“Game Theory,” his HBO talk show, has pulled off the difficult feat of mixing sports and comedy with a political bite. Now he’s trying to up his game by going unscripted.You know Bomani Jones is about to say something funny, deadly serious or both when he spits out a sentence like “The question is simple” or “Let me tell you a secret” or, in this case, “Here’s the thing.”Explaining why he no longer regularly debates sports with people on television, Jones, 42, paused dramatically, his lanky frame swimming in sweatpants as he sat on the sofa of his Harlem apartment. “Don’t no one want to argue with me on television,” he said, a snap in his voice, dropping into a baritone. “Ain’t a whole lot of people going to come out a winner. As a result, I don’t come out a winner. I just come out a bully.”What’s characteristic here is the mix of swagger and self-awareness, and also how quickly he shifted angles when making a point. Jones did it again with his final thought: “You can make an argument that I should let them win now and again,” he said, before another one of those punchy setups: “I’ll be honest.” Pause. “I’m not that good at that.”Bomani Jones has been arguing with sports journalists on ESPN shows like “Around the Horn” and “Highly Questionable” for nearly two decades. “Game Theory With Bomani Jones,” entering its second season on HBO on Friday, is the first time he is sitting at his own desk alone. And while he’s got more than enough charisma and dynamism for the job, the real challenge is pulling off something that, he will be the first to tell you, almost never works: a comic show about sports.“This is something that no one has really figured out,” Jones said, adding that he included himself. Television is full of shows starring clever comedians doing topical jokes and sports journalists making smart points, but a happy marriage of these popular forms is rare.Comedy is hard, smart comedy even harder. But with sports, Jones explained, real fans won’t easily accept a comic with no credentials. “Bill Maher can be a comedian who happened to go to Cornell and be treated with the intellectual gravitas to do the show he does. Sports doesn’t work like that.”He continued, “Comedians love sports, but the ideas they have are typically the same as everybody else’s.” With “Game Theory,” his goal is to use sports to say something deeper, more probing and political. “We’re trying to make a funny show,” Jones said, “but that still has the weight and make points that advance things.”Jones in Season 1 of his HBO show “Game Theory.” The second season won’t be as scripted.HBOThis intellectual ambition distinguished the first season, particularly in his virtuosic desk pieces that were unlike anything else on television. They can remind you of the work of John Oliver, mixing long, intricate, forceful arguments with knowing jokes, and while Jones speaks gushingly about that host (whose offices are right across the hall), it’s a comparison he balks at. Jones is harder to pin down ideologically, and as he pointed out, unlike Oliver, he doesn’t do explainers. Jones aims to jump right into the issue, one his viewers already know, and make them look at it a new way.What Oliver and Jones share though is fierce intelligence and high standards on coming up with a novel perspective. “What I tell my writers is I’m always looking for the zag,” he explained to me, before clarifying that he did not mean a cheap contrarian take.This paid off at the height of crypto mania last year, when everyone from Steph Curry to Tom Brady were spokesmen for digital currency. Jones not only bluntly called it a grift, but also explained how crypto’s popularity in the sports world was tied to the decline in trust in institutions and how normalized gambling on games had become. It was an unusually assured and complicated take that appears prescient.Asked for his favorite segment, Jones pointed to the very first episode, when he commemorated the retirement of Duke’s legendary coach Mike Krzyzewski with a historical deep dive into how and why Black fans hate his teams, quipping that if they played the Ku Klux Klan, “we would have rooted for a zero-zero tie.”Jones, who went to Clark Atlanta University, a historically Black college, said that while he wanted to appeal to all viewers, he paid particular attention to, as he put it, “never boxing Black people out.” If only the white writers in his room laugh at a joke, he won’t use it. But if only the Black ones do, he’ll think about it. “What I mean for that segment of the audience is different,” he said. “When I walk down the street and am stopped, it’s ‘thank you for what you do.’ It’s far more essential there.”Jones, who called this show his dream job, talks as if he’s only now getting the hang of it. He’s supremely confident in his voice, but fitting it into a talk show is tricky. This is the first time he’s used a writing staff that includes veteran joke writers along with a small news department. But he is convinced that he’s at his best and funniest when he sounds as if he’s speaking off the top of his head. “One thing Season 1 didn’t have enough of is just me cooking,” he said.You hear this most clearly on his podcast, “The Right Time,” in which he can find all kinds of unexpected laughs just thinking aloud. Jones has the cadence of a natural comic even when the subject is serious. That’s why in Season 2, “Game Theory” tweaked the format of its topical segment, changing it from a script to bullet points to allow him to riff. “That’s his superpower,” said Stuart Miller, an executive producer of the series who worked on “The Daily Show” for 13 years.Jones’s background in economics means “he doesn’t do pure hot takes,” said Spencer Hall, a former colleague. Brian Karlsson for The New York TimesOn a recent morning in the writers’ room, Miller, home with Covid, stared at a table of staff members from a laptop. On the wall were cards mapping out the season. In the premiere, Jones commemorates LeBron James’s 20th anniversary in the N.B.A. with an argument that the player empowerment movement, which James is widely credited with leading, is a myth. A later episode will make another zag when he makes the case that the N.F.L. is more woke than you think.Jones had a firm command of the room as he ran through a segment with bullet points of big stories that week, testing out the new format. At one point, he reflected on a riff about how a kid who got into a fight with basketball star Ja Morant needed better fathering, saying, “ESPN wouldn’t let me do that. Now I’m on HBO.”In a segment on a video of Dana White, the president of the Ultimate Fighting Championship, slapping his wife, Jones adopted a skeptical voice about whether he would face any repercussions. After he finished, one of the writers suggested that the White joke needed to be set up better and offered a tweaked phrase.When he ran through it again, Jones didn’t take this specific advice but found a third way. First, he added a new joke. “Do you realize how insulting it is to get caught slapping your wife and no one is disappointed?” It got a big laugh from the writers. Then with a head of steam, he pulled the brakes. “If you want to hurt the brand,” he said very slowly, pausing after each word, “then he would have to say something bad about incels.”The day before, he met with a performance coach who mentioned the value of adjusting his pace. That informed his shift, but what mattered more was just working without a script. “Part of going to this format is that intuitively I know when to slow up and go faster,” he said. “It’s a feel thing. Once things get written, I struggle a little bit more.”Jones has two master’s degrees, including in economics, which inform his thinking (look at the title of his show). “He doesn’t do pure hot takes,” said Spencer Hall, a sportswriter, podcaster and former colleague. “That’s the economics training: He’ll say, ‘This is bad, but here’s an unexpected upside.’”When it comes to his comedic sensibility, Jones said, nothing was more influential than “Chappelle’s Show,” and explained that what he admired most was how a sketch like “Black Bush” used a simple premise (what if George W. Bush were Black?) to make layered jokes. “Dave is always coding it on many levels,” Jones said. “The joke is landing is so many different ways.”The simplicity is as important as the complexity. “If I find a basic idea that people aren’t thinking about it, that’s it,” he said. “If I need to go a long way to get there, it probably won’t work.”What makes doing political commentary about sports a balancing act is that fans watch games to escape. Jones understands this well, carefully managing the amount of humor in his arguments while trying to avoid dogmatism. “I don’t know how many interesting screeds are left,” he said, making a subtle point about how television has evolved in the last two decades. “Think of how impactful Olbermann’s screeds were in 2006,” he said of the sports broadcaster who shifted into politics. “Do it now and it doesn’t hit the same. You have to be more sophisticated.”That sophistication should not be mistaken for snobbery. Jones’s focus is not on who wins or loses games, but he doesn’t look down on anyone who cares deeply about that. “The place sports exist in people’s lives is important, and we get ourselves in trouble as high-minded commentators when we trivialize that,” he said. “No one would say music isn’t important. It’s a big part of the fabric of our lives. It matters. Sports is the same.” More