I wouldn’t be writing this post or have a hobby writing about sports without Bill Simmons. I read every article on Grantland for about a year and half before it was shut down in late October of 2015. The sites fate was inevitable after Simmons left ESPN and as Grantland writers left the site while publicly sharing their distain with the worldwide leader. Movies, politics, music, technology and the rest of pop culture were mixed in with the sports coverage on Grantland. Long thoughtful articles were commonplace and I would get genuinely excited when one of my favorite writers (Shea Serrano, Mark Titus, Katie Baker, Bill Barnwell, Rembert Browne, Mark Harris, Charles Pierce, Molly Lambert, John Lopez) had a new fresh post on the main page. I survived my last job because of the small internet window in the bottom left of my screen that Grantland occupied.

I also added the Bill Simmons podcast into my listening schedule several years ago as I enjoyed his long form conversations with his friends, famous guests, and sports figures. This was back when I could afford cable and a fancy DVR which I used to record every episode of the Grantland Basketball Hour. I was and still am a Bill Simmons follower.

Shortly after ESPN announced they were not going to renew Simmons’ contract, HBO signed him to a multi-year deal, was a big donor to his new site The Ringer, and published his expanding podcast network. They also gave him a weekly show that would air in a schedule similar to John Oliver and Bill Maher on the network.

Simmons’ show, Any Given Wednesday, started off awkwardly with a stiff hot take filled “build their own fucking stadiums” advertisement and a terrible name. HBO and Bill promoted the show in the months before it aired and I kept my HBO subscription after the free trial to keep up with the show.

HBO canceled the show after 17 episodes due to its abysmal ratings. I liked this show. It was clunky and had some major flaws, but I felt if it were given enough time, it would have found its groove and a more stable audience. It wasn’t entirely fair to judge the show’s ratings as it was on a Wednesday opposite major sporting events and presidential debates. But HBO pulled the plug anyway giving Any Given Wednesday one of the shortest runs in HBO history. This week I watched every episode again including the last episode that aired two days ago.

As I went through all of the episodes a second time I noticed some things. Every episode is organized in a similar way where it begins with Simmons giving a weekly update on current events and sports, a conversation with a guest (normally one guest), a segment of Simmons giving his opinion on something, and then another conversation with a another guest. In the first conversation Simmons plays “winners and losers” where he and the guest discuss who had a good week and who didn’t. The second conversation was normally called “the big picture” where the guest and Simmons have a conversation and end the segment with mailbag questions.

The setting of the show changed often in the beginning and stayed more consistent in the last 5 episodes. The chairs changed, the couch was abandoned, and only for a couple of interviews was a table or bar booth used. Simmons’ wardrobe stayed consistent being very casual sometimes with a blazer thrown over top.

On paper the show looked great. Simmons was able to land some major guest and even had a drugged out curse filled tirade from Ben Affleck that wen viral on his first episode. But something felt off. I enjoy reading and listening to Simmons on his site and in his podcast because of the long form unstructured conversation. The TV show is only 30 minutes long so he was forced to have more fragmented and contained conversations which never felt natural. With every guest that he talked too I felt either the conversation was choppy and awkward or the conversation was great but didn’t go on long enough.

Some bits on the show just didn’t work. Michael Rapaport was on the show several times playing up his persona of pro New York and anti-Boston to try to form a ribbing fun vibe between him and Simmons. It felt like he was playing a role instead of being himself, especially during the Judge Joe Brown court segment. Rapaport even used his “unfolding the loaf” joke in multiple episodes.

Simmons quickly abandoned his AGW championship belt idea that he mentioned in the first episode. The only other time he brought it up is when he awarded it to Tim Duncan after he announced his retirement.

Every segment that showed a montage of clips and pictures as Simmons gave his opinion about something, had a movie or HBO show reference. These, specifically the HBO show references, felt forced and were only there to remind the viewers that Simmons is a fan of all pop culture, not just sports.

Overall I liked this show. I wish HBO just turned Simmons podcast into a video podcast similar to Joe Rogan and offered a live and archived stream of it. The long form, unproduced conversations are Simmons’ strengths, not studio television. It will be interesting to see what role Simmons will play with HBO in the future as he still have 2 years lefts on his contact.

Below is a rundown of each episode:

Episode 1

  • Cavilers won the NBA title because of LeBron James’ great play in Game 7.
  • Conversation with Charles Barkley.
  • Steph Curry and other NBA stars are terrible at TV commercials.
  • Conversation with Ben Affleck
  • Who holds the Belt?

Episode 2

  • Steroids in sports
  • Conversation with Mark Cuban and Malcom Gladwell
  • NBA free agency – NY Knicks are terrible at signing free agents
  • Conversation with Bill Hader
  • Discusses the different levels of Game of Throne fans

Episode 3 

  • Discusses the huge contracts given out in NBA free agency
  • Conversation with Anthony Anderson and Chris Bosh
  • MMA sale segment
  • Conversation with Joe Rogan

Episode 4

  • Dominance of Serena Williams
  • Conversation with Aaron Rodger
  • Retirement of Tim Duncan

Episode 5

  • MLB hall of fame excluding steroid users
  • Conversation with Danny McBride
  • Judge Joe Brown deflategate trial
  • Conversation with Christina Hendricks and Michael K. Williams

Episode 6

  • Current event rundown
  • Conversation with J.J. Redick and Lamorne Morris
  • Bartolo Colon can get away with anything because he is fat
  • Conversation with Caitlyn Jenner

Episode 7

  • Current event rundown
  • Conversation with Rembert Browne and Ricky Williams
  • Criticism of PSL season tickets
  • Conversation with Seth Rogen
  • Weed round with Seth Rogen and Ricky Williams

Episode 8

  • Current event rundown
  • Conversation with Jon Favreau and Wesley Morris
  • How to fix the Olympics
  • Conversation with Jonah Hill

Episode 9

  • Current event rundown
  • Conversation with Jay Glazer
  • Tribute to David Ortiz
  • Conversation with DeMaurice Smith and Malcom Gladwell

Episode 10

  • Current event rundown
  • Conversation with Amy Trask and Cris Carter
  • Jeff Probst accomplishments
  • Conversation with Joseph Gordon-Levitt

Episode 11

  • Conversation with Vince Staples
  • Conversation with Kevin Durant and Nas

Episode 12

  • Conversation with Charlamagne tha God
  • Buying out college football coaches to fire them
  • Conversation with Abby Wambach

Episode 13 

  • Conversation with Michael Rapaport
  • Cubs Curse
  • Conversation with Doug Baldwin and Joel McHale

Episode 14

  • Conversation with Vince Staples
  • San Diego Convadium
  • Conversation with Bob Costas and Al Michaels

Episode 15

  • Conversation with Larry Wilmore
  • Browns continue to loss as other Cleveland teams win
  • Conversation with Bill Burr and Wayne Gretzky

Episode 16

  • Conversation with Jay Glazer
  • Top 4 remaining sports curses
  • Conversation with Paul Pierce

Episode 17

  • Conversation with Adam Corolla and Jimmy Kimmel
  • NWO paved the way for super teams
  • Continuation with Adam Corolla and Jimmy Kimmel
  • In Memoriam
Advertisements