Bill Simmons Podcast

Bill Simmons invented the long-form sports podcast format, and two decades in, he's still one of the best at it. The show leans Celtics, leans narrative, and leans heavily on whatever Simmons finds interesting that week — which could be an NBA trade, a 1990s deep cut, or a sprawling conversation about how the league has changed.

Not the most analytically rigorous show on this list, but Simmons' ability to contextualize the modern game against NBA history is genuinely unmatched. The mailbag episodes and the long-form guest conversations are consistently worth the runtime.