I first decided to move my collection of music from a binder full of CDs to my hard drive around 1998. I had purchased a portable CD player (think Discman) that could play a data CD full of mp3s. The original CD rippers barely let you name things more than Track-01.mp3, but I had a system where it would at least get a directory structure set up correctly containing the genre, album and artist. Having a directory mp3/Ska/ReelBigFish/TurnTheRadioOff/Track*.mp3 (that's the year, right?) was fine for what I was doing. The entire collection was put to disk. I think I even spent the big bucks to buy an 6GB hard drive for that.
At some point I spent the time to go through and modify all of the track names so they had the name of the song. I remember doing this, and it didn't take all that long if you did a couple CDs per day. I was in college, it just took away from my video game time anyway.
In 2000, I worked for Lydstrom, a company that was working in the music business (trying to sell mp3s online). They produced a set-top box that could play their own higher quality format but being an insider, I knew how to turn on mp3-mode. The part that controlled the mp3 playing didn't use the directory structure or file name to view the track name, it used the ID3 tag attached to the end of the file. If I remember correctly, it wouldn't even play the mp3 unless it had the ID3 tag.
I installed one of these set-top boxes in my car using a 12VDC-120VAC power inverter, a small TV and the remnants of a trunk CD changer. I wrote a script that crawled through my directories and added the ID3 tag to all of the tracks based on the directory structure.
Given that CDDB was coming online at this time, I thought about re-ripping my CD collection. I started down that route, but CDDB was not robust. To uniquely identify the CD, it used the length + the number of tracks. CDs, at least the punk and pop CDs that I had, typically have 10-14 tracks and are around 45-60 minutes long. Combined with the number of CDs in existence, there's lots of collisions, so I spent all my time telling the ripping software what CD it was. Plus it was going to take a long time, and now that I was working, I didn't have as much time to do things like spend 4 days straight ripping CDs.
My new system served me well for many years. It was portable, so it could move with me from computer to computer. CD ripping software became more sophisticated, CDDB became better, FreeDB became even better than that and all devices supported the .mp3 format with ID3 tags.
I stopped buying CDs after a while, as I become a curmudgeon about music. I caught myself saying to friends, "Is it me, or is most of the music coming out now really bad?" Yup, I got old. I got one or two CDs a year probably from 2002-2007, and some of those new CDs possibly came from the library.
Most of my players up until 2005ish were various no-name portables or car stereo replacements. In 2005, I got one the original iPod Shuffles when it first came out. This required me to use iTunes for the first time. I didn't like that it managed your library. I'm a curmudgeon, I know what's best, I can do it myself. I tried everything I could to avoid using iTunes, and I eventually settled on a combination of WinAmp and various plugins to load the Shuffle. This allowed me to keep all my music situated in the directory structure and keep it portable.
That lasted me up until 2008, when I got the iPhone. That took over as my audio device of choice. I had to use iTunes at this point, but it was much better on OS X than on Windows. I ran a Linux fileserver that contained all of my mp3s, and iTunes didn't need write access to the directory (unlike older versions of iTunes).
I saw other iPhones playing music and now only did they play music, they played music while showing the album covers! I was jealous. Everybody else has spent years buying music from the iTunes store and iTunes provided the album artwork with the track. 99% of my tracks didn't have any artwork, and purchasing everything again through iTunes wasn't going to happen.
My friend introduced me to a piece of software called TuneUp. It was a plug into iTunes that would scan the files and load them with the correct album artwork. iTunes is already pretty messy and slow, so I didn't want to add an additional layer. I was already using virtual machines for other unpleasant things, and this was not different. I ran Windows XP with iTunes and TuneUp. It took a lot of baby-sitting to get through my entire library, but now I get to listen to music with beautiful artwork:
TuneUp isn't something that I'd want to have running all the time though. It slows down iTunes even more, but running it once was worth it. Since it was in a VM, I just ditched the VM when it was complete.
Nowadays, I've started buying music again. I only use Amazon. They don't have as large a selection as the iTunes store, but it's in DRM-free mp3 format, and it contains the album artwork. Eventually I will probably switch to FLAC or Ogg Vorbis formats for new music, but the conversion is more work than I want to invest in something that I have that is working fine. I'm not committed to the Apple world either, as my audio files are sitting on my fileserver that can be connected to any other piece of software.
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