Bob Dylan’s 2008 album release was The Bootleg Series v8: Tell Tale Signs, about which more in a couple of days. To promote the release, Dylan produced a new music video for the song “Dreamin’ of You”, a song recorded during the sessions for Time Out of Mind but previously unreleased. As a song it is only fair – it wouldn’t have greatly improved that album, and it is not a great lost classic. As a video, however, I quite like it.

Ever since Dylan started making music videos in the 1980s, they have mostly sucked. Dylan’s music videos have done very little to push that medium forward, and can be pretty generic. There have been a few that have been alright (“Unbelievable”, with Molly Ringwald, isn’t terrible), but it has never seemed that Dylan cared enough to work with the kinds of filmmakers that might push him into interesting territory.

This video, which uses only archival footage of Dylan, seems to me to be a turning point. He will release two videos in 2009 (more next week, of course) both of which are good, and in 2012 he will release his best video ever. Something happens (in a nutshell: Nash Edgerton) to turn Dylan around on the whole video thing.

This video isn’t perfect, but, as I say, it is his best one up to this point in his career. It features Harry Dean Stanton almost exclusively. Stanton, who has a long association with Dylan going back to Renaldo and Clara and who performed live with him at the Chabad Telethon, is an interesting surrogate for Dylan here – you can just watch his eyes in this video and that would be enough to keep most people entertained.

The video hits the theme of the album squarely on the nose. Stanton plays a bootlegger driving through the desert (always the desert with Dylan), collecting his vinyl and his DAT tapes and checking set lists. Stanton hunts Dylan, and he catalogues him. He’s a bootlegger, and the video even throws in a shot of Great White Wonder. One really effective moment is the flashing montage of changing concert posters that record the passage of the Never Ending Tour – almost all of which is available as bootlegs.

The best moment in the video is when Stanton lip-synchs Dylan:

I’ve been dreamin’ of you

It’s all I can do

And it’s drivin’ me insane

Dylan sings the song (presumably) to a woman, but putting the words in the mouth of the bootlegger, Dylan essentially sings back to himself. It’s kind of creepy, actually, and a sly shot at the bootleggers that Dylan has always shunned.

The other great moment is Stanton stamping Bootleg Series v8 across his tape box.

Prior to this, Dylan hasn’t much cared for music videos, it seems to me, and maybe he didn’t have much say in this one either (again, he didn’t bother to show up for it). Yet this one says something – it has an actual point of view – and it seems to spark a renaissance in Dylan videos that we’ll get into next week.