Host Greg Iwinski sits down with Gabe Sherman to talk about Gabe's path from New York real estate journalist, to writing a book about Roger Ailes, to writing a movie about one of the most famous people on earth: Donald Trump.

Gabe Sherman is a journalist, author and screenwriter known for writing The Loudest Voice in the Room, the 2014 bestselling biography of Fox News president Roger Ailes. As a journalist his work has appeared in publications like The New York Times, The New Republic, The New York Observer and GQ. He previously served as national affairs editor at New York magazine and is currently a special correspondent for Vanity Fair and a regular contributor to NBC News and MSNBC.

Most recently, Gabe wrote the screenplay for The Apprentice, the 2024 feature that follows Donald Trump's career as a real estate businessman in New York in the 1970s and 1980s, as well as his relationship with lawyer Roy Cohn. The Apprentice was released in the US on October 11, 2024 and is now playing in theaters.

This episode of OnWriting is hosted by Greg Iwinski. Greg is an Emmy-winning comedy writer and no-award-winning performer whose writing includes LAST WEEK TONIGHT and THE LATE SHOW WITH STEPHEN COLBERT. He recently finished writing the first season of GAME THEORY WITH BOMANI JONES on HBO, and can be found on Twitter @garyjackson.

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