When Bill Simmons, the witty sports columnist-turned-podcast guru known for his encyclopedic knowledge and anti-PC attitude, burned all of his ESPN bridges with a profane flame of Roger Goodell derision, HBO became the obvious landing spot for America’s sports guy. It was a match made in heaven: the foul-mouthed leader of tackling the not-supposed-to-be-tackled joining the home of uncensored gold. Unfortunately, as seen with the 2011 Dream-turned-Nightmare Eagles, Jay Z and R. Kelly’s collaborative Unfinished Business and the current Rotten Tomatoes ratings of Suicide Squad, what’s perfect on paper is never immune to real-life failure. Despite some bright spots and moments of celebrity-filled potential through the show’s first six episodes, Simmons’ Any Given Wednesday is about as successful as the suspension appeals of his beloved Brady.
The on-screen awkwardness of Simmons, perhaps the show’s most distracting issue, was put on full display during the first episode’s opening monologue, an ode to the greatness of LeBron James’ performance in the 2016 NBA Finals. With a puzzled stare, Simmons’ eyes stayed curiously glued to the teleprompter like it was not the script, but instead the show’s initial, near-universally negative reviews that scrolled past his troubled line of site. Dressed casually as the hip dad who enjoys letting his son’s friends know that he has almost every song in Eminem’s discography downloaded onto his iPod, Simmons just seemed to be trying too hard.
In an interview with Simmons, Charles Barkley briefly provided some Barkley-esque entertainment, but the celebrity power of Any Given Wednesday turned into an over-the-top farce after actor and Boston native Ben Affleck went into full ignorant fan mode. As if Simmons’ constant Boston admiration weren’t enough Beantown love for one show, Affleck defended Tom Brady’s Deflategate while throwing the F-bomb around more than a fifth grader who learned the word for the first time. Ultimately, people wants to know what the human sports encyclopedia that is Simmons has to say, not that Ben Affleck thinks that “Deflategate is the ultimate bullshit fucking outrage of sports, ever.”
However, after a lackluster, moderately entertaining interview with Mark Cuban and Malcolm Gladwell in the overall eh second episode (which did include some incredible Bill Hader Schwarzenegger impressions), celebrity appearances have given Simmons’ sinking program just enough of a boost to stay afloat. On episode three, Anthony Anderson and Chris Bosh sat down with Simmons for the show’s “The Big Picture” segment, with Anderson offering a hilarious take on what exactly the Los Angeles Clippers pitch to Kevin Durant could have been: “Anthony Anderson is two rows off the floor cheering for you. That’s the pitch: America’s favorite dad is cheering for you.” In addition to having the courage to admit that he’s a Sacramento Kings fan, Green Bay Packers quarterback Aaron Rodgers offered genuine thoughts towards Simmons’ question of what the biggest obstacle is in solving the NFL’s concussion problem on episode four: “The mindset of players … players feeling comfortable self-monitoring.” It was the first time the show had really felt transparent, honest, and hard-hitting, the attributes most thought would be synonymous with Any Given Wednesday.
That level of realness, as well as Simmons’ ability to keep his guests comfortable, reached a glorious peak during the Caitlyn Jenner interview in the show’s sixth episode. After speaking on her decathlon glory days and the desire to be remembered amongst Jim Thorpe and other great American athletes that drove her, Jenner spoke powerfully on the time paparazzi took a post-tracheal shave photo of her, then Bruce, prior to Jenner openly addressing her decision to transition: “I said, ‘You know what, the easy way, go in the other room, you got a gun, let’s just end it right here.’ That’s like the easy way out, no more pain.” It’s these moments, with celebrities like Jenner bearing their trials and tribulations of real-life emotion and sincere conflict, that an HBO audience is waiting for, the type of segments not available to Simmons during his ESPN tenure. For Simmons to succeed, he needs to realize his audience is not a collective of angsty teens giddily eating up a 46-year-old man using big, bad words, but sports fans of all ages seeking the type of raw, beautifully uncensored and unlimited information absent from the cable sports world.
On an episode of The Bill Simmons Podcast just after the debut of Any Given Wednesday, Simmons offered his initial opinion of the program: “I think we have the bones of something I really like. We’ll know by episode 10 what the format is for good.” After six episodes, Any Given Wednesday still can’t seem to find a consistent skeleton out of a whole lot of bones. While it may still be early, Simmons and Any Given Wednesday are still a hometown Flutie Hail Mary away from being the first major misstep in Simmons’ success-filled career.
