On this week’s episode of Second Thought, Suzy Weiss sits down with screenwriter Allan Loeb—he wrote, among other films, 21, Wall Street: Money Never Sleeps, The Dilemma, and Just Go with It—for a wide-ranging, entertaining conversation about Hollywood, AI anxiety, compulsive gambling, and the strange psychology of risk.
Loeb opens up about creating imaginary friends whose net worths he obsessively tracked as a child, which developed into a gambling addiction that has checkered his adult life. He recounts losing fortunes shorting Tesla and spiraling through blackjack systems in Bahamian casinos—all while becoming a renowned Hollywood writer.
Suzy and Allan unpack the future of storytelling in the age of AI, why Hollywood may not be dying nearly as fast as everyone claims, Tom Holland’s attachment style, and why baseball is “the crystal meth of gambling.”
Then, comedian Dan Ahdoot joins the panel for a rundown of the week’s biggest culture stories—from the hantavirus panic to Billie Eilish’s new James Cameron–directed documentary, to the roast of Kevin Hart (the women took the night!).
