10. Empire Burlesque (1985): A major narrative thread of Dylan's career through the early to mid '80s was his label's peculiar and particularly ill-judged obsession to give the man a more "contemporary" sound. Dylan himself seemed to recognize this was fundamentally not a good idea, and resisted or at least complained about it, but as an aging rock star with fading commercial prospects, he acceded to a number of collaborations with label-approved producers in order to make him sound more like Johnny Cougar or Huey Lewis, or something. The nadir of these mismatches came on 1985's Empire Burlesque -- a release helmed by Arthur Baker. Baker was a minted industry hand whose resume included mixing and recording work with New Order and Cyndi Lauper, amongst others. The sessions went on interminably, and one imagines Dylan, who famously prefers to cut things quickly and with great spontaneity, growing gradually more insane. In fairness, one also imagines Arthur Baker going insane as well, tasked with forcing a cranky legend into making a "contemporary" sounding record over his objections. Anyway: The thing sounds insane, completely mad. But through the dense layers of '80s production touches and weird "trying to find a hit" arrangements, there are a bunch of pretty great songs. "Dark Eyes" is one of his loveliest ballads, and remains a fan favorite, even in this iteration. "When The Night Comes Falling From The Sky" is an ambitious and powerful piece of writing, recorded to much better effect on a version backed by the E Street Band which was later released on The Bootleg Series Vol. 1. Empire Burlesque can be a lot of fun, in its way, as an exercise of imagining what this might have been like had it been recorded during the era of what Dylan nostalgically refers to as "live studio excitement."