I have a strange relationship to Bootleg Series v8: Tell Tale Signs, Bob Dylan’s only release of 2008. On the one hand I think I like pretty much every single thing on it. On the other hand, I’m not sure that I like it as an album. It’s something that has been semi-vexing me all week.

The album was released in two versions – one with two CDs, and one with three. Both cover moreorless exactly the same material: 1989-2006. There are alternate versions and outtakes from four Dylan albums (Oh Mercy, World Gone Wrong, Time Out of Mind, and Modern Times) but completely ignores the albums Under the Red Sky, Good As I Been To You, and “Love and Theft” which are from the same period. So that’s a little bit strange. It also includes a couple of the singles that wound up on movie soundtracks and which I’ve written about over the past few weeks.

There is a lot of great material here, particularly alternate versions of songs from Oh Mercy and Time Out of Mind that have been Daniel Lanois-ized. The albums also have some interesting live versions that I hadn’t otherwise come across, including a version of “High Water (For Charley Patton)” from 2003 in Niagara Falls, and the AP Carter song “The Girl on the Greenbriar Shore” from France in 1992. It really is a bonanza of fine material.

So what’s my problem? As I say, I’m not even sure. One hint might be that there are three different versions of “Mississippi” here, one on each of the CDs. This strongly appeals to the completist in me, but the arrangement of the material – which jumps around a lot in time – does not. This may be a side-effect of listening to a year’s worth of material at a time, but a CD that moves from 1992 to 2002 and then back to 1992 has somehow annoyed me.

As this projects heads into its final month, I’ve started wondering how I’m going to continue to listen to Dylan. One thing that I imagine that I’m going to do is begin to curate my own playlists much more. I have dozens of them – one per year from 1962 to 2008 now (I’ll do 2009 tonight). Those aren’t that useful – there’s too much material in a lot of them. So as I move through and delete things that I don’t want, I will likely begin to group years together as well (Born Again period; mid-1980s; early-1970s; Rolling Thunder era). I can’t imagine that I’d ever have a grouping that is this broad – seventeen years. To me, this Bootleg Series release simply covers too much material – too many eras of Dylan that seem distinct to me. It seems like this album, even while it gathers great material, tends to flatten Dylan’t “comeback” era more than I would like it to. That’s likely why I don’t like it as an album.

I didn’t pay any attention to this release when it came out in 2008, and I’m sort of glad about that now that I learned that the two volume edition was priced at $18.99 and the three volume (which came with a 150 page book) cost $129.99. Holy crap! And record companies wonder why the practice of piracy took off around this time.