Like Dylan McKay blowing back into town in Season 9 of 90210, Bill Simmons has returned. Last night marked the debut of Simmons’ new half-hour HBO talk show, Any Given Wednesday, less than a month after the launch of his new website the Ringer. Through its first month, the Ringer has been excellent with exciting room to grow; through its first half-hour Any Given Wednesday is a real dog’s breakfast. To put it in the terms of tonight’s NBA draft, if the Ringer is a blue-chip talent with range and heaps of upside, Any Given Wednesday is a raw and lumbering “project” that currently lacks a clear position.
Thirteen months ago, Simmons was brusquely dropped by ESPN, the sports-entertainment monolith with whom he’d spent 14 years and that had nurtured his unlikely rise to the most famous and influential sportswriter of the 21st century. Simmons’ tenure at ESPN had been marked by restless experimentation that had produced some undeniable highs (30 for 30, Grantland) as well as “House Eats.” His quixotic envelope-pushing at the Worldwide Leader was widely viewed as the cause of his departure (it certainly was by Simmons himself), and in the runup to Any Given Wednesday, the PR line around the show has been something like Sports Guy Unchained. Of course, when Simmons was at ESPN he shared a network with the likes of Skip Bayless and Stephen A. Smith, guys who make Bleacher Report look like the Bloomsbury Group. At HBO, he’s next to John Oliver, Veep, and David Simon’s latest miniseries. Simmons is an ambitious guy who’s drawn to breadth, and Any Given Wednesday hypothetically offers an opportunity to spread his wings in previously unavailable directions.
So perhaps what’s most surprising about Any Given Wednesday, at least on first impression, is how safe it is. The first show opened with an extended Simmons reflection on the meaning of the Cleveland Cavaliers’ NBA Finals victory to the career of LeBron James, an awkward scripted monologue that felt dated, redundant, and overly branded. (The segment concluded with a groan-inducing reference to Teen Wolf, one of Simmons’ favorite movies.) This transitioned into a conversation with Charles Barkley about LeBron’s place in history, which never settled in and felt a little like two guys talking alternately around and over each other. It made one wistful for the easy and far more familiar rapport between Simmons and his former colleague Jalen Rose, another charismatic ex-jock, but Rose is still an ESPN employee, which I’d imagine precludes any participation in Any Given Wednesday, at least on Rose’s end. A sports-themed TV show separated by an iron curtain from the most powerful sports television network in the world is a chilling disadvantage indeed.
But if you can’t have your pick of sports personalities, you can always just bring on … famous dudes? Any Given Wednesday’s most befuddling segment was a lengthy sit-down with Simmons’ fellow displaced Bostonian Ben Affleck. The conversation started promisingly, with Simmons politely asking Affleck why an actor who’d successfully overcome his mid-to-late-aughts ignomy as Hollywood’s premier purveyor of terrible career choices had agreed to take on the role of Bruce Wayne in Zack Snyder’s disastrous Batman v Superman: Dawn of Justice. I perked up: Hey, that’s a good question! But Simmons is a much better conversationalist than he is an actual interviewer, and when Affleck deftly sidestepped the most interesting implication of that question—i.e., “what’s it like to be in a quarter-billion dollar movie that sucks?”—Simmons affably neglected to pursue.
Instead the conversation shifted to Deflategate, and what followed next was like listening to an unhinged Good Will Hunting cosplayer screaming into his phone at radio station WEEI. “The ultimate bullshit fucking outrage of sports, ever,” declared Affleck of a controversy over the PSI of footballs, which passed for one of the segment’s more nuanced pronouncements. Affleck’s rant was an unfunny litany of F-bombs that felt stale and rehearsed, a tiresome simulacrum of First Takery and comment-section bile. As a displaced Bostonian who supports both the Patriots and profanity and who’s no stranger to milking the ol’ Deflategate cow myself, I found myself asking: Who’s the audience for this shit?
When it comes to the whole of Any Given Wednesday, that’s not a rhetorical question. In spite of all the noise, I like Bill Simmons and am rooting for him: At his best I think he’s a smart and funny writer, and despite an improving-but-still-ongoing penchant for bro-ish clumsiness I think he’s generally a force for good in the world of sports and media. (Any Given Wednesday mostly avoids offensive prattle, although a stupid quip about how Steph Curry “lost control of his wife on Twitter” should have hit the cutting-room floor right before someone set fire to the cutting room.) But one of my most nagging queries while watching Any Given Wednesday is that even if it drastically improves, what need does it fill? Simmons is a well-known admirer of the sort of late-night “appointment” television that cord-cutting has rendered increasingly irrelevant: His first foray into TV was a short-lived stint as a writer on Jimmy Kimmel Live, and he’s a passionate connoisseur of Saturday Night Live and classic Letterman. He’s also never seemed particularly natural or at ease on television, which isn’t a knock—most writers aren’t!—and even while he was still an ESPN employee he openly groused about having to do NBA Countdown.
Being a nimble and affable talker, Simmons’ long-running podcast—first the B.S. Report under ESPN’s flag, now the Bill Simmons Podcast under the Ringer’s—is wildly and deservedly popular. And herein lies the most glaring rub with Any Given Wednesday: I’m not sure why a camera is needed for any of this. From a visual standpoint the show is a mess: a bizarre set that can’t decide whether it wants to be a “man cave” or a library so instead just feels like an overpriced sports bar with some books strewn around; sports highlight sequences that are dated and rotely assembled; jokey video bits that feel closer to GIFs than fleshed-out ideas.
Perhaps this will be one of the show’s great experiments: the transformation of a persona, style, and general orientation that’s been hugely successful in the still-evolving medium of podcasting to a TV format whose glory days are behind it. Who knows what that would look like? The first step toward improvement for Any Given Wednesday is to convince us it should look like anything.