“The Apprentice,” a new film directed by Ali Abbasi, depicts the rise of a young Donald Trump under the wing of the notorious lawyer Roy Cohn. The film is, in many ways, an origin story for a man who has overtaken contemporary politics. On this episode of Critics at Large, Vinson Cunningham, Naomi Fry, and Alexandra Schwartz discuss the movie and other works that explore Trump’s and Cohn’s psychologies, from duelling family memoirs to documentaries. The sheer number of such texts raises the question: Why are we so interested in the backstories of people who have done wrong, and what do we stand to gain (or lose) by humanizing them? “Do we want to see our villains, our absolute villains—people who have caused much harm to the world—as weak little boys who’ve undergone trauma and have had their reasons for becoming the monsters they later turn into?” Fry asks. “Or do we not?”

Read, watch, and listen with the critics:

“The Apprentice” (2024)
“Who Could Ever Love You: A Family Memoir,” by Mary Trump
“All in the Family: The Trumps and How We Got This Way,” by Fred C. Trump III
“Where’s My Roy Cohn?” (2019)
“Roy Cohn and the Making of a Winner-Take-All America,” by Naomi Fry (The New Yorker)
“Angels in America” (2003)
“Joker” (2019)
“Wicked” (2024)
“Ratched” (2020)
“Elephant” (2003)
“Cruella” (2021)
“The Sopranos” (1991-2007)
“Mad Men” (2007-15)
The “Harry Potter” novels, by J. K. Rowling
“Paradise Lost,” by John Milton
“Be Ready When the Luck Happens,” by Ina Garten

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