Her popular brainchild is “The Daily Show,” which she and Madeleine Smithberg created in the mid-’90s for Comedy Central. The pieces came together gradually — from hiring Lewis Black early on to spoof the stock “angry talking head” to, after the first host “Kilborn-ed” his way out of the job, landing a post-MTV (and post-“Adolf Hankler”) Jon Stewart at just the right time for the comedian and show alike. The Yankees were launching their latest dynasty in this era, and now Comedy Central, buoyed early on by skipper Doug Herzog, was building its version for late night.
And so, as I sat next to Winstead some years back while on a comedy-festival panel in Washington, she was asked yet again: What spurred you to start “The Daily Show”? Her distilled reply was that she didn’t initially create the show to lampoon politicians; the true aim was to skewer the media, particularly because of the troubling changes in on-air news amid the rise of 24/7 channels. We were noticing, she said, “that TV-news divisions seemed to be spending more money on graphics than journalism.” She said that outlets were abdicating their Fourth Estate responsibilities and that comedians, if no one else, needed to hold them accountable.
And she had just the vehicle to burn past the competition come a new century’s turns in political satire. But she and Smithberg needed the right pilot.
On Thursday, that high-performance driver, Jon Stewart, will exit the “Daily Show” seat, stage (if not political) left, in his final night as host after a 16-year turn that surely exceeded the show’s early expectations. And Stewart leaves the arena of political satire radically altered.
Just consider the context: Between Stewart’s “Daily Show” debut and now, the business of satire delivery has been thrown into one massive digital blender.
“Online media mashes everything up together,” Matt Wuerker, Politico’s Pulitzer-winning cartoonist, tells me. “A late-night sketch is just as easily dropped into a Web page as a cartoon or a photo. Political cartoons, clips from comedy shows, memes, Vines, animations are all in the same space now. Some might say that they’re competing in that space, but I think it’s more symbiotic — convivial. It’s a humor storm that feeds off itself.
“Stewart and [one of] his offspring, Colbert, were in the center of that storm.”
This is part of why Stewart and his entire “Daily Show” team, including writers and video editors, have been so comedically effective for so long. They have been not only knowing of tone, but they honed how to use the graphic, the sound bite and the archived clip, juxtaposed just so, to devastating effect. And that’s a form that has fit many of Stewart’s strengths, as evidenced even before he assumed the “Daily Show” desk.
One telling early sign was in 1991, when Stewart got his time as part of HBO’s 14th go-round with its annual “Young Comedians Special.” Much of Stewart’s set featured not politics, but rather riffs on animal flatulence and “real” phone sex. Yet at one point, in perhaps the set’s most telling moment, the San Francisco audience erupted at his acting-out, or “show,” of a joke, and Stewart peeled back a bit of the curtain when he gleefully revealed: “I GOT you on the visual!” This was the technician letting us see the wheels turn for humorous effect in a way that, for a crowd, connects and endears.
Early on, Stewart also flashed a know-how for the power and potential hypocrisy of language — the sort of thing that those of us influenced by George Carlin and his incisive, playful-with-a-purpose verbal gymnastics certainly grew up appreciating. (The only time I’ve met Stewart, in fact, was to chat briefly right after Carlin was posthumously awarded the Mark Twain Prize for American Humor at the Kennedy Center; even at that event, Stewart spoofed the potency of political labels among the gullible and unskeptical.)
The power of the visual. The punch of the verbal. Throughout his run, Stewart’s “Daily Show” has deftly adopted some of the crucial tools wielded by political cartoonists for centuries — a trick that for 16 years has left numerous editorial artists with mixed emotions. On one hand, Stewart provided a popular example that political satire was not only viable, but also vital. Young viewers could have their political passions stoked — thus debunking some stereotypes about apathy — if appealed to intelligently.
On the other hand, “Jon Stewart smoked us” on deadlines, says Signe Wilkinson, the Pulitzer-winning Philly.com cartoonist. “His show was like a verbal collection of two-dozen great cartoon ideas delivered the day the news happened.”
And some of my fellow cartoonists-in-arms say that because his “Daily Show” run “raised the bar,” they were pushed to do even better — yet another effect the comedian and his writers could sometimes have on the media.
As Stewart readies his exit, I asked more than a dozen of the nation’s top editorial cartoonists about the comedian’s tenure, particularly in relation to their work as political satirists. Here’s what they told The Post’s Comic Riffs:
STEVE BREEN (San Diego Union-Tribune):
I like Jon Stewart a lot. He’s smart and funny and doesn’t seem to have a big ego. In fact, I met him once when I was on a 1998 Clinton-scandal panel he moderated — I think it was for Comedy Central — right before he took over “The Daily Show” and he was very gracious and witty. Super-nice guy. But he hasn’t affected my work in terms of how I create cartoons. I do think he and his show were good for the world of satire for a few reasons, though:
First, he showed you can be a political satirist/opinion-maker and not be a grating, unlikable blowhard.
Second, he went after both sides. [Although] he wasn’t totally balanced — he could have gone after those on the left more, in my opinion.
Third, most importantly, he helped get young people into politics and news again.
MATT DAVIES (Newsday):
Jon Stewart didn’t really affect the way I approach my own work, but he did broaden an entire generation’s appetite for political satire, so from a selfish standpoint, I benefited from the man’s genius.
As a comic/punditry delivery mechanism, TV is so different to drawing cartoons. With TV, you have the rapt attention of your audience for longish stretches; with a cartoon, you have to get in and get out quickly. I always figure I have a second or two at most to throw the custard pie. Although I remember reading that Jon considered himself to be exactly like a political cartoonist. And I also remember wondering how well he could draw.
DAVID HORSEY (Los Angeles Times):
I’ve been a fairly devoted follower of Jon Stewart and “ The Daily Show” over the years, and most nights, while watching and laughing, I have thought to myself in distress, “Why didn’t I think of that?!” It helped to be reminded that Stewart had a team of writers at his command, while I was flying solo to come up with my cartoons. Still, though, it seemed as if I could have pushed a little [further] to match the smart satiric insights into politics and the media that Stewart delivered on just about every show. The intelligent comedy of Stewart, as well as Stephen Colbert, made typical political cartoons seem even more anachronistic than they already have become. Little line drawings with too many elephants and donkeys and Uncle Sams just could not compete with the multimedia power and hipster sarcasm of Stewart’s show.
On the other hand, having the bar raised by Stewart has been good for cartoonists. For those of us who are interested in pushing past the old conventions of the art, Stewart provided a powerful, positive challenge.
Stewart also reminded America that political satire is serious business. It is not just telling a joke about the president — it is taking a hard look at politicians, the media and the voters and rendering tough judgments about the dangerous shortcomings of them all. In particular, Stewart performed a great service to the nation by highlighting the vapid and self-absorbed nature of political discussion among the ranks of talking heads in the 24/7 world of cable news. This did not cause cartoonists and commentators in the print media to simply feel smug — it compelled us to depart from the chattering crowd and search for fresh insights.
Frankly, I worry that the nation’s political dialogue will become more staid and stupid without Jon Stewart calling out the idiots night after night.
KEVIN “KAL” KALLAUGHER (Baltimore Sun and The Economist):
I think Jon Stewart has profoundly altered the role of satire in American discourse for the better, while helping lift dispirited cartoonists along the way.
You could easily imagine that “The Daily Show” was a threat to the long-suffering editorial cartoonist. In each episode, the writers of “The Daily Show” produced the equivalent of 25 editorial cartoons with glee. Large audiences on air and online loved it. The gags would be live for days more online and in social media.
This would leave the dwindling band of satirical scribblers like myself a little uneasy. We were now left with a riddled carcass of current events to pluck apart. So many of the best gags, creative angles and targets of scorn were cornered by “The Daily Show’s” comedic geniuses.
Despite this, I think “The Daily Show” helped the editorial-cartoon community. This new big kid on the block raised the bar for our clan. In return, we needed to raise our game to survive, and raise it we did. I think there is a lot of novel and creative energy in the field today that is, in part, fostered by the new competition from television satire like “The Daily Show.”
I also believe Jon Stewart proved something to America that we cartoonists have long known: Political satire is popular. Readers love our satirical cartoons… it’s just [that] the newspaper publishers need to learn this universal truth.
KEITH KNIGHT (“The K Chronicles”):
I think Stewart has really affected the landscape — just thinking about all the great performers: Carell, Colbert, Oliver, Wilmore [etc.] that broke through via the show. But, most importantly, Stewart’s show exposed Fox News as the modern equivalent of pro wrestling — more so than anybody else.
In truth, I avoided watching it, because I didn’t want it to influence my own work. But I’m always catching up via clips on YouTube.
MIKE LUCKOVICH (Atlanta Journal Constitution):
Having Jon Stewart around was good for me as a cartoonist. His satire, and wit, is so good that it’s pushed me to do better.
His genius is making strong points without sacrificing humor. Anyone doing political commentary knows that that is what you aspire to, but that it’s really hard to be consistently great the way Jon Stewart’s been.
Through social media, it’s easy to find clips of “The Daily Show,” so even if you don’t watch much TV, he’s available. That’s one of the reasons I believe Jon Stewart’s had a big impact on young people. His show has been a powerful rebuttal to the crap spewed by Fox News. I think it’s helped younger people shape their political views by showing the way Fox cynically misleads its audience. I don’t think he’s had much of an impact on Fox’s old, white viewers who probably don’t watch him.
I’m going to miss him.
JIMMY MARGULIES (King Features and amNEW YORK):
I can’t say that Jon Stewart’s reign on “The Daily Show” has had a direct affect on my work as an editorial cartoonist, but I definitely appreciated his showing that there is an audience for political satire. I wish that editorial cartoonists had the influence that Jon Stewart had in ridiculing political, social and cultural events.
It often seemed that whenever some event or personality tailor-made for satire came along, it was common to hear that this would be great fodder for late-night comedians, which encompassed not only Jon Stewart and Stephen Colbert but Jay Leno, David Letterman, etc. I wish that my profession were included in that thought, as well. But even with the reach of the Internet, editorial cartoonists have been overshadowed as the premier political satirists nowadays.
How I wish that Jon Stewart’s showing that political satire was really popular could have translated into a more secure job environment for those in my field. But the declining fortunes of the newspaper business had an even greater impact, and during the same period that Jon Stewart was on “The Daily Show,” staff positions for editorial cartoonists at daily newspapers were reduced to about 50-percent of what they had been.
Maybe the success of “The Daily Show” had the effect of showing that newspapers were not able to adapt to the changing tastes and values that Jon Stewart was successful in capturing.
JACK OHMAN (The Sacramento Bee):
I think Jon brought a political cartoonist’s sensibility to the news, and I felt that he was pretty ecumenical in his treatment of both political parties.
He was highly influential in many ways. Stewart managed to become a primary news source for a generation of people who either didn’t trust traditional news sources or have time to invest in them.
My generation was raised on CBS News, and the Stewart generation saw the news as B.S.; Stewart cut through the traditional filters to get to the essential truth of the news, which is what a lot of good political cartoonists do. And, I think, Stewart was highly informed himself, liked the news business, and cared about it. So he was the leader of an institution that performed a valuable function in society.
I really think he was instrumental in how political candidates now frame themselves: “How will this play out on ‘The Daily Show?’ ”
Interestingly, to my knowledge, he never had a political cartoonist on the show, and I always wondered why. There are a lot of them who could have made a great contribution to that show.
MIKE PETERS (Dayton Daily News):
I remember in the ’70s, when a story came out that the fabulous singer Claudine Longet was convicted of negligent homicide in the shooting of the famous skier “Spider” Sabich. I didn’t see any cartoons that were done on the subject — I couldn’t think of any myself — and I thought maybe it was too soon anyway…until that weekend, when “Saturday Night Live” took the beginning of ABC’s “Wide World of Sports” that showed [the skiing wipeout]. “SNL” took that tape and called it the Claudine Longet Downhill Race. And before each skier fell, there was a gunshot, and the announcer would say, “Boy, she really hit the mark on that one. ” It was hilarious, it wasn’t fair, it wasn’t kind — but [it was] truly funny. I learned from “SNL” when something bad happens, you can still do satire on that subject the next morning.
That’s what Jon Stewart has been teaching us for the last 16 years. He’s brilliant, funny and spot-on. Nothing is untouchable and after all these years, I’m still learning from a master.
Thank you, Jon, You will be dearly missed.
JOEL PETT (Lexington Herald Leader):
I don’t think “The Daily Show” has affected the way I work, except maybe to push me to try and keep my tongue in the same “league of cheek” as his writers. And yes, I think pretty much all mockery of power is positive for the republic.
It’s no secret that comedians have long been constructing mega-mansions on chunks of satirical real estate that were once squatted on by editorial cartoonists. Our best efforts aside, George H.W. Bush’s simpy, “not-gunhh-dewit” caricature was all Dana Carvey, and that was nearly three decades ago. It was particularly telling for me that in the  documentary about the great Washington Post cartoonist Herblock, both Jon Stewart and Lewis Black got a lot of airtime, as the clear heirs apparent, at least in the view of the filmmakers, to Herb’s legacy.
As an ardent fan of a slew of political comics, it’s with a begrudging respect that I cede the main course of this feast.
But I and the 50 or so newspaper editorial cartoonists still working continue to relish the crumbs.
JEN SORENSEN (The Austin Chronicle et al.):
It probably goes without saying that I’ve been a longtime fan of “The Daily Show” [and “Colbert Report"]. Those shows shared a similar sensibility to that of many alternative political cartoons, and the writing could be super-smart and inspiring. I often found myself watching them online just to make sure I wasn’t duplicating something they’d already done. That was always my second thought after coming up with a good idea: “Better make sure Jon Stewart didn’t do that this week!”
In some ways, “The Daily Show” felt complementary to my own work, in that it whet people’s appetite for political humor. At other moments, it felt a bit like competition, particularly when websites would devote regular real estate to embedded video clips that might have gone to a political cartoonist in a previous [non-digital] era. I don’t think I lost any gigs over that, but it was hard not to think about sometimes.
As far as America’s larger political dialogue is concerned, “The Daily Show With Jon Stewart” has been invaluable. It was an education in U.S. politics, with jokes. I do feel like his departure is the end of an era.
SCOTT STANTIS (Chicago Tribune):
Editorial cartooning has won and I couldn’t be sadder. For decades, editorial cartoons graced the pages of newspapers, afflicting the comfortable and comforting the afflicted. People loved them. [Then] the Internet and memes came along, using much of the same devices as editorial cartoons; subversive snark with a shiny satirical veneer. Then came “The Daily Show With Jon Stewart,” who took the devices, the snark and the satire to a whole new level, making what amounted to video versions of editorial cartoons. Biting wit that punctured the smug flesh of the overblown with laser-like precision that hit its target so perfectly it was impossible to see their hapless victims in any other way then the way “The Daily Show” presented them. Brilliant stuff. A lot like when the great editorial cartoonist for The Washington Post, Herblock, drew then-Vice President Richard Nixon coming out of a sewer. Nixon was never able to shake off that image. Mostly because it was so true. If not to the facts, at least to the true nature of its target.
That is what Jon Stewart did so brilliantly on “The Daily Show.” [He] embodied the spirit of that great American political satirical tradition. And now we’re losing him. Which is a shame for the country, but maybe now I can have my profession back.
SIGNE WILKINSON (Philly.com):
Jon Stewart smoked us. His show was like a verbal collection of two-dozen great cartoon ideas delivered the day the news happened.
The only edge we still have is that my mother can’t cut out a Jon Stewart show and show it to her friends at the her retirement community.
MATT WUERKER (Politico):
“The Daily Show crew created a new genre of made-for-TV political satire. While Jon Stewart is a comic genius, the tragedy is that if he only had some drawing skills, he could have been a great political cartoonist.
Like pretty much everyone, I’m a huge fan. Stewart revolutionized late-night TV comedy. He brought politics into that time slot in a way no one had succeeded ever before, and created a genre that’s given us Colbert and Larry Wilmore. Though, I have to say, it would be nice if there were [more] women allowed into the boys’ locker room, too, someday.
You ask how “The Daily Show” changed things for “print” satirists; I think you need to change that to “print and pixel.” And I don’t think he authored this change, but the reach of his show highlighted the change.
That big change was the convergence of video, print and cartooning online. Online media mashes everything up together. A late-night sketch is just as easily dropped into a Web page as a cartoon or a photo. Political cartoons, clips from comedy shows, memes, Vines, animations are all in the same space now. Some might say that they’re competing in that space, but I think it’s more symbiotic — convivial. It’s a humor storm that feeds off itself. Stewart and [one of] his offspring, Colbert, were in the center of that storm. They raised the bar and brought a new sharpness and pace to political humor. The political inanities of the day would get lambasted every night at 11. Granted, he did have the advantage of a big staff of writers, but there’s no doubt his fleet-footed and acid humor did raise the bar for the rest of us.
ADAM ZYGLIS (Buffalo News):
In many ways, Jon Stewart has been the standard-bearer of searing satire and truth-telling in the media for much of the past decade-plus. He’s illuminated the absurdities and hypocrisies of American politics in a way nobody could match. Much of this is due to the fact that he actually reported information in a selective way to get at the truth, meaning that the viewer could walk into his show ignorant and leave educated. That’s the unique beauty in his craft.
The visual satire of an editorial cartoon is quite different in its delivery and the way in which it communicates. It’s a contemplative art, as [Patrick] Oliphant described. It has more of a lingering visceral appeal. It’s an art in which we depend on our readers to already be informed. Many of us are more philosopher than entertainer, when compared to our Stewart-esque counterparts. And yet Stewart was a master at being equal parts entertainer, philosopher and educator.
Over the years, “The Daily Show” had an impact on me in the way it aggressively mined the fields of irony and hypocrisy. It has done so like no other, and it’s been inspiring to see. I especially admired the way it hit hard on the media. 24/7 broadcast media can be a very depressing thing to consume these days, considering its self-proclaimed role of holding people accountable. And Stewart, in turn, held the media accountable.