Watch Any Given Wednesday with Bill Simmons

Any Given Wednesday with Bill Simmons is a talk show that aired on HBO in 2016, with each episode running for approximately 30 minutes. The show was developed and hosted by acclaimed sports writer and commentator Bill Simmons, who brought his unique insights and perspectives to the conversation. The show featured a wide range of guests from different fields, including athletes, entertainers, and intellectuals. Some of the notable guests who appeared on the show included billionaire entrepreneur Mark Cuban and bestselling author Malcolm Gladwell.

The show had a distinct format, with Simmons opening each episode with a monologue that touched on various topics, such as recent sports events, cultural phenomena, and personal experiences. This segment served as a launching point for the discussion that followed, which varied depending on the guest's area of expertise. For example, when Cuban appeared on the show, he and Simmons talked about the NBA playoffs, the state of the music industry, and the future of technology.

One of the strengths of Any Given Wednesday was its ability to blend serious topics with lighthearted banter. While some episodes delved into weighty issues like race, politics, and gender, others were more focused on fun, such as a segment where Simmons and comedian Bill Hader ranked their favorite sports movies. This balance of substance and levity helped to keep the show engaging and dynamic.

Simmons also had a knack for steering the conversation in unexpected directions, often asking his guests off-beat questions that led to memorable moments. For example, in one episode, Gladwell recounted a story about a time when he played pickup basketball with a group of teenagers, which prompted Simmons to ask if Gladwell had ever dunked a basketball. This led to a funny exchange where Gladwell admitted that he had never dunked and joked that his vertical leap was only “four inches.”

Another notable aspect of Any Given Wednesday was its production values. The show was filmed in a sleek, modern studio that featured large screens displaying images and videos related to the topics being discussed. The music and graphics also added to the show's polished vibe.

Despite its strong start, Any Given Wednesday was canceled after just one season due to low ratings. Some critics argued that the show's format was too similar to other late-night talk shows, while others pointed to Simmons' departure from ESPN, where he had previously built a loyal following as a sports commentator. Nevertheless, the show remains a standout for its wide-ranging conversations, diverse guest list, and the unique perspective of its host.