened it and drooled at the fancy Apple packaging. It comes with it’s own usb cable, earplug phones, and a white piece of plastic which i have no bloody clue what it could be useful for, maybe resting the thing vertically.. which i failde to see how to support it and the manual provided to reference to. “Oh well, who cares about pieces of white plastic” i thought to myself. “Let’s see what this baby can do!”

Never having owned one and detesting to use bloatware such as iTunes i started looking for alternatives to update my iPod. Google and some friends on twitter provided me with some solutions that supposedly handle this hassle:
- iPod Linux, a firmware replacer, which seemed discontinued since 2004.
- Rockbox, a sync app which seemed to be what all the cool kids use.
- GTKPod, a sync app which seemed to be what all the linux kids use.
Ofcourse that following Murphy’s Law, none of the above solutions worked for my iPod. Because, as i soon learned, the iPod Classic 160Gb is a 6th? generation iPod (called Classic 3G on some sites, iPod 6g on others), it’s sub-labelled at Classic to distinguish it from the remaining iPod family products (nano, video, touch). It seems Apple decided to encrypt the firmware for this model, perhaps because the display allows you to play some games. Or probably because they want you to buy your music and videos through iTunes.
“Well, i don’t want to use iTunes. I already have my own way or sorting my digital media collection, and have no interest in accomodating to their imposed standards.” I claimed out loud in my empty bedroom as i waved my fist in the air and then proceeded to shrug and decide to install iTunes anyways. “I’m so gonna regret this.”
Atleast now there is no more pending software update notices popping up on my desktop anymore. Just 150megs of wasted diskspace for a media player that doesn’t allow me to play any of the media i have. So i launch the thing, check out the menus, notice they still expect me to pay or re-rip for access to music i already ripped to mp3. No thanks. Headed over to podcasts section and automatically they recognized my nationality and feeded me an eye cancer multitude of popular crap that i never wished for. Tried to find my way around their galleries for relevant stuff, but as soon as arts > music showed me artcovers of bikini tits i knew i was in trouble and should quit imediately. But i persisted desperatly trying to find a search button i could click and check if my favorite podcasts were actually present. Only took me a couple of frustrated growls to realize i should be looking for “Power Search.” Obviously. And if i knew the exact name or author i could find my podcasts. Great public service, for popular crap. One thing they did seem to be getting right though: the radio stations. They were listed, they were alot, they were decently diversed, they were free, and they even worked without much hassle.
So i tried plugging in my iPod and use iTunes to load it with some TED Talks podcasts and such. First thing i get: “you should register your iPod!” No, not really, i shouldn’t. I don’t want you to know what i listen to, when i listen to, just for “free online support” which will never work properly whenever i actually need it. I actually should tell you to sod off and not register my iPod! Sadly no such option was available, only a “Register Later.” Eventually i end up being able to sync the iPod, even if “some of the videos on your iTunes library were not copied to the iPod because they cannot be played on this iPod”, well, thank goodness i have a latest generation iPod then. Oh wait, you mean iTunes actually can’t transcode videos for my iPod despite being the only tool that can upload things to it?
So… I can’t really recommend to anyone that they should get an iPod Classic.
But if anyone who does own one, actually found a way to jailbreak it, i would sure appreciate you getting in touch and brightening my day.
P.S. Seems some folks have been working on it and share their info at freemyipod.org