IT WAS 1996, AND COMEDY CENTRAL PRESIDENT DOUG
HERZOG WAS IN A QUANDARY. Politically Incorrect was about to
ESPN’s Craig Kilborn signed on to fill that role, and the cocky-but-likeable host
jump ship for ABC, leaving the fledgling comedy network without a late-night
the likes of Brian Unger, Stacey Grenrock-Woods, and Frank DeCaro—all of
talk show—a vacuum Herzog very much wanted to fill.
whom had news backgrounds—to serve as early talents on the show.
He had a vision: a daily show that could be both funny and topical, and that
They were “this accidental family,” as original correspondent Beth Littleford says.
would stand as the network’s flagship program. But his decision to hire Madeleine
And they were one of a kind.
sat behind the anchor desk for the program’s first 386 episodes. They also tapped
Smithberg and Lizz Winstead as co-creators would have consequences for latenight TV, comedy, and politics far beyond what he could have seen at the time.
“The Daily Show’s responsibility was to be smart and funny, and our [ethos] was to
expose hypocrisy in the media and politics,” Winstead says. “There was so much
Smithberg, a former talent coordinator and segment producer for Late Night with
filler on the news channels, and we wanted to talk about important issues that
David Letterman, had previously collaborated with comedian Winstead on the
we could satirize.”
ill-fated Jon Stewart Show. (In an odd turn of events, Stewart began his stint as the
host of The Daily Show the year after Winstead departed in 1998.)
Most of the ensuing twenty years of The Daily Show—especially Stewart’s
tenure—have been exhaustively documented. But sorely underrepresented (if
The pair had been swatting around a different idea for a Larry Sanders–style satire
not quite lost) in those retrospectives is the headiness of the early years, before
that would depict a failing network and incorporate clips from its terrible shows.
young people would claim it as their most trustworthy news source and before
Herzog said he couldn’t afford that venture but wanted Smithberg to helm the
sitting presidents would grace it with interviews.
still-untitled daily show.
It was a time when Herzog and Unger would battle over the number of sex toy
Smithberg had recently declined Comedy Central’s proposal that she head the
references that could be made in one episode, when DeCaro’s modus operandi
network’s programming but salivated at Herzog’s pitch: she would have an entire
was cramming his “Out at the Movies” segments with double-entendres—and
year to experiment with the show, and wouldn’t even be obligated to do a pilot.
when comedic minds finally learned how to successfully mock the news.
“That type of opportunity doesn’t exist anymore,” she says.
“If you ask Doug Herzog, he will say the first year of The Daily Show was the most
fun he’s ever had,” Smithberg says. “Because we were stumbling into brilliance.”
“We wanted The Daily Show to do something that hadn’t been done before,
satirizing the media landscape [and] not just covering the news like [SNL’s]
To give that time its proper due, and to celebrate the twentieth anniversary of The
‘Weekend Update,’” Winstead adds.
Daily Show’s creation, FLOOD convened Smithberg, Winstead, Unger, DeCaro,
Grenrock-Woods, Littleford, Vance DeGeneres, and writer J. R. Havlan to provide
Smithberg and Winstead were the captains of the ship, but they needed a steward;
an oral history of the show’s early years.
FLOOD
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