Lizz Winstead’s road to late-night legend started in stand-up clubs in Minneapolis, then a New York walk-up where her neighbor, Madeleine Smithberg, hired her to be a segment producer on The Jon Stewart Show. When that ended, Comedy Central’s new president Doug Herzog asked them to build a fake newscast called The Daily Show.
Winstead wanted it to feel like real news. Her early misfire was insisting on no studio audience. After a quick course correction, the show’s DNA took shape: straight-faced correspondents delivering nonsense like it was gospel. Brian Unger, a real news pro, taught the team how to light and frame segments like network TV—and how to sell the joke through tone, not punchlines.
Winstead fought to make the show more political, less celebrity-driven. “Pop culture was candy,” she says, “but the press is what shapes reality.” When network execs questioned the direction, the writers threatened to walk if she was pushed out. She stayed, setting the stage for The Daily Show’s identity as a sharp, media-savvy satire.
Craig Kilborn, the show’s original host, had perfect delivery and local-anchor swagger. When Jon Stewart took over, the tone shifted—Stewart became the voice of reason, correspondents the clowns. Winstead loved that evolution. “He found the heart of what the show could be,” she says.
Since then, Winstead has applied that same ethos to everything she touches—from co-founding Air America Radio to producing and performing comedy that fuels activism.
As she tells Mark Malkoff: “There’s no reason to talk to someone who’s full of shit and not hold them accountable. Otherwise, I’m just normalizing the garbage they spread every day.”
This week on LateNighter’s Inside Late Night podcast, Winstead talks about the scrappy beginnings of The Daily Show, the battles that defined its voice, and why satire still matters when the stakes are real.
Click the embed at the top of this post to watch now, or find Inside Late Night with Mark Malkoff on Apple Podcasts, Spotify, YouTube, or wherever you listen to podcasts.
