Apple doesn’t want you taking music off your iPod and putting it onto a computer, because they’re worried about unauthorized trading. But if your hard drive crashes and take your entire music collection, being blocked from shifting your iPod contents back onto your new laptop is going to be infuriating. Fortunately, there are ways.

The Do-It-Yourself Windows Solution

If you’re trying to get your music onto a Windows machine, it’s not so hard. Windows thinks of your iPod as a simple storage device, and if you know how to find the files, you can grab them as easily as you’d pull them off a thumb drive.

For step-by-step instructions, check out Method One in this easy-to-digest article. That 2007 article is a little outdated — it goes on to suggest several software programs that are no longer available — but its instructions for getting into your iPod’s hidden music folder (where everything will look like alphabet soup) are still good. Depending on your version of Windows, finding the hidden files might be slightly different process (in Windows 7: After clicking on the iPod under My Computer, click on Folder Options, and under the View tab, select “Show hidden files, folders, and drives.”)

But pay attention to that initial step about not having your iTunes set to automatically sync your iPod, or the first thing you do will be to wipe your iPod clean. The writer here had only tested the technique with music files, which works fine (although you lose the metadata). I haven’t tested it yet with videos and other media.

This video also outlines how to browse – and transfer from – your iPod as if it were just another hard drive:

If you’re looking to get the iPod content onto a Mac, you’ll need a software program that will do it for you.

Free Software Solutions

If you want a program that will transfer music from iPod to PC without you having to do the backdoor work yourself, Sharepod comes pretty highly recommended. Download.com gives it a glowing review, and the program promises to grab songs, pictures, videos and other content, as well as your playlists, album art and ratings, from your iPod (or iPhone) and pull them to your PC.

Floola is a freeware program that offers to do a lot of things besides copy music off your iPod, from copying YouTube videos to synchronizing with your Google Calendar. Comments I’ve seen are strongly positive but, like any free program, slightly mixed. Check out reviews at Download.com and Lifehacker for starters.

If music is your only problem, FreeSync for Mac will readily move the files. If you’ve got video, photos, etc., the maker will want you to pay for the more robust version (see below).

Another free solution is iPod Folder, which works for both PCs and Macs. The drawback: Not only does it not do video, it only handles MP3 files, so if you’ve purchased music from the iTunes store, or ripped your CDs into any format other than MP3, this one won’t help you.

Solutions You Can Pay For

There are a number of programs you can buy for, of course. They’ll usually start you out with a free demo that gives you a number of days and songs before you need the license. I’m limiting the scope of this quick survey to free solutions, but here are a couple of pay-to-play programs that kept popping onto my radar:

First, as I noted in my update to the original music transfer post, there’s iPod to Computer software for PC, which starts with a free trial and goes on to a $29.95 license, and iPod to Mac Transfer program, which licenses at $28. Both are available at my partner site.

Another leading contender is Senuti, which gives you 30 days or 1,000 songs free before asking $18 for a license. Here’s a full review that walks you through the process of transferring your music from iPod to Mac.

iSkySoft, whose FreeSync for Mac moves songs for free, offers to get everything off your iPod with either of two programs, SyncPod for Mac, which will run you $39, or SyncPod for Windows, whose lower price tag ($19) may be due to the greater number of free solutions for the PC user.

What Else Have You Got?

I won’t get around to actually experimenting with these programs and techniques until either the book hits the shelves or a hard drive failure wipes out my iTunes library, but until that great or disastrous day, this post should get you started. If you’ve used any of these programs or techniques, or have a different or better solution, comment away!

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• If you are a Windows user and don’t want to go through all of this hacking, you can buy iTunes Transfer software at my partner site. It will help you back up your library – with playlists – and transfer it to your other computer.
• If you’re trying to transfer music from your iPod to your computer, unfortunately, Apple won’t let you do this freely, but you can buy iPod to Computer software for PC (free trial download), or iPod to Computer software for Mac at my partner site that will allow you to do this.
• if you just have the hard drive of your old PC, Ben has shared with us how to make the transfer
• if you aren’t keen on messing with XML files – and play count isn’t important to you - Oden has a simple process, involving smart playlists, for retaining song ratings when you transfer your iTunes library.
• Collin has a simple way to find out those duplicate songs that you may end up with when transferring your catalog.
• Aaron devised a clever way to transfer while retaining playlists in your collection.
• If you are transferring between Macs, pbaron has a method involving FireWire mode.

[Original post]

Since I’m moving, I wanted to transfer all of my music from the iTunes library on my work computer to the iTunes library on my home computer. This is pretty simple – just transfer my music from my work computer’s iTunes library onto my Firewire Hard Drive, take it home, and transfer the music onto my home computer – but I rely on all of my song ratings, accumulated over thousands of hours of listening to iTunes while I work, to populate my iPod Shuffle with songs from the “My Top Rated Songs” Smart Playlist. I couldn’t find any information on how to transfer my iTunes music, while still retaining my song ratings, but I finally figured it out.

Move Your Music Library

Before you do this, you’ll have to first transfer the actual files to your new computer. You may choose to burn CDs, DVDs, or use a thumb drive; but using a FireWire cable is easiest for large libraries, unless you have a portable hard drive.

Move Your Metadata

Here’s a video tutorial I put together. Written instructions are below.

1. Export the source iTunes library as an XML file (File>Library>Export Library…). This will create a file that holds information about the location, song filenames, and *song rating*!
2. Replace the file paths in your XML file with the path that the songs from the source library will be in when you import them. This path may point to your FireWire Drive, a DVD you have burned, or a temporary folder on your hard drive that you have copied your music to. Just to be sure of the new path, copy one of the files from this location to your library, export your destination library, and look at the file path to that song in the resulting XML file. To actually replace the file paths, I did a Find/Change in TextWrangler but you can just use TextEdit (Edit>Find>Find…).
3. Set the preferences in iTunes in your destination library to “Copy files to iTunes Music folder when adding to library.” This is under “Advanced.”
4. Import your library (File>Library>Import Playlist…).
5. Delete redundant files. If you’re like me, you have some duplicate songs in your multiple libraries. This is a tedious task, but I plan to do it over time.

Of course, you can prevent all of this by being organized in the first place. I probably should have just had an iPod that I synched with my home computer and brought to work.

If you need help getting the actual files over to your new computer, this video will show you how to copy your music to your new computer using iTunes Home Sharing:

UPDATE: If you’re looking to transfer music from your iPod to your computer, I’ve put together a short guide here. I hope to improve upon it soon, but please share your findings in the comments.

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After much thought, I have devised an emotion-based rating system. Here it goes:

1-star: Melancholy

These songs are friggen’ depressing, and with no hope of recovery. I was surprised at how few of the songs in my collection really fall into this category, so maybe I need to be more liberal in my categorization. What isn’t a surprise is that most of the songs that fall into this category are either Elliott Smith or Bright Eyes songs: “Angeles” and “Lua”, respectively, for example.

2-stars: Wistful

These songs are actually more depressing to listen to than the 1-star songs because they tend to allude – through lyrics, sound, or both – to things just lost or out of reach. This category seems to be dominated by Stars, Bloc Party, and Arcade Fire: “Lover’s Spit,” “Kreuzberg,” and “Intervention” as respective examples.

3-stars: Stable

Given that most modern music is based on The Blues, these may still be a little depressing, but are generally more soothing to listen to. These songs tend to mix subtle happiness and sadness for an overall “Stable” feel. This is where you start to see some Spoon and The Strokes show up: “Lines in the Suit” and “Automatic Stop,” as respective examples.

4-stars: Cool

Now we get into things that are perhaps danceable and have a generally more active feel. The spiraling bass line and breathy vocals of “Stars and Sons” by Broken Social Scene put that song in this category, and that crazy video-game sounding guitar solo in “Born Under Punches” by The Talking Heads is undeniably “Cool.” “Happy” and “joyous” songs would probably go in this category as well.

5-stars: Indestructible

These are those songs that make you want to dance, run really fast, lift heavy objects, leap tall buildings, etc.. This is where much of my hip-hop collection ends up, with N.E.R.D.’s “Brain” and Dr. Dre’s “Nuthin’ but A ‘G’ Thang” being a couple of favorites; and “Abra Cadaver” (no, not “Kadavy”) by The Hives, and Gang of Four’s “Natural’s Not In It” reppin’ other Genres. The ultimate “Indestructible” song goes – of course – to Spoon with “I Turn My Camera On.”

While there may be some criteria – or even specific characteristics of a song – that I point to to justify my ratings, _it’s music_ and thus this rating system is by no means scientific. I may even rate a song “Cool” today and later decide that it makes me feel “Indestructible” – it may depend upon my mood at the moment I rate the song. I have found the mood-based playlists this rating system yeilds to be pretty reliable. Does it work for you?

P.S. If you change computers, you’ll of course need to transfer your iTunes music library to retain all of these song ratings.

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I’m sure Apple has probably already thought of this and is working on it, but hurry up!

[4:16 PM - Title has been edited to be more descriptive]

[4:16 PM - One more thought]
Imagine the sales potential for the iTunes Music Store to know your ratings of songs, and to know what other songs are enjoyed by people who rate that song highly.

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