Posted on by Matt Thomas

The Great Roast of Bill Simmons, The Podcasting GOAT

Note: Bill Simmons has many gifts, but none more enduring than his ability to take a perfectly good idea and turn it into a totalizing worldview. Chief among these is his obsession with “who gets the keys,” a concept that began as a useful shorthand for late-game NBA hierarchy and has since metastasized into a governing principle for all human activity. In Simmons’ hands, the question is no longer who closes Game 7, but who closes anything: marriages, movies, bands, revolutions, and possibly even the Enlightenment. It is a framework so elastic that it explains everything and therefore, in a quiet and almost admirable way, explains nothing. Yet Simmons returns to it again and again, like a man who has discovered fire and insists on using it to cook every meal. The result is less analysis than ritual: a familiar incantation that reassures both host and listener that control exists, that someone always has it, and that identifying that person is the highest form of understanding. Whether this is insight or compulsion is an open question, but in the meantime, Simmons has the keys—and he’s not giving them back.

I. The Obsessive With the Keys

Bill Simmons is a strange and singular figure in American media, a man whose greatest innovation may have been to take the interior monologue of a slightly obsessive sports fan and publish it wholesale, unfiltered, and then slowly convince an entire industry that this was not only acceptable but essential. He is not quite a journalist, not quite a commentator, and not quite a comedian, but rather a hybrid form: a “Sportish Guy,” as Cousin Sal once put it, who treats every game, every movie, and every stray anecdote as part of a single, ongoing argument about how the world works. Central to that argument is his enduring fixation on control, on agency, on the question he returns to again and again with the devotion of a man checking the locks before bed: who gets the keys?

It is tempting to dismiss this as a bit, and in some sense it is, but like all of Simmons’ best bits, it has metastasized into something larger and more revealing. What began as a useful shorthand for late-game NBA hierarchy—who has the ball, who takes the shot—has expanded into a general theory of human behavior. Quarterbacks have the keys. Movie characters have the keys. Entire bands, dynasties, and historical figures are evaluated based on whether they had, lost, or never quite secured the keys. That Mark Sanchez could, for a brief and inexplicable moment, be discussed in these terms tells you less about Sanchez than it does about Simmons’ commitment to the framework. He does not particularly care if the fit is perfect. The system must be applied.

This is what makes Simmons both compelling and faintly ridiculous. He is, at heart, a “who’s on my team” guy, a loyalist who rewards proximity, familiarity, and shared history, sometimes to a fault. Former colleagues have occasionally noted that he can cool on people once they leave his orbit, a tendency that reads less as malice than as a kind of emotional sorting mechanism: you are either in the ecosystem or you are not. Some, like Kevin O’Connor, speak warmly of early generosity—gifted shirts, guidance, a foothold in Los Angeles when money was tight. Others have been less charitable, and the occasional critique, including a much-circulated piece in The New York Times, has tried to frame Simmons’ blind spots, particularly around race, as more systemic. These critiques are not wholly without merit, but they often feel slightly overdetermined, flattening a personality that is better understood as idiosyncratic rather than ideological. Simmons himself tends to respond not with grand rebuttals but with motion—hiring voices like Van Lathan, insisting, plausibly, that such moves were already in progress, and continuing on as if the conversation will resolve itself over time.

There is also, undeniably, an ego in play. Simmons has built an empire—Grantland, then The Ringer—largely on the strength of his own voice, and he is not shy about asserting it. Stories persist, as they do in any media ecosystem, including the long-running rumor that he played a role in Magic Johnson’s exit from NBA Countdown, a claim Simmons has repeatedly and emphatically denied. More verifiable is the moment that effectively ended his ESPN tenure: a live broadcast of NBA Countdown in which, after a colleague spoke at length, Simmons leaned in with heavy, unmistakable sarcasm—“Oh, is it my turn to talk now?”—a line that was funny, revealing, and, in the context of corporate television, fatal. It was the voice of the columnist breaking through the format, the irrepressible instinct to comment on the comment, to seize the keys even when the structure said otherwise.

What makes Simmons unique, and worth writing about at all, is that these contradictions—generous and insular, insightful and reductive, earnest and performative—are not bugs but features. He is a weird obsessive who has turned his obsessions into a career, and in doing so has given us a language that is at once clarifying and absurd. He loves the game, he loves the conversation around the game, and above all he loves the feeling that somewhere, in any given moment, someone has the keys.

II: The Bits That Ate the Brain

If the keys are the theory, the bits are the practice. Simmons has always understood that repetition is power: say something often enough, with just enough conviction, and it graduates from joke to canon. Thus “greatest stickman,” a phrase that should have died in a driveway, becomes a legitimate category, and suddenly Burgess Meredith is being floated as an all-timer. “Sal, Sal, BM was the greatest stickman of all time. Every lady wanted a ride.” It is ridiculous, obviously, but also irresistible. The specificity disarms you. The confidence sells it. The framework expands.

This is the Simmons trick: take a private-language riff and run it until it becomes a public one. It does not matter that no one else has ever considered ranking “stickmen.” What matters is that Simmons has, and that he will return to it, again and again, until you find yourself half-convinced that you, too, should have an opinion. It is analysis as inside joke, inside joke as analysis.

III. The Ecosystem

No system survives without a supporting cast, and Simmons has assembled one of the most durable in podcasting.

There is Cousin Sal, the indispensable counterweight, quicker and often funnier, whose primary function is to puncture Simmons at exactly the right moment. The Vegas trips are their shared masterpiece: two grown men insisting, year after year, that this time they will behave differently, and then not. Simmons, improbably, claims that he only smokes in Vegas. No one believes this. The morning-after pod is the payoff—hungover, frayed, the truth leaking out in fragments. “I only had three cigarettes last night,” Simmons offers. Sal, without missing a beat goes: “Yeah, more like three lighters.” It is the kind of line that ends the discussion because it cannot be improved.

There is Joe House, lawyer by day, chaos agent by night, who turns every appearance into a small act of self-destruction. “House Eats” remains a high-water mark: an adult man consuming Chinese food until he vomits, captured and distributed as legitimate sports media content. It should not work. It works perfectly. Drunk House—slurring, swearing, denouncing Daniel Snyder with operatic intensity—is not a bug but a feature. Simmons does not rein him in; he amplifies him. The ecosystem thrives on this permissiveness.

And then there is Nephew Kyle, the quietly essential, publicly baffling producer whose qualifications are, at best, opaque. The nepotism is acknowledged, even embraced. Simmons does not pretend otherwise. He does not have to. The show goes on. The levels are sometimes off. The energy is always on.

IV. The Interviews: High Risk, High Variance

Simmons as interviewer is a study in range. At his best, he is disarming, patient, and genuinely curious, capable of extracting moments that feel both candid and consequential. His conversation with Al Michaels is a case in point: Michaels, relaxed, recounts the day of the O.J. chase, including the now-legendary call-in where a supposed eyewitness punctuates his tip with “Baba Booey.” The co-host takes it seriously. Michaels does not. “It’s a joke, dude,” he essentially says, and in that moment you see the difference between professionals. Simmons knows enough to step back and let the story land. It is radio as it should be: a master talking, a host listening.

The interview with John Skipper is another apex moment. Post-ESPN, Skipper speaks with a level of openness that borders on the shocking—cocaine use, morning routines, the normalization of behavior that would end most careers. Simmons guides rather than pushes, and the result is a “huge get,” the kind of conversation that justifies the entire enterprise.

At the other end of the spectrum sits the Denzel Washington interview, a minor classic of mismatch. Washington arrives as if for one kind of conversation; Simmons is clearly expecting another. The opening is awkward, the rhythms off. To his credit, Simmons does not retreat. He leans in, tries to find common ground, and eventually does, or at least something like it. It is not a triumph, but it is revealing: the limits of the format, the limits of the host, the persistence of the effort.

V. Homerism as Method

Simmons’ greatest cultural contribution may be the legitimization of homerism. Before him, fandom was something to be managed, disclosed, occasionally apologized for. With him, it becomes the point. He is, unapologetically, a Boston guy: the Boston Celtics are not just a team but a lineage, a narrative, a near-mythological entity anchored by figures like Larry Bird, whose legend grows incrementally with each retelling. The takes are, at times, outta control. They are also, in their way, coherent. Simmons is not pretending to objectivity. He is offering a perspective, and trusting that the audience will meet him there.

This approach extends beyond basketball. Baseball, once a central obsession—AL keeper leagues, granular analysis—fades over time, dismissed as too long, too slow, no longer aligned with the rhythms of his life or his listeners’. Basketball remains the core competency, the area where his knowledge is both deep and defensible. Everything else orbits around it.

VI. Family and Formation

The personal mythology is never far from the surface. Simmons’ father, a longtime Celtics season-ticket holder, is both character and audience, the origin point of the fandom that would become a career. The pride is evident, even when unspoken. The access—courtside seats in the 1970s—becomes part of the narrative, a credential as meaningful as any byline.

His mother, less present on the pod but frequently referenced, provides another axis: a love of movies, a different kind of cultural literacy that feeds into Simmons’ broader interests. The recurring mention of being a child of divorce functions as a kind of grounding note, a reminder that the voice, however confident, has origins in something more fragile. He seems, by most measures, to have come out fine.

VII. Drift and Discipline

As the empire grows—Grantland, then The Ringer, now under the umbrella of Spotify—Simmons changes in ways both subtle and obvious. He fades certain voices who no longer fit the evolving brand: Adam Carolla, once a regular presence, becomes less so; Michael Rapaport, similarly, drifts out of the rotation. The official reasons are varied—tone, fit, the simple passage of time—but the underlying dynamic is familiar. Simmons is, at heart, a “who’s on my team” operator. The team changes. The roster turns over.

And yet, it is hard to shake the sense that the affection remains. These are not clean breaks so much as quiet reassignments, the byproduct of a system that requires a certain level of control. Spotify money, corporate expectations, the need to maintain a particular tone—these exert their own pressure. The outta-control energy that defined earlier iterations of the pod is still there, but it is managed, channeled, occasionally held back.

VIII. The Countdown Moment

If there is a single scene that captures Simmons in miniature, it is the one that ends his ESPN tenure. On NBA Countdown, a colleague speaks at length. Simmons waits. And waits. And then, with a level of sarcasm that is both unmistakable and, in context, disastrous, he interjects: “Oh, is it my turn to talk now?” It is funny. It is honest. It is, within the rigid structure of live television, unacceptable.

He is removed not long after.

The moment endures because it reveals the core tension: Simmons the columnist versus Simmons the employee, the impulse to comment versus the requirement to conform. He cannot quite suppress the former, even when the latter demands it. He reaches for the keys, even when they are not his to take.

VIII. Conclusion

Bill Simmons is the GOAT podcaster, full stop, and it’s worth saying that clearly at the outset because we only roast the ones we love. Bill Simmons has given us an entire language—keys, stickman, Vegas nights, Sal lines, Drunk House—and if you’ve been along for the ride, those bits don’t wear out, they compound. They get funnier with time, richer with context, a kind of private shorthand that becomes, almost accidentally, a shared culture. You either hear “three lighters” and laugh immediately or you don’t, and if you don’t, there’s not much point explaining it.

This is part of what makes Simmons both beloved and, in certain circles, a little contentious. He has clearly made enemies—inside ESPN, across the broader media landscape, and occasionally among former employees—and while it’s easy to chalk this up to ego or looseness, the better read is that the looseness is largely performative. Underneath the hangout vibe, the teasing, the Nephew Kyle chaos and the Drunk House indulgence, there is a very real set of standards, and Simmons enforces them. He is, at heart, a “who’s on my team” operator, and the team matters. People drift out. Some of that isn’t pretty. Most of it, however, is consistent with how he’s always operated: loyal, selective, and ultimately in control of the room.

At the same time, there is a sense now that Simmons is, if not slowing down, then at least rounding off the sharper edges. He talks openly about retirement in a way he didn’t a decade ago, and you get the feeling that he is aware, at some level, of the limits of the bit. Will he be seventy-five, still ranking stickmen and assigning keys? It’s hard to see it. He’s a boss now, a central figure inside Spotify, with responsibilities that extend well beyond the pod. The insurgent has become the institution, and while the voice is still there, it’s necessarily more managed than it once was.

There’s also the simple fact that Simmons is no longer a writer in the way he once was, and he knows it. The old columns—the mailbags, the trade value pieces, the obsessive digressions—have given way to the pod, to conversation, to rhythm. He jokes that his fingers don’t work anymore, and like most of his best lines, it’s funny because it’s partly true. The Book of Basketball stands as the monument to that earlier phase: long, ambitious, slightly out of control in the best way, complete with the famous pyramid (Jordan at the top, Magic above Bird, a decision that still tells you everything you need to know about him). But the shift from writing to talking isn’t a decline so much as an evolution. Simmons was always more voice than text anyway. The medium finally caught up to the man.

If and when he does step back, what we lose is not just a podcast or a brand but something rarer: a genuinely original voice that bent an entire corner of the media world toward itself. Plenty of people analyze sports. Plenty of people talk about culture. Almost no one has managed to fuse the two into a single, durable, endlessly riffable system the way Simmons has. The keys, for all their absurdity, are real in that sense. He found them early, used them often, and built something that will outlast the bit itself.

And if he eventually decides to set them down, or even just hold them a little more loosely, it will mark the end of a run that, for all its contradictions, was unmistakably his.

Posted on by Matt Thomas

On Edward Said’s “On Late Style.”

Note: This piece takes up On Late Style, the posthumously published and deliberately unfinished work by Edward Said on what he, following Theodor Adorno, calls “lateness”—not serenity or resolution at the end of a career, but tension, contradiction, and a refusal to reconcile. It’s a short book that opens out into large questions, and this will be less a full treatment than an attempt to think alongside it, particularly around the strange fact that a book about unresolvedness arrives in a form that is itself, in some essential way, unresolved.

Edward Said’s On Late Style is as rich a book as an unfinished work can be.  Published posthumously, On Late Style expands on Theodor Adorno’s concept of “late works.”  Late works are works with fall toward the end of an artist’s career, but not those like The Winter’s Tale or The Tempest which “reflect a special maturity, a new spirit of reconciliation and serenity often expressed in terms of a miraculous transfiguration of common reality” (6), but those like Beethoven’s Missa Solemnis or Lampedusa’s The Leopard–works which, in Adorno’s words are “devoid of sweetness, bitter and spiny, they do not surrender themselves to mere delectation,” or, in Said’s phrasing, are “uncoopted by a higher synthesis: they do not fit any scheme, and they cannot be reconciled or resolved” (12).

Said died in September 2003, before On Late Style was completed.  In the foreward, his wife, Miriam writes of how Said was planning to get to work and get it done: “{In late August} he said to me as we were having breakfast that morning, ‘Today I will write the acknowledgments and preface to Humanism and Democratic Criticism {…} The introduction to From Oslo to Iraq and the Road Map I’ll finish by Sunday.  And next week I’ll concentrate on completing On Late Style, which will be finished by December” (vii).  He didn’t make it, and the little quote is a moving reminder that we never know how much time we have left.  But Michael Wood, who arranged the various fragments Said had written on the topic of late style into this nearly seamless finished product, says that he doesn’t believe that Said ever wanted to finish the book: “Or rather, he wanted to finish it but was waiting for a time that would perhaps never have come.  There would have been a time for this book about untimeliness, but this time was always: not quite yet” (xvi-xvii).

What does Adorno, and Said, mean by “late style,” and why would Said perhaps have not wanted to finish his work on this topic?  Again, to understand what the term means we need to understand that late style is not simply synonomous with work accomplished late in life.  Wood puts it this way, the “type of lateness {that Said was interested in} is quite different {…} from the unearthly serenity we find in the last works of Sophocles and Shakespeare.  Oedipus at Colonus, The Tempest, and The Winter Tale are late enough in their way, but they have settled their quarrel with time” (xiii).  In other words, these works are transcendent yet resigned–the author, knowing perhaps that death is coming to claim them, moves to preempt death by surrendering his grasp on reality and moving in the direction of a “higher synthesis,” and in the process attaining “a remarkable holiness and sense of resolution” (6).  Said has nothing against such works at peace with themselves and with time, but these are not his subject.  Lateness here seems to take its raison d’etre from Dylan Thomas; it rages against the dying of the light.  As Said puts it, “Late style is what happens if art does not abdicate its rights in favor of reality” (9) and is “a form of exile” (8).

But if late style finds its power in a righteous rage against resignation, senescence, and serenity, it is at the same time complicit with disintegration and ultimately with death. In other words, an artist can embrace lateness in Said’s conception of the term, but can never be quit of it. Said writes: “For Adorno, lateness is the idea of surviving beyond what is acceptable and normal; in addition, lateness includes the idea that one cannot really go beyond lateness at all, cannot transcend or lift oneself out of lateness, but can only deepen the lateness” (13). Here, we understand why it was the Said, though he worked on the idea of lateness for over a decade, was not able to finish off what at only 160 pages is still a relatively slight work–only death itself can put a period on lateness. Wood writes: “for all his deep interest in lateness {…} Said was not attracted by the idea of a late, dissolving self. {…} Said wanted to continue with the self’s making, and if we divide a life into early middle, and late periods, he was still in the middle when he died at the age of sixty-seven {…} Still a little too early, I think he would have said, for real lateness” (xviii).

Another reason why On Late Style cannot exactly be classified as a “late” work is the urbane depth of its learning and its lightness of touch. Though deeply serious, Said in On Late Style wears his learning lightly, as only a true elitist can. For the fact is that despite its topic the book is oddly comforting; I can open it to any page in the moments before sleep and feel a rush of almost narcotic satisfaction and harmony. This effect is obtained not because Said takes an oppositional stance to his topic but because the extent of his learning is so colossal that it seems to achieve “a remarkable holiness and sense of resolution” based on its own gravitational force, even though acting in opposition to Said’s own thesis.

Thus, although we have only begun to scratch the surface of what Said has to say about lateness, it is already clear that while the relation between late style and classicism must for the moment remain unresolved, On Late Style as a text is a deeply classical enterprise, and this classicism is rooted in the remarkable range and depth of Said’s mind. Wood reminds us that being in opposition need not always mean manning the barricades–and this at least sets up the question raised in an earlier post about the ability of leftism and classicism to co-exist: “It is part of the generosity of Said’s critical imagination that he sees ‘amusement’ as a form of resistance. He can do this because amusement, like pleasure and privacy, does not require reconciliation with a status quo or a dominant regime” (xiv).

So perhaps On Late Style is complete in the only way a book about lateness can be. It circles, it deepens, it resists arriving. Edward Said writes against resolution, and the book quietly enacts that refusal, never quite allowing itself the satisfaction of a final statement. There is something fitting in this. Lateness, as he and Theodor Adorno understand it, is not a stage one passes through and exits, but a condition one can only move further into. Said, still “in the middle” by his own reckoning, never closed the circle. And so the book remains open—not unfinished in the sense of lacking something, but unfinished because its subject will not permit an end.