Barry Ritholtz interviews Jay Leno at the Newport Audrain Concourse d'Elegance, discussing Leno's early interest in comedy and cars, his comedic influences like Robert Klein and Richard Pryor, and his first car, a 1934 Ford. Leno shares how his car collection grew to 214 vehicles and how he decides which car to drive each day. They explore the artistry in car design, comparing classic and modern aesthetics, and touch on Leno's watch collection, drawing parallels between the mechanics of watches and cars. Leno recounts his financial strategy of banking his Tonight Show earnings and living off his stand-up income, his "barn find" car acquisitions, and a humorous story about reuniting a 94-year-old woman with her restored 1951 Hudson Hornet. The conversation shifts to Leno's experience interviewing President Barack Obama, his views on free speech in comedy, and the future of late-night television in the streaming era. The interview concludes with a speed round of car-related questions.
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