Bob Dylan has spent most of his career steering clear of politics, refusing even to condemn the Vietnam War when asked about it in 1968 by Sing Out magazine. There have been some notable exceptions. He stunned many fans by praising Barack Obama in a 2008 interview, and on election night that year he went even further when he introduced his band at a show in Minnesota. "[Bassist] Tony Garnier is wearing an Obama button," Dylan said. "Tony likes to think it's a brand-new time now. An age of light. Me, I was born in 1941 – that's the year they bombed Pearl Harbor. I been livin' in a world of darkness ever since. But it looks like things are gonna change now."
He didn't say much about Bill Clinton back in the Nineties, but he did agree to perform at two Washington D.C. concerts three days before Clinton took office in January of 1993. At a concert at the Lincoln Monument Dylan played "Chimes of Freedom" for a huge crowd that included President-elect Clinton and his family. (Dylan last performed at the Lincoln Monument on the 1963 March on Washington, shortly before Martin Luther King Jr. delivered his "I Have A Dream" speech.)
Hours after performing "Chimes of Freedom," Dylan took the stage at the National Building Museum for another inaugural bash. Sharing the stage with The Band, Ronnie Hawkins, Stephen Stills and Don Johnson, Dylan sang "To Be Alone With You" and then played guitar on "Key to the Highway," "I Shall Be Released" and "Hang Up My Rock & Roll Shoes." It's the last time he performed with The Band.
Dylan's reluctance to discuss politics has lead to all sorts of theories that he's a secret conservative. An entire website is even devoted to the idea. Make of their arguments what you will, but it's worth noting that he agreed to perform at multiple Bill Clinton balls in 1993, and in 2010 he performed for Barack Obama in the White House after vociferously praising him during the campaign. (He's never shown up at events for Republican presidents.) Dylan also predicted a landslide for Obama at a Wisconsin show last night.