Stewart in '99 Comedy Central

The Clinton-Lewinsky scandal was a boon to comedy, but the comedians who feasted then look gouty today: A small group of white, male millionaires — one of whom would later confess to having multiple office affairs, perhaps to distract from sexual-harassment allegations — collectively decided to call Lewinsky, then a 22-year-old intern, fat, ugly, slutty, and worse for being caught in a sexual relationship with a powerful man who should’ve known and acted better. Jon Stewart probably wasn’t a millionaire in 1999, the year he took over hosting The Daily Show from Craig Kilborn, but he was still a part of the late-night bro pack. Recounting a car accident the former intern was in, Stewart cracked, “Lewinsky was driving alone when she reached over to take something out of her purse. Though it is not known what the object was, insiders are guessing it was either an Altoid — or a turkey leg.”

That kind of lazy fat-joke would never make it to air on The Daily Show in 2015 — at least not against a woman, because there’s something innately sexist about a man mocking a woman’s weight. (Chris Christie, however, is still on notice.) Stewart deserves a salute for all that he’s accomplished in the last sixteen years, especially for revolutionizing political comedy by upping its smarts while downplaying its smarm. Stewart’s everyman approach to the news proved you could be funny and engaged without being a smug dick like Bill Maher or Dennis Miller.

But the Stewart who doesn’t get enough recognition (or scrutiny) is the one who evolved from the white, male comedian who was happy to surround himself with collaborators who looked more or less just like him to the one who found value and hilarity in diverse points of view. The years 2004-2006 were great for The Daily Show, for example: George W. Bush gave Stewart fresh fodder nightly like it was his job, while the next generation of comedy stars — Stephen Colbert, Steve Carell, Ed Helms, and Rob Corddry — were delivering their best version of “fake news.” But it was also a time when the show all but ignored female and gay issues — during a very Republican presidency, no less — even as Aasif Mandvi became the first regular correspondent of color to be hired in nearly a decade.

It was only in 2008 — a little past the halfway point of Stewart’s tenure — that The Daily Show began to look like what it does today: a far more representative picture of the country, and especially of the show’s young, left-leaning viewers. In the same year that saw the election of America’s first black president, The Daily Show hired Wyatt Cenac and debuted Kristen Schaal while continuing to feature sporadic appearances from Larry Wilmore and Samantha Bee. The next few seasons featured Olivia Munn, Michael Che, and Al Madrigal on the show, as well as current standouts Jessica Williams and Hasan Minhaj.

Most importantly, the “diversity” correspondents weren’t there to add meaningless color, like in a Nineties Benetton ad, but to speak on issues that mattered to their demographics. Mandvi played the “Senior Muslim Correspondent” and Wilmore the “Senior Black Correspondent” during a time when neither point of view was to be found readily on cable news, while Schaal, Bee, and Williams took turns with feminist concerns like abortion, “pinkwashing,” and campus rape. Four-fifths of the show’s “Gaywatch” segments have aired after 2008. Even the much-maligned Munn contributed a segment from a rarely heard (in mainstream media) female Asian-American p.o.v.

Stewart will host his last Daily Show on Thursday, August 6. Martin Cook

The liberal agenda, then, as set by The Daily Show, expanded dramatically beyond white/male progressive concerns. The days of mainstream politicians and comedians complaining about political correctness are fast waning. The 2008 departure of former Marine Rob Riggle, arguably the show’s last alpha-male correspondent, signaled, too, a silent admission of Stewart’s demographic privilege. No longer the nebbish underdog writhing under Riggle’s noogies, Stewart became a paternal figure to a new class of emerging comedians on his show.

None of these changes happened in a vacuum. One of the biggest challenges to The Daily Show’s progressivism came from Jezebel, which asked why the series staffed so few female correspondents. (The post went so viral — and apparently cut deep enough — that Stewart mentioned it, albeit in passing, on the show.) Comedy Central has diversified its programming, too, and seems eager, with the ghost of Dave Chappelle and the imminent ending of Key & Peele, to develop the talents of its next black male “it” comedian. And, of course, the news has fractured and diversified, not just in the direction of Fox and its friends, but also through publications catering to liberal, black, Latino/a, female, and LGBT perspectives — all of which helped viralize Daily Show segments that spoke to their priorities.

Stewart will exit the airwaves this week with plenty of shortcomings. Cenac recently revealed on Marc Maron’s WTF podcast that his effort to call out Stewart’s racial insensitivity in the writers’ room led to a shouting match. A needlessly nasty hit piece against the blue-collar New Jersey town of Bayonne by Jason Jones reflects the show’s occasional classism, while Stewart’s continuing parody (i.e., emasculation) of South Carolina Senator Lindsey Graham’s Southern accent is borderline homophobic. In 2010, a study found The Daily Show’s guests to be the least diverse of any late-night show, with 96 percent being white. Four years later, that number had plummeted to 68 percent — which, of course, is still pretty high.

Still, Stewart and The Daily Show have not only admirably changed with the times, especially when most of late-night TV still looks like it did half a century ago, but now serve as a city on the hill of the culture they’re trying to influence. The news has focused on the Republican Party’s Tea Party-induced fracturing in the last few years, but the Democrats are still cleft between their white (male) progressives and their identity-politics sectors. (Bernie Sanders, for example, is the great Vermont hope for many blue-staters, but remains a “virtual unknown” among black voters.)

We tend to praise comedians for their voice, for telling the truth when no one else will. But one of Stewart’s greatest accomplishments, especially during The Daily Show’s latter half, was to sit back and let others talk instead of speaking for them. As Cenac can attest, Stewart wasn’t consistent about this. But over the years, The Daily Show proved that political priorities change with the times and that empathy needs information and reflection to replenish itself. The news doesn’t do us any good if it’s only going to confirm what we already know. By cultivating diverse points of view far outside his experience, Stewart helped The Daily Show — and us — evolve.