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Can Jon Stewart live up to his ‘Daily Show’ legacy?

Nostalgic audiences will only get him so far.

After an almost decadelong hiatus, comedian Jon Stewart is returning to “The Daily Show.” Starting Feb. 12 and throughout the election season, he’ll host Monday nights, all the while serving as the show’s executive producer.

Can Stewart maintain his large and loyal following? Can he expand his audience beyond the liberal Gen-Xers and millennials who constituted his fan base from 1999 to 2015?

The nation’s mediascape, as well as its culture and politics, have changed radically over the past 10 years.

Even for an artist as popular and accomplished as Stewart, neither outcome is assured. The nation’s mediascape, as well as its culture and politics, have changed radically over the past 10 years. Those shifts have generated new challenges that Stewart and his team over at Comedy Central will have to creatively navigate.

It is, of course, perfectly reasonable to wager that this experienced political satirist is poised to haul in a massive audience in his second stint behind the desk. The man, after all, is a legitimate comedy pioneer. During his stewardship of “The Daily Show,” he became a master of “politainment,” a genre that is a profitable mix of art and commerce. It accrues consumer attention and advertiser dollars. Politainment also permits an entertainer not only to comment on, but also shape political discourse.

Few did it better than Stewart. His signature evening cocktail of 100-proof hard news and acidic partisan satire not only incubated talents such as Samantha Bee, Stephen Colbert, Hasan Minhaj and John Oliver, but also had global impact. Among those who have followed in his footsteps are Bassem Youssef in Egypt, Brian Tseng in Taiwan, Okey Bakassi in Nigeria and Ahmad Albasheer in Iraq, among others.

Stewart is not only a comedic innovator, but also something like a Trusted Name In Liberal America. His good work on behalf of veterans and 9/11 first responders has established him as an impassioned advocate for worthy causes. If liberals hoarded gold bullion or were reverse-mortgage curious or purchased “men’s health supplements,” Stewart could surely sell it to them.

Unlike other celebrity comics, he doesn’t tow a veritable Airbus A380-800 cargo-hold of personal baggage alongside him from gig to gig (although one might reasonably ask whether the “blind spots” that led to backstage tension at “The Daily Show” in 2011 have been addressed). He has not run afoul of #MeToo advocates. He doesn’t routinely “beef” with aggrieved minorities on X (as does his friend Dave Chappelle, who humorously dubbed Stewart a “super Jew” in his recent special). He doesn’t get “canceled” every Tuesday.

Nor will Stewart 2.0 lack for rich comic earth to frack. The election cycle is comedy gold (and also, alas, tragedy gold). All of which might suggest that “The Daily Show,” with its talented and likable host/executive producer, is headed for Emmy and critical acclaim, all while making bank.

Then again, if Stewart’s reboot sticks to his old script, it might just be sailing into a demographic squall. “Politainment” weds comedy and news reporting (and it does so in ways that I and other commentators sometimes find troubling). The audiences for both, it must be stressed, are splintering and siloing. The consequences are especially challenging for liberal comedians and liberal news journalists — two once-independent vocations that “The Daily Show” ingeniously merged.

If Stewart’s reboot sticks to his old script, it might just be sailing into a demographic squall.

Back in the aughts, liberal Jon Stewart plied his craft in a milieu in which the majority of influential comedic entertainers worked within a broad liberal consensus. Sure, the giants of the industry, be they stand-ups, showrunners, comedic actors, sketch comedians, etc., might have lit up stiff Al Gore or stiff John Kerry or inscrutable Barack Obama or insanely overqualified Hillary Clinton. But they’d probably also perform at a fundraiser for their campaigns.

Yet, flying completely under the liberal radar was a burgeoning conservative comedy scene gestating within that moment. Required reading in this regard is the groundbreaking work of Matt Sienkiewicz and Nick Marx, "That’s Not Funny: How the Right Makes Comedy Work For Them." This study cast light on a diverse, lucrative and growing “right-wing comedy complex,” decades in the making. It is still mostly unknown to liberals, even though shows like Fox’s “Gutfeld!” have outperformed more recent iterations of “The Daily Show.”

At his peak, Stewart could not be ignored by conservatives, if only because his popularity helped to frame so many national political narratives. The rise of a self-enclosed right-wing  “politainment” domain, however, suggests a new reality: Those to Stewart’s right no longer need to pay any attention to him (as Chris Wallace once did, and, memorably, Tucker Carlson).

Those to Stewart’s left might also tune him out. This vulnerability is particularly present among college students and recent graduates. As a person who works with Gen Z every day, please trust me when I say that this cohort is, um, different. No better or worse than any other generation I’ve taught — just different.

They consume art differently. They react to art — especially comedic art — differently than their “it’s just a joke, man!” forebears. Gen Z is far more skeptical of classical liberal pieties about race, gender, free speech and equality (versus equity) than is commonly understood.

The fracturing of audiences along political and generational lines does not necessarily doom Stewart. It simply means that the national, “ecumenical” audience for a famous liberal comedian, or any type of comedian strongly affiliated with a political worldview, is simply no longer there.

Stewart’s first challenge is to recapture the politainment space. That space, ironically, is now saturated with other liberal comedians, many of whom are his epigones (though some of his epigones, like Oliver, are supremely good at what they do). Once he does that, he’ll have to innovate; nostalgic audiences will only get him so far. Stewart will not just need to find creative ways of making liberal politainment attractive again — but he also has to stop preaching to the choir.