These days, any politically charged conversation can begin with somebody throwing out a rather jaded joke about how the world is coming to an end, to which everyone responds with pained laughter. Unsurprisingly, somewhat requisitely, Larry Wilmore’s “Black on the Air Live!” show at Marines’ Memorial Theatre on Saturday was no exception to this rule.

INFORUM at the Commonwealth Club, the organizer of the event, prides itself on fostering thought-provoking talks with leaders in tech, business and social issues — among them, Wilmore, who was joined by guest Michael Lewis, author of “The Blind Side,” “Moneyball” and “The Big Short.” They provided a night of conversation that covered everything from Steve Bannon to Japanese Buddhist basketball teams.

Wilmore’s weekly podcast “Black on the Air” explores “the issues of the week” as he interviews guests connected to politics, entertainment, culture and sports. Wilmore is no stranger to the intersection of current events and comedy, as the Saturday show once again underscored the qualities that made Wilmore so arresting as “Senior Black Correspondent” on Comedy Central’s “The Daily Show.”

Not only did Wilmore bring all of the wry commentary and dry wit that made him so funny on “The Daily Show,” but his conversation with Lewis underscored the sense of loss that came with the cancellation of “The Nightly Show with Larry Wilmore.”

Wilmore and Lewis’ conversation over the course of the night seemed to jump from point to point almost unbidden. The nominal focus of the talk was Lewis’ books, specifically how they seemed so in tune with trends in politics — Wilmore went so far as to say he felt Lewis’ books had an uncanny knack of predicting the future.

While Lewis ostensibly held his own parrying Wilmore’s sarcasm, some of the former’s jokes felt slightly out of touch at times. At one point, when discussing the relationship at the heart of his novel “Moneyball,” Lewis recalled the elevator pitch of the story being “like ‘Brokeback Mountain’ if they fucked each other’s ideas.” While a catchy, clever pitch (and no doubt primarily made to elicit the audience’s surprised laughter), the comment felt uncalled for.

One of the more juicy details of the night stemmed from stories regarding Lewis’ recent trip to Washington, D.C., during which he met with a wide range of individuals. When Lewis mentioned watching the State of the Union at Steve Bannon’s house, Wilmore and the rest of the audience reacted with an expected sense of confusion and interest.

Lewis then proceeded to share various insights regarding Bannon. It was a strange conversation — at times Lewis seemed impressed by Bannon’s shrewdness, almost arguing that the audience and Bannon might find common ground over their frustration regarding Trump. Though Lewis never excused Bannon’s actions or beliefs, he seemed to argue for a more complex view of the man. In the same conversation, however, he would talk about Bannon being “radicalized” by the 2008 financial crash, as well as mentioning how Bannon did not care if he let white supremacists into his movement.

Wilmore remained skeptical regarding Bannon’s redemptive qualities, and the conversation stumbled onto new topics. Still, the effects of the Bannon story lingered uncomfortably. In this sense, Wilmore’s conversation with Lewis seemed to fall prey to much of what is plaguing politics lately — everything, everything comes back to Trump. And no one seems to know where to go from there.

In this sense, the night recalled Wilmore’s segment on Bill Maher’s show, during which he pushed back against Milo Yiannopoulos. Yiannopoulos and Maher attempted to swerve Wilmore, but he persisted in resisting them. One wishes that Wilmore would have employed the same tenacious control over conversations when Lewis discussed Bannon.

Nevertheless, Wilmore’s presence was refreshing — his particular brand of clever commentary tinged with comedy was well-matched for the moments when Lewis seemed to veer into uncomfortable territory. Though the conversation faltered at times, Wilmore’s prowess as a host ultimately made the night memorable.