8. 'Time Out of Mind'
Bob Dylan took a long break from recording new material after the release of 1990's rather subpar LP Under the Red Sky. During that time, he toured at a relentless pace and released two discs of acoustic folk covers, but nothing new emerged. "I was disillusioned with the whole process of it," he told the New York Times in 1997. "I found myself spending more and more time in the studio doing less and less. There wasn't any gratification in it... It's not like we lack any songs to play onstage."
However, in late 1996, Dylan suddenly found inspiration and began penning a dark series of songs about love, loss and death. He was only 56 at the time, though many of the songs seem like the words of a man looking at his imminent death. (Dylan denies that any of the songs were personal.) He once again teamed up with producer Daniel Lanois, though this time around, the sessions weren't so smooth: they couldn't even agree on where to record the disc, let alone who should play on it or what it should sound like.
Though Dylan has repeatedly voiced dissatisfaction with the final product, fans and critics hailed it as a stunning return to form. It even won a Grammy for Album of the Year. In the years since its release, Dylan has released stripped-down versions of many of the songs, and he produced his last four albums by himself.