At the end of this interview, Dan Wakefield says ‘’I guess that’s it. That’s everything I know. That’s doubtful of course, but the amount of insider history covered in this podcast is wide ranging. One of the first practitioners of what was called “The New Journalism,” he tells stories from the great age of celebrity profiles. Wakefield covered Senator Adam Clayton Powell’s trial for tax evasion and sat in on lunches with Powell and Murray Kemption. He tells stories about William Buckley, Gay Talese, his dates with Mia Farrow, and his friendship with some of the great editors of the time, including Sam Lawrence—editor of Katherine Anne Porter, Donleavy, Jim Harrison, Frank Conroy, Vonnegut, and Wakefield himself. This great storyteller remembers conversations and places as though they took place yesterday.

In this episode, prose writer Dan Wakefield talks about the importance of poetry in his own life and in his writing. This is a wide-ranging conversation that touches on many poets, writers, and musicians: including the teacher who gave him the Carl Sandburg poem that gave him permission to leave Indiana for New York; memories from his deep friendships with poets May Swenson, Anne Sexton, and Maxine Kumin; brief encounters with Robert Frost, Richard Wilbur, George Starbuck, and Kerouac; to the importance of lyrics in pop music.

In perhaps the most personal of these podcasts, Dan discusses the time he spent in Hollywood working on the television series James at 15, a period of his life that began with an offer he couldn’t refuse and ended with the crisis he describes in Returning. Along the way, he learns the ins and outs of the television and film industry, a world he would go on to write about in his novel Selling Out.

When Wakefield first moved to Los Angeles to start a novel in Joan Didion’s basement and later on the beach in Venice, where he lived at the Chateau Marmont and entered a tumultuous relationship with Eve Babitz, former girlfriend of Jim Morrison, designer of album covers for Buffalo Springfield, and writer of essays and stories, including “Black Swans,” a story based on her relationship with Dan. In this podcast, Dan recalls this time as the “best year of his life” but says “I could never live through another one.”

Wakefield began his journalism career as a civil rights reporter for The Nation, The Atlantic, Esquire, and The New York Times. After his coverage of the Emmett Till trial, he continued being fascinated by trials. “It was like reading a novel,” he explains in this episode. He talks about the James Jones From Here to Eternity trial and the Adam Clayton Powell tax evasion trial, and he talks about Dorothy Day, Norman Mailer, and William Buckley. In 1968 he wrote a longform piece about the Vietnam War, “Supernation at War and Peace” that came out as an entire issue of the Atlantic and was reprinted as a book. That reporting took him to San Francisco, where he spent time with his old New York friends Joan Didion and John Donne. During this reporting assignment, he interviewed Dean Rusk and Hubert Humphrey.

As a young journalist, Wakefield was inspired by Hemingway’s notion that you have to face death to be a writer. “I wanted to put myself at risk,” Wakefield says in this interview, “test my courage and integrity” and so he “jumped at the first opportunity to get himself shot at.” In this episode, Wakefield talks about fishing and being shot at in the Sea of Galilee, about his time living in a kibbutz and working as a shepherd in the Negev Desert, about hitchhiking in Israel, and interviewing Golda Meier. He describes an elaborate meal in the middle of the desert with Bedouins, and eating the notes he’d made when he was in danger of being imprisoned as a spy.

Dan had the opportunity to study under some of the greatest teachers/writers/critics of the 20th century, including Lionel Trilling and Mark Van Doren. Rabbi Harold Kushner was also there. He also lived in New York at the height of the popularity of Freudian analysis. In this episode, he talks about the people he knew at Columbia, his work with C. Wright Mills, how analysis almost killed him, and about the importance of pure will in a writer’s life and work.

In 1955, Wakefield graduated from Columbia University and went looking for his first job. Through Indianapolis connections, he landed an interview with Barney Kilgore, editor of The Wall Street Journal. He wasn’t, Kilgore told him, quite ready for the Journal, but he was given a reporting job at a small paper in Princeton, New Jersey, where every day he watched Albert Einstein walk to work. The story of how he moved from the “Princeton Daily Packet” to being a reporter covering the Emmett Till trial for The Nation, is inspiring, but it’s the story of the trial itself that is the center of this podcast. The other center is his reminiscence of famed sociologist C. Wright Mills, author of The Power Elite. Both the Till trial and Mills resonate with our current political culture.

At the time of this taping, Wakefield was Kurt Vonnegut’s “oldest living friend.” It was Vonnegut who wrote the New York Times review of Wakefield’s Going All the Way and it’s Wakefield who posthumously edited Vonnegut’s stories, letters, and graduation speeches. They both grew up in Indianapolis and attended Shortridge High School. Wakefield talks about their long literary and personal friendship and gives stunning insight into Vonnegut’s life, work, and family.

When Dan Wakefield moved back to his hometown of Indianapolis in 2005, he saw it with a different lens and was re-awakened, in his 80s, to the history of racism and the erasure of Midwestern black culture that he had been blind to as a child. He brought a lifetime of his own civil rights reporting and things he hadn’t understood in long friendship with writer James Baldwin to bear on what he saw and heard, and the result is the essay “Old White Guy Gets Woke” and his comments on the racial crisis as it manifests today.