5) Victoria’s Secret Ad (2004): Many accused Dylan of selling out when he appeared in this TV commercial wandering through a Venetian palace while a model wearing lingerie and angel wings floated around. Others said it was a private joke, following a famous reply he gave during a combative press conference in 1965. Dylan never gave an explanation for his “selling out,” and years later continued on this path licensing a song to a Pepsi Super Bowl ad and appearing in Cadillac and iTunes commercials.
6) Modern Times (2006): The follow-up to Love and Theft confirmed that Dylan was comfortable in the suit he had found for himself. He rocked, he croaked, he crooned and he whispered in an album that sounded old and contemporary at the same time. The brilliant 8-minute closer, “Ain’t Talking,” was one of his great achievements in a decade full of them. Oh, and he got Scarlett Johansson to appear in this video:
7) I’m Not There (2007): Film director Todd Haynes attempted something even more ambitious than what Dylan himself had gone for in Masked and Anonymous: to capture “the many lives” Dylan has led. Using six different actors and six non-related plot lines to portray the songwriter, Haynes succeeded and failed in equal parts, but probably got closer to the mystery than anyone has. And he did so with Dylan’s approval.
8) The Time Radio Hour (2006-2009): Pulling yet another trick out of his circus suitcase, Dylan unveiled a midnight DJ who played his favorite records in topic-centered episodes, seasoning the mix with historical data, stories and jokes.
9) The Bootleg Series Vol. 8 (2008): This installment of his rare and unreleased recordings gave further evidence that the Aughts and part of the nineties had been an incredibly strong creative period for Dylan. The two outtakes of “Mississippi” prove true another Dylan myth: that he could have always excelled in so many other possible ways.
10) Christmas in the Heart (2009): After releasing the overlooked-yet-still-stunning Together Through Life (2009), Dylan ended the decade with another surprise—this earnest but entertaining collection of Christmas covers. If you thought a grandfather cannot be dangerous, watch this:
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