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Liberating content from an iPod

Jerry Pournelle, who I happen to believe is, in fact, the tech world's original blogger, is fond of saying that he makes mistakes so his readers don't have to. I aspire to this position, but the reality is, I make mistakes because I'm an idiot. And then when I write about it, hopefully you'll learn from my mistakes and not make them yourself. There was the time I blew away the wrong partition on my hard drive while installing Windows in 1999, thus losing years of email. There was the time my personal Web site was "hacked by the Chinese," though I was lucky enough to have coincidentally stored the actual site outside of C:\Inetpub\Wwwroot, thus saving myself from total disgrace. And a million more. Like I said: Idiot.

Anyway, I pulled another classic Paul maneuver last week when I blew away my main desktop to install the x64 version of Windows Vista Ultimate. As you might expect, I went through the process of backing up what needs to be backed up. I even remembered to de-authorize my iTunes Store and Audible accounts from the PC, which is a classic thing to forget. I thought I had done it all.

After reinstalling the system and re-applying all the applications I use, however, I discovered something disturbing. I hadn't backed up my iTunes playlists and ratings. I'll explain why this is important in a moment, but understand that I have spent far too much time than is necessary organizing my music collection. I do this because I have a problem, but that's another story. Because losing this information is bad. Really bad.

About playlists and ratings

I like iTunes but the application doesn't do some things that I think are pretty basic and necessary. For example, while you can rate individual songs (and now, in iTunes 7.4, albums), iTunes doesn't store this information in the song files, but rather in its proprietary database. This means that you can't just take a group of song files from one PC and copy them over to another, unless you're interested in losing a lot of metadata, including the aforementioned ratings, play count, and last played. I don't care so much about the latter two, but the ratings are important to me because they took a long time to create and because I use them to make smart playlists which are then fine-tuned into manual playlists, some of which are then used to create CDs for my wife's car.

Because of iTunes's unsophisticated way of dealing with ratings, MusicBridge is very valuable: This wonderful application lets me copy my song ratings from iTunes to Windows Media Player (among other things). But if you need to backup your ratings, you have to get creative. Here's what I do.

First, I create smart playlists for songs that are 1, 2, 3, 4, and 5 stars, respectively. Then, I create manual playlists (1 Star, 2 Stars, etc.). Then, I copy the songs from the smart playlists into the manual playlists, where the songs from the 1 star smart playlist would go into the 1 Star manual playlist, and so on. Then, I back up these playlists to text files that can later be imported into new iTunes installs.

And that, really, is the genius of this: After wiping out the PC, I can copy in my iTunes library (over 4000 songs, disturbingly) and then import the playlists. I go into the 1, 2, 3, 4, 5 Star playlists, select all the songs in each, and then apply the appropriate rating. Voila! My ratings are back.

On a related note, I also keep a smart playlist around called "Songs that need to be rated." When I'm on a trip, I'll often access this playlist from my iPod on a plane and rate songs as they play. I can often rate 100 or more songs on a flight, since many of these unrated songs are unrated for a reason. The idea is that I'll eventually rate almost all of the songs and then cull the 1 star songs out of the collection. Currently, I'm about 500 songs shy.


Recovering playlists (and songs and other stuff) from an iPod
I'm pretty good about backing up. The problem is, the last time I did an iTunes playlist backup was in mid-September. And since I've gone on two cross-country plane trips since then (Seattle, Phoenix), and spent much of the flights on each rating those unrated songs, my imported playlists are a bit out of date. (More than a bit. I rated over 300 songs between those two trips.) So I started investigating ways in which I could recover my playlists from the iPod classic, which I specifically haven't synced with the Vista x64-based iTunes install for this reason.

The reason I need to do this is that Apple designed iTunes so that it will completely wipe out an iPod when it first syncs. There are a few exceptions to this rule--iTunes will occasionally prompt you to transfer purchased music to iTunes first--but for the most part, if you agree to the default choice when you first plug an iPod into a PC, it's going to get wiped out. That's bad behavior in my book, and I'm sure Apple agreed to this years ago to quell fears from the record companies.

Naturally, there are dozens of iPod recovery tools out there, some free, some not. Most are based around the notion that you want to recover your music library, which is understandable, but that's not what I was looking for. I very specifically wanted something that could recover copies of my ratings playlists, since this is what was out of date on my system. But the range of recovery options out there is pretty impressive. (The trick is finding something that works for you, I guess.)

In the end I settled on a tool called iPod Liberator, which does exactly what I need. I tested the free trial version, which limits playlists to 100 entries, and it worked wonderfully so I bought it ($34.99).

I tested a few other programs including CopyTrans Suite and AnaPod (which doesn't work on Vista at all from what I can tell). But iPod Liberator seems like the best of those. That said, it'd be nice if there were a free option out there. Does anyone know of a good freeware iPod access tool that can recover songs, playlists, and ratings? This might be a good topic for Digital Media Core given the prevalence of the iPod, not just for recovery purposes, but for those who wish to move to other devices in the future.

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