The Time When a Bob Dylan Interview Unexpectedly Caught the FBI’s Eye

Bob Dylan has always been an artist who spoke out about injustices in the world. But you wouldn’t peg him for the subject of an FBI file. Nevertheless, Dylan did earn his very own file back in the early 60s, shortly after President Kennedy was assassinated.

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Not too long after that infamous moment in American history, Dylan gave an interview that felt oddly sympathetic towards the former President’s killer. This was enough to earn him the government’s watchful eye.

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The Bob Dylan Interview That Made The FBI Keep Him Under Close Watch

In the late 60s, Dylan earned the Tom Paine prize at the Emergency Civil Liberties Union’s annual Bill of Rights dinner. The award honored anyone who made major strides in the fight for civil liberties. Dylan, being an outspoken artist, was a natural choice.

But what should’ve been a moment to honor Dylan’s fight for truth was overshadowed by an off-color, at times frightening speech. Dylan took the time he was allotted to knock the oldness of the government. And he sympathized with one of America’s most notorious killers.

“I look down to see the people that are governing me and making my rules, and they haven’t got any hair on their heads,” Dylan said. “I get very uptight about it.”

This was just the start of Dylan’s tirade that night. It eased the audience in for what would become one of his most infamous moments. While many in the crowd might’ve agreed with Dylan on that front, they began to turn on him as he started talking about Lee Harvey Oswald.

“I have to be to be honest,” Dylan said at the time. “I just got to be, as I got to admit that the man who shot President Kennedy, Lee Oswald, I don’t know exactly where—what he thought he was doing, but I got to admit honestly that I, too, I saw some of myself in him. I don’t think it would have gone—I don’t think it could go that far. But I got to stand up and say I saw things that he felt, in me—not to go that far and shoot.”

The crowd started to boo, feeling Dylan’s comments were too egregious a statement for so soon after Kennedy’s death. This speech added fuel to the fire of Dylan’s ongoing file with the FBI. The undercover agents present that night reportedly started to think twice about the folkie.

Dylan’s FBI File

Most of Dylan’s FBI file concerned his alleged communist ties. The FBI began to see Dylan not just as an outspoken artist but as a cultural force.

“It is urged that this statement of Bob Dylan,” an FBI memo read. “Made at this meeting, be brought to the attention of all the Bureau’s contacts in the mass media field so that proper publicity will be given to Dylan, who by means of his folk singing, has the ability to have some communication with American youth. In addition, publicity of this sort will point up the type of organization the Emergency Civil Liberties Committee is to honor an individual of Dylan’s mentality.”

This wasn’t the first time the FBI had considered investigating Dylan. But his bold statement at the Bill of Rights dinner clearly sparked concern about the impact his words might have on the world.

(Photo by Luciano Viti/Getty Images)