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As the first performer at the Woodstock festival in 1969, Havens held the crowd for nearly three hours. Havens had been asked to continue playing because many artists scheduled to perform after him were delayed in reaching the festival location with highways at a virtual standstill. He was called back for several encores. Having run out of tunes, he improvised a song based on the old spiritual "Motherless Child" that became "Freedom". In an interview with Cliff Smith, for Music-Room, he explained:

"I'd already played every song I knew and I was stalling, asking for more guitar and mic, trying to think of something else to play – and then it just came to me…The establishment was foolish enough to give us all this freedom and we used it in every way we could."

His Woodstock appearance catapulted him into stardom and was a major turning point in his career The subsequent Woodstock movie release helped Havens reach a worldwide audience. He also appeared two weeks later at the Isle of Wight Festival in late August 1969.

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