As a child, his family lived in Michigan, the South Side of Chicago, Queens, New York, and Virginia.
From 1965, he lived in the same apartment in Manhattan, one once rented by critic James Agee, whom Dickerson claimed to have spiritual contact with.
[2] He graduated from Yale University in 1955, after studying with novelist and poet Robert Penn Warren and Cleanth Brooks, advocates of New Criticism.
After working a teaching job in Vermont, Dickerson read his poems at venues with Beatnik poets such as Gregory Corso, Diane di Prima, and Ted Joans.
He maintained long term friendships with many well-known artists, including songwriter Leonard Cohen, actor Richard Widmark, playwright Arthur Miller, actor Roscoe Lee Browne, opera soprano Leontyne Price, Edna St. Vincent Millay’s sister, Norma Ellis, John Farrar, and ex-Poet Laureate Mark Strand.
Congressman Robert Steele (R- Connecticut), and Head of Press and Publications for UNRWA (the United Nations Relief and Works Agency for Palestine Refugees in the Near East) at its headquarters in Beirut, Lebanon,[2] where he experienced the Lebanese Civil War in 1975 and 1976.
Dickerson returned from Lebanon to the United States and became an actor, taking roles in the television series Hill Street Blues, as Police Commander Swanson,[1] and Detective Williams in David Lynch's film Blue Velvet (1986).
[5] He also featured in the soap opera Search for Tomorrow,[1] as well as local theater and independent films, such as Broken Giant, Ties to Rachel, and Stranger in the Kingdom.
Dickerson also guest starred on episodes of shows like Three's Company, Charlie's Angels, Little House On The Prairie, L.A. Law, and Sledge Hammer!.