#91: The Definitive 'Any Given Wednesday' Retrospective — A Complete Breakdown of the Worst Show in HBO History

The r/BillSimmons Podcast

Welcome to Episode 91! We bring on Scott from Twitter (@Cap_tain_Ron) to focus all of our attention this episode on Any Given Wednesday, the short-lived, Bill Simmons-hosted, 2016 HBO sports late night show. It remains an enigma to this day given how bad it was, a shocking career failure for Bill Simmons, who came into HBO at the peak of his powers. So, we break it all down. How did this happen? Why did Bill agree to host a TV show and then seemingly have zero idea of what to do? Did any of Bill's pre-show thoughts end up playing out? Just how terrible was this show? For anyone that's ever watched and wondered "how did this get on TV, and why was it so bad?" enjoy this definitive breakdown of the worst show in HBO history.

0:00-21:30: Bill's questionable "reasons" for doing the show, HBO's misleading marketing, his (lack of) gameplan, and was Any Given Wednesday doomed from the start?

21:30-39:00: Episode 1: Charles Barkley & Ben Affleck: Shockingly terrible opening monologue was a bad omen, and the viral Affleck rant hides how weak Bill was

39:00-59:15: Episode 2: Bill Hader, Mark Cuban & Malcolm Gladwell: This episode confirms Bill is awkward on TV, the show isn’t funny and Bill isn’t a performer, and it’s a worse version of Bill's podcast with weak, not fully fleshed out columns as boring video monologues

59:15-1:13:50: Episode 3: Joe Rogan, Chris Bosh, Anthony Anderson: The show is definitively not working, and this is clearly not "The Sport of Conversation" we were promised by HBO's marketing. Bill's "genre changing idea" to have on two guests to talk one topic is the worst yet with Bosh and Anderson talking NBA and TV. And why does the show look visually terrible?

1:13:50-1:23:15 Episode 4: Aaron Rodgers: One-guest episode after a Serena Williams monologue highlights just how random Any Given Wednesday has become

1:23:15-1:42:15 Episode 5: The worst episode in the series - the Deflategate sketch with Michael Rapaport. This essentially officially kills the show for good, as no show that respects itself could put that sketch on air. Also, why did Bill hire comedy writers and what did they actually do, because the show wasn't funny.

1:42:15-2:30:45: By Episode 6 the show is, for all intents and purposes, over. We continue going through each episode (all 17!) highlighting key segments, like the atrocious Nas & KD joint interview. Who was this show for? Why did Bill Simmons barely act like Bill Simmons and leave behind his Sports Guy brand? Why would people continue watching a milquetoast interview show with stale sports takes? Why is Bill having on weak guests like Jay Glazer and Vince Staples multiple times? Finally Bill's pairings start working (Al Michaels/Bob Costas), but by then it's too late.

2:30:45-2:42:36: Our takeaway: Bill liked the idea of hosting an HBO show, but never actually had a gameplan for the show. Plus, Bill's surprising honesty about why it didn't work in post-show interviews.