This past given Wednesday, time was not on Bill Simmons’ side. When the former ESPN columnist decided to devote this week’s episode of his ballyhooed HBO talk show Any Given Wednesday to two major sports topics, he couldn’t have imagined the conversation surrounding both topics changing drastically just as the episode was hitting the air.
Simmons brought in Black-ish's Anthony Anderson and NBA star Chris Bosh for a smart, energetic discussion about the results of NBA free agency, a worthy back-and-forth that completely ignored the breaking news sweeping the internet at the time. Dwyane Wade, Bosh’s friend and teammate on the Miami Heat, was choosing to leave the only professional team he’d ever known for a new deal with the Chicago Bulls. Simmons had a primetime slot and unfettered access to one of the only people on the planet who could talk about Wade’s decision with a unique perspective, and he couldn’t do anything about it: the show had been taped hours before Wade made the call.
And if that wasn’t enough, the chunks of time Simmons spent on this weekend’s UFC 200 were soured when fighter Jon Jones was yanked from the event for a possible doping violation, news that broke just an hour after Any Given Wednesday aired. Every show that tapes segments in advance in 2016 takes similar risks, but you don’t often have the chance to watch an episode slide into irrelevance in real time.
Simmons can console himself with the fact that Any Given Wednesday has already improved in leaps and bounds from its debut last month, an abject failure that was ultimately overshadowed by the breathless, frothing Ben Affleck rant that served as its centerpiece. Every inch of virtual real estate devoted to Affleck’s alarmingly shiny visage and bubbling rage over the NFL’s Deflategate scandal was space that could’ve been devoted to a show that was otherwise stilted, hacky, and devoid of rhythm. The critics tasked with covering it didn’t pull any punches: Slate deemed it "a real dog’s breakfast," and TIME’s Daniel D’Addario kicked off a sharp, ruthless pan by noting, "it’s hard to believe… Bill Simmons is the sort of figure who evokes strong emotions." There was nowhere to go but up.
"We have the bones of something I really like"
Simmons is smart and experienced enough to know Any Given Wednesday would almost certainly start on the wrong foot. He’s a devoted scholar of host-driven late night shows, and his comedic sensibilities were largely shaped by people like David Letterman; he spent a year and a half writing for Jimmy Kimmel’s show in its infancy, a period Kimmel compared to "drowning without actually being in water;" he’s built documentary series and high-quality publications from the ground up. He knows the only remedy for growing pains is patience, and that’s why he spent so much time and energy managing expectations before his show’s premiere, a strategy he recycled from Grantland’s launch half a decade earlier. ("I think we have the bones of something I really like," said Simmons on a June 24th episode of The Bill Simmons Podcast. "We’ll know by episode 10 what the format is for good. Right now, we’re gonna try some things.")
Simmons was right in at least one respect: through three episodes, Any Given Wednesday is improving at a rapid clip, and it’ll continue to improve as Simmons and his team find their footing. But I’ve also seen enough to know that Simmons’ bad luck with the UFC and Dwyane Wade is representative of a larger, more pernicious issue with the show. HBO’s aggressive promo spots would have you believe it’s the edgiest thing in sports television, but in practice, it feels more and more like a relic from the recent past.
One of the show’s chief taglines is "the sport of conversation," and to its credit, the show’s post-premiere episodes have come much closer to realizing that ideal with lively, intelligent debates. If you listen to Simmons’ popular podcast, you know he’s a capable conversationalist, and he’s nimble enough to weave multiple participants into short back-and-forths without succumbing to the extra weight. When Mark Cuban and Malcolm Gladwell joined the show’s second episode for a segment about contemporary sports ownership, Simmons stuck to light prodding and orchestration, leaving space for a mutating conversation between his two guests. His decision to turn a subsequent segment with Bill Hader into a "speed round" was similarly smart: it gave Hader — an appealing and proven presence — room to shine, and it kept the pace quick. Combine the two, and you have a show about sports and pop culture that feels surprisingly vital.
Simmons' newfound feminism isn't paying dividends
But Simmons still isn’t quite comfortable on TV, and he all-too-frequently leans on exhausted pop culture references and jokes about the celebutantes of yesteryear. (If you want to maintain your cultural relevance, it’s best to leave your cracks at Lindsay Lohan and Paris Hilton’s expenses in the mid-’00s where they belong.) In three episodes, the only place you’ll find a woman on Any Given Wednesday is at the butt of a joke: all eight of Simmons’ guests have been men. (He told The Hollywood Reporter last month that fathering a daughter had made him a feminist; if that’s true, it’s yet to pay dividends on his TV show.)
The show also lacks the topical balance that’s made Simmons’ websites — the dearly departed Grantland and its younger, faster, HBO-backed sibling, The Ringer — so well-regarded. Almost all of its segments have revolved around sports, and the few guests it’s pulled in from the entertainment world — Affleck and Hader — ended up stumbling into sports talk anyway. (Affleck only became apoplectic when asked about the New England Patriots; Hader had to talk about playing one-on-one with LeBron James as part of filming Trainwreck.) Simmons is called the Sports Guy for a reason, but his ability to jump between topics is what earned him his following (and legions of imitators).
Why does this feel so depressing? Maybe it’s because I want to believe that Simmons is smart, self-aware, and open to change. His ability to curate and moderate is what’s made his publishing ventures compelling: he’s created space for dozens of diverse, uniquely talented writers to explore their passions on huge stages, and those of us who like reading about sports and culture are going to feel the ripple effects for decades to come. He fought to tape Any Given Wednesday instead of filming it live because he understands his limitations on camera. And yet I look at his TV show — and The Ringer, which has been thriving since its first day on Medium — and I see a property that’s only starting to succeed in spite of his presence, not because of it. All of its worthwhile segments have been worthwhile precisely because Simmons ceded the spotlight. Any Given Wednesday might fulfill his promise and continue to improve right up until its very last episode, but that’s a problem you can’t easily solve.