The Herd with Colin Cowherd
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Sharp or Square - Underrated Gambling Movies with Michael Lasker
In this episode of Sharper or Square, hosts Chad Millman and Simon Hunter invite Hollywood insider Michael Lasker to explore the world of cinema, focusing specifically on underrated gambling movies and the shifting landscape of film production. The discussion moves away from sports betting to examine how modern studios—specifically A24—are reviving the mid-budget adult drama, a category that many feared had disappeared due to the prevalence of major superhero franchises and streaming content. Lasker provides insight into the "Christmas corridor" in Hollywood and explains why theaters remain essential for communal experiences. The conversation pivots to how platforms like YouTube serve as a breeding ground for new directing talent, using films like Backrooms and Obsession as prime examples of small-budget projects achieving significant success through fresh, risky storytelling. The hosts also debate the merits of television versus film for certain narratives, noting that while some stories benefit from the long-form development of a series, others, like Obsession, work best as tight, impactful cinematic experiences. Finally, the group analyzes why traditional gambling films often focus on themes of addiction, contrasting them with the lighter, wish-fulfillment style of heist movies.
Updated Jul 3, 2026
About This Episode
What are some of the most entertaining betting and casino movies you've never seen? Today's returning guest is Hollywood talent manager Michael Lasker, who joins hosts Chad Millman and Simon Hunter for a terrific conversation covering sports betting, the rise of the mid-budget Hollywood movie, the concept of "director jail,” and more. Together the trio provide recommendations like ‘Diggstown’ and ‘Mississippi Grind,’ two films very few gamblers are familiar with today. Later, we hear about the rise of the A24 studio and any early Academy Award contenders. #Volume
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