Larry Wilmore's Big Night: Late Night's Elder Statesman Steps up in Tonight's Career-Defining Role

This evening, comedian and late-night host Larry Wilmore will be delivering the featured remarks at the White House Correspondents’ Dinner. It’s an event marked by uncomfortable professional encounters and awkward journalists in formalwear; the schmoozing is secondary to the drinking, and the drinking is secondary to what has become the dinner’s primary purpose: a good old-fashioned comedy roast. Tonight, Wilmore is leading the charge, at what is also President Barack Obama’s last White House Correspondents’ Dinner in his presidency.

For the event not-so-affectionately called “nerd prom,” in this year, and during this election cycle, Wilmore is the perfect choice for the Correspondents’ Dinner main event. The comedian is no less than the elder statesman of late-night comedy, not because of age, but because of style.

To be sure, age has a little bit to do with it. At 54, Wilmore’s not significantly older than his colleagues across the field of late-night comedy. Jon Stewart, former host of “The Daily Show,” is just a year younger; Bill Maher, of HBO’s “Real Time,” is a few years older. But while Stewart is already semi-retired, and Maher is deep in the second stage of his career, Wilmore’s 15-month-old hosting gig on “The Nightly Show With Larry Wilmore” is his first time anchoring his own show. He came onto the scene already in middle age, and that does make a difference.

But mostly, Wilmore’s distinctly refined, diplomatic air comes from his style and delivery. Wilmore is almost professorial, when he sits down behind the desk of “The Nightly Show,” in the sort of office-hours intime that liberal arts undergraduates fantasize over. He’s distinctly softspoken, with a drawling, inflected delivery that is hard to translate to print. He radiates dignity. And his low-key demeanor both masks and cleverly deploys one of the sharpest and most self-aware voices in comedy today—one that is both very funny and unmistakably, unapologetically, and irrevocably black. Sitting next to our first unmistakably, unapologetically, and irrevocably black president tonight—who is also both very dignified and very funny—the two will be a perfect match.

Wilmore, when he stepped up to the chair of “The Nightly Show,” was the only black late-night host entering a pantheon of white men. With Trevor Noah and Samantha Bee, that pantheon has slightly diversified—and there too, only at the margins, in the distinctly less venerable format of half-hour cable shows. As I’ve written before, late-night television, especially on the major broadcast networks, is a special sort of viewing experience—a format that you invite not just into your home, but quite possibly into your bed, if you’re the type to fall asleep to the television. There’s a couch, tepid hijinks, and a band; it’s like going out while staying in.

As a result, late-night hosts become beloved to the audience at home because they become trusted, household figures; not just walking joke machines, but a frequent friend over for a drink after dinner. But trust and safety and, more saliently, respectability—especially in the context of culture being transmitted from a box in your house—are incredibly politicized concepts, steeped in their own sad history of alienation and marginalization. American race and gender relations being what they are, it has been difficult for any host that isn’t a white man to fit into the vaunted role of late-night host.

And yet, in that span of just over a year, Wilmore has made himself an indispensable part of the late-night television landscape. He was already a behind-the-scenes veteran, writing for shows like “In Living Color” and “Sister, Sister” before showrunning “The Bernie Mac Show,” for which he won a writing Emmy. He was with the writers of “Black-ish,” on ABC, for the first half of the first season before decamping to “The Nightly Show.” And for years, he was an intermittent guest on Stewart’s “Daily Show,” with the title “Senior Black Correspondent.” When he came onto the scene as “The Nightly Show”’s founding host, he was an already polished comedic personality—and far more Jon Stewart’s heir than any of “The Daily Show”’s other brilliant offspring, whether that’s Samantha Bee on TBS’ “Full Frontal” or John Oliver on HBO’s “Last Week Tonight.” Bee and Oliver come to their posts via the sharp and angled hectoring of the correspondent; Wilmore, like Stewart, is the professorial voice of reason at the center of a maelstrom.

The difference is, of course, that he’s black—and that he talks about it with fascinating, playful rigor. Wilmore’s ongoing coverage of President Obama’s last term in office is “Blacklash 2016: The Unblackening,” an ongoing series examining (and usually eviscerating) the presidential candidates’ attempts to run against Obama’s policies. In segments like this one, Wilmore winds through the sludge, breaking apart exactly why it’s extremely problematic that Governor Jeb Bush would keep assuming that black people want “free stuff.” He is patient, even-tempered, and jovial. He ends on a note of solemn disappointment—not without frustration or irritation, but markedly restrained, especially for the subject at hand.

And this is, to my mind, emblematic of Wilmore’s strategy. It is really hard to talk about racism without becoming angry. Racism is responsible for unjust incarceration and murder, at the barest minimum; it has been, throughout history, responsible for much more. It is even more difficult to experience racism without being subject to a whole host of emotional traumas. It’s a minefield of a topic, both politically and interpersonally. And as we have experienced time and time again, through any number of comedic vehicles, it is particularly fraught when comedy seeks to make light of something that is not light at all for some audience members.

Furthermore, as a black man, Wilmore has to contend with not just difficult subject matter but also the historically fraught role of black men in American public perception—whether that is as “unnamed perp #2” on a cop show, Mike Brown standing in the middle of the street, or even our own current president showing rare moments of frustration or anger. A black man talking about racism is not a popular figure in this country’s history. Neither is a black man that doesn’t fit the model we’ve come to expect of “niche” performers. Wilmore told Stephen Colbert a few months ago that he wasn’t “urban” or “ghetto” enough to make it as a stand-up comedian when he first started his career.

Wilmore’s comedic persona is both carefully calibrated to survive this minefield and subversive enough to comment upon it; he is the image of respectability, but nowhere near compliant. He’s code-switching, but for what feels like his own intriguing purposes. Wilmore’s generally unassuming personality is belied by an ease for moving between different, fluidly defined personas. An aside of his during a segment might invoke a belligerent porch-sitting commentator; another might call back to his self-proclaimed “blerd” identity. A gesture could either call to a feminine expression of disdain or a macho attempt to posture. Wilmore is intrigued by identity, and knows how to play different types. On his show, he lets other actors and performers add to that array of identities, too—notably Grace Parra, Ricky Velez, and Robin Thede. “The Nightly Show” ends each episode with a panel, and the inclusive cacophony of voices is fitting for the show, even if it doesn’t always get enough time to really take off.

The effect is to make race in America—and most brilliantly, the black experience—more than just the frequent media or political narrative of bloc voting and subcultural stereotypes. Just in Wilmore’s delivery, blackness has many guises and types; across the show, the black American experience is nuanced, historic, intelligent, and rich—as well as being puerile, crass, and full-throated, when necessary. In the midst of a conversation that can (and often should be!) weighty, heavy, and consequential, “The Nightly Show” is playful, leavening force.

The result, for the viewer, are opportunities that could not arise with most other comedian-journalists today. For example, this diner interview in Baltimore is a kind of masterpiece; the on-location segment is between Wilmore and a half-dozen gang members who declared a truce in the aftermath of Freddie Gray’s death while in police custody. It showcases Wilmore at his poised finest, but like so much of his work, it’s breathtaking for how it showcases a multiplicity of typically silent black voices. It’s not just that Wilmore is a good black comedian, per se. It’s that his work makes the term “black” feel both broader and not encompassing enough; that his comedy adds dimension and pluralism to a hierarchy that in its simplest form has been nothing but a tool of oppression.

And that work will continue tonight. Because in addition to his own softspoken, devastating humor and his broader sense of mission, Larry Wilmore will be another black man up on that dais, adding another black experience to those already showcased at the high table. It seems very fitting to me that Wilmore is speaking at Obama’s last Correspondents’ Dinner; even though the future is a bit uncertain, for both the presidency and “The Nightly Show,” that idea of bringing complexity to an experience defined by discrimination will live on for one night more.