Bob Dylan (1993)
Bill Clinton was scene bobbing a thumbs-up, as he let his chin wag to the sounds of a cowboy-hat-wearing Bob Dylan singing 1964's "Chimes of Freedom" at the America's Reunion on the Mall concert. He didn't offer any commentary, but it didn't matter so much because the Clintons gave him a dramatic applause. He performed again later that same day at another inaugural event, singing "To Be Alone With You" and playing with the Band for a final time on a trio of songs, including "Key to the Highway." Despite this performance, and some rare words praising Barack Obama in 2008, Dylan has mostly steered clear of politics.