CBS SF Talks to Comedian and Co-Creator of 'The Daily Show' Lizz Winstead (Part 2)

By Dave Pehling

SAN FRANCISCO (CBS SF) -- A veteran stand-up comedy talent who started her career in the early '80s, Lizz Winstead is perhaps even better known as one of the creative forces behind both "The Daily Show" and Air America Radio and as an astute political commentator and abortion-rights activist.

CBS SF published Part 1 of this interview last week. In Part 2, Winstead talks about her time working at Air America Radio, "The Daily Show" and one comic's current obsession with cancel culture ahead of her performance presented by Talent Moat at the Verdi Club in San Francisco on Saturday, Nov. 6, at 8 p.m. with support from Bay Area product Nato Green.

CBS SF: Did you have any radio experience before you started Air America after you left "The Daily Show?"

Lizz Winstead: No! The one thing I learned as a young woman: I watched men who had no business being in charge just say "yes" and do s--t with confidence. And I decided to do that. When it was stand up, I did that. I had no experience. I had done one TV production thing before "The Daily Show," and I also was the head writer and was asked to create it.

Air America? I had no idea about radio, but I'm jumping in and doing this. It seems I just try to be as open as possible and surround myself with people who know what they're doing, and hear what they're doing and what they have to say. And then add my own spin on how we could maybe do it different and create a mash-up, hopefully, of something new.

And that's what we did. Air America radio was a grand experiment that should have worked, but we had a financial grifter who lied about how much money we had -- and there's a whole documentary about it, you can watch it. But we had a radio format that was working, and then it collapsed. And you know it worked, because a lot of stars came out of there. Sam Sedar and Janine [Garafolo] and, of course, Rachel [Maddow]. And it was, it was really a wonderful thing.

I have to tell you, the day I got fired was when they had turned over the reins from the grifter to a guy named Danny Goldberg, who managed Nirvana and really didn't have any radio experience either. And one of his first decisions as somebody with no experience was that comedy wasn't a good tool for social change.

So he fired me, he fired Marc Maron, he fired the comedy writers. He moved Rachel Maddow to 5 a.m., moved Chuck D to the weekends and replaced our show with Jerry Springer. And I have to tell you that in the scope of things that I never thought would happen to me in my career, I never thought I would be replaced by Jerry Springer. I thought I could guarantee that [laughs]!

CBS SF: It does seem to be catering to a lower common denominator that had little or nothing to do with the radio network. That is a very weird move. So the show with Chuck D, you were a co-host with him and Rachel Maddow?

Lizz Winstead: For two years, Chuck D. Rachel Maddow and I had a show on Air America together. Chuck and I go way back. And that was like a joy to have this three headed Hydra of wildly divergent life experiences come together, I was so fortunate to get to know him as a human.

And also to get to know like, hip hop icons of mine. I don't know a lot about hip hop. But I love political hip hop. And so it'd be able to interview Melle Mel and Rakim and all of these people who had come up through hip hop who were saying something was pretty great.

CBS SF: I did want to touch a little bit on "The Daily Show," if we could. Do you feel it's ironic that this show you started with the aim of satirizing the news became actually one of the main ways a wide scope of people would actually receive their news?

Lizz Winstead: You know, it's funny. Because part of my stand up was based on media criticism from the get go during the first Gulf War, and I did some one woman shows about it, so I've always been somebody who has been observing what s---ty news looks like. And so I knew there was a marketplace for it, because my audiences were responding to it, right?

What I never could imagine was that the media could become so derelict in its duty that "The Daily Show" could live for 25 years. Because it's just watching and mirroring the trends of media and it lives on because media keeps stepping in it. It's kind of astounding to me how how many softballs are thrown, how few follow-up questions are asked, how they ignore these larger things. Both-sides-ism is very real and very terrifying.

And growing up, if you look at the trajectory of cable news where it was, you know, the "trial of the century" of the week in the '90s and all the car chases and all the lack of news that it built itself on, we would call it the fake news. We called ourselves the fake news and then we called that the fake news. And now what the people who call the fake news "the fake news" are believing is fake news and not the truth.

And it's a roller coaster of chaos. I think for people who do comedy and respond to it, our jobs have never been more important, just to weed through it. If not for just the fact that every day -- if you do a show, or you're on Twitter, or social media or someplace -- and you can lay out why this doesn't make sense, people can feel 100% gas lit.

I mean, it is shocking that I don't see people walking around with huge purple bruises on their foreheads from just slamming their heads into the wall constantly. But I think that's a role that I enjoy playing. And I think that it's what I want to do. And the more I hear whining and complaining about cancel culture, I feel like, you know, you can't really be canceled if you're screaming about being canceled while hosting "SNL" or from your eighth Netflix special.

And for years, there was silence when anybody else had an opinion and their records were burned. I was a feminist. You think I got booked a lot? No, I didn't. Do I complain about it? No, because I knew that I had to grow the marketplace of ideas and find my audience. I'm so curious as to when the marketplace --when your stuff is on the shelves, and people don't like it and they don't pick it, but other people pick it and made you famous; are you just mad that you don't have the right people buying your product? Because you seem rich. You seem successful. You seem to have an audience. You seem to have fans.

I know you have fans, because they come after me with regularity when I'm like, "Calm down!" People get to have a say. That's what happens! That's what happens. I don't understand the victimization of people who think they deserve, with every word they say, adoration.

The second it passes your mouth, everybody gets to interpret it and have feelings about it. That's what makes it exciting. And that's what makes it a platform that is, you know, where are you going to land? If you truly want to stand behind what you say, then stand behind it. And that's great. But if you feel like you stepped in it, you want to change, then apologize and move on. I think that's just the way it goes. But take the hits.

CBS SF: I have not watched the latest Dave Chappelle special that's stirred up so much controversy. My son actually was the one who told me about it. He was looking at his phone one morning a couple weeks ago and said, "Uh oh. Dave Chappelle did a whole special on trans people." And my response was, "Well, that sounds like a lot of trouble. Why is he doing that?" Especially for someone who I felt had said some of the most powerful things about recent events, as far as comedians go...

Lizz Winstead: Dave Chappelle was -- hands down -- my favorite comedian of all time. 100%. I guess what I learned about Dave is that I don't see that he has an intersectional lens. I don't see it. And not understanding, profoundly, the struggles and the pain that people go through, in the name of "It's just a joke." People get murdered, you know? Trans women, especially black trans women, if some cis dude finds himself of attracted to a trans woman, they will oftentimes go to great lengths to harm that person. Because they're angry that they have feelings towards that person.

And to not profoundly understand that every day that a trans person walks the earth, they understand there's a world for people that want to harm them. And unless you are intimately in relationships with folks who are living that and walking that, you gotta shut up. It's not helping. It's really hurting and harming people. And it makes me feel profoundly sad.

I don't know what information he's going on, and that's Dave's decision. I just know that in the world I have grown to be part of -- and that's been a larger part of my world; a more intersectional life for myself -- I have seen and what I want to hear from people out there in the world responding to it, is something different than I think he might be offering up right now.

CBS SF: The last question I had about "The Daily Show" was something I noticed as I was doing research for the interview. My wife had forwarded me the LA Times article that came out earlier this year about the streaming special on the 25th anniversary of the show you and Madeline Smithberg put together with a couple of the early "TDS" correspondents. I didn't realize how difficult it was to come across those early clips until I was looking myself. On YouTube you can find Craig Coburn's last episode and a handful of individual segments, and that is it.

Lizz Winstead: And I still don't know why. And I would love for some reporter to get to the bottom of why the origin story and those clips don't exist. Because it does a disservice to the evolution of the show. Also, those early shows are a reflection of what the media was like then; the "if it bleeds, it leads" local news. Only one cable channel was out at the time, and then all of a sudden Fox and MSNBC burst on the scene in the same year, four months apart.

There was a lot of really interesting things that go along with the body of work that is "The Daily Show." I've just gone on with my life and done my stuff for a lot of years, and now I'm running an organization that takes the tone of "The Daily Show." We're launching our own talk show December 2, called "Feminist Buzzkills Live!" on YouTube.

It's gonna be a weekly show that's going to be edgy and funny and talking about all of this stuff around reproductive health rights and justice that you don't hear about the news. We're gonna have comedians on and experts from the field and it's gonna be great. But when you look at it, it's very sad to me that people are like, "I had no idea two women created 'The Daily Show.'" And that's by design. That's by design of people who have been in the process and remained at that show, who they talked about, what they talked about and what they didn't talk about. It's just indicative more of sexism and what happens.

CBS SF: Which leads to the one other question I had; it almost seems that after your departure, when Jon Stewart became the host, the show actually really came into what it seemed like your vision was...

Lizz Winstead: Yeah, it took a man. It took a man to say the exact same things that we were saying. And not only were we saying it, the network found it annoying. They really wanted it to be a pop culture show with a little bit of news. And I pushed back on it really hard, because I was like, "No one's gonna remember a pop Culture Show." And if you want to have celebrity guests on, why would you s--t on them? Why don't we take on the big fish? Why don't we expose the big fish?

So yeah, it took Jon Stewart coming in and saying the same things, and then all of a sudden it grew into this political juggernaut. It's interesting, because I've been seeing interviews on his new show, where it's like, "I really want to do comedy and tackle a single issue, and then give a call to action." Oh yeah, right. Exactly like what we're doing over at Abortion Access Front!

So I think that you realize how much how much sort of institutional misogyny still exists and has existed. And you can get bitter about it, or you can realize what's available to you, grab it and learn it. I know how to make graphics. I know how to cut video; I'm not very good, but I know how to cut video. I know how to do shows. I take to all the spaces available for me to have access, and I stand on them. And I I plant my flag, because why not? I'm not going to hold myself back, because the world is determined to do so.

CBS SF: I guess what I was also getting at was, with the shift in direction that the show took and given that Madeline Smithberg was still there, was there any temptation to go back as that shift was happening?

Lizz Winstead: Yeah, Jon asked me to go back a couple of different times, and I felt like, "You got this." And me coming back there and them just having one more voice on a show, rather than, "Let's get some more stuff like this out there in the world!" That was a better plan. You don't just want one place: "Let's just keep adding on to this one grocery store in this neighborhood."

That's a terrible idea! Let's build better. Let's have fresh food and a bunch of different places, so that different people can access it and it's a growing trend. So that was my whole thing. Watching the trajectory of the show, watching it become a fully realized, really smart thing was awesome. And it allowed me to move on and then replicate it in different ways. but having that kind of information and tone out there.

Because the worst thing that could happen was if I left and they didn't hire Jon, and they hired somebody else, and it became a pop culture show that died. Then we would have never had examples for with which we could launch John Oliver and Sam Bee and Stephen Colbert and Brian Unger and Amber Ruffin and Larry Wilmore, and all these shows that have taken their cues from that. It got to be a provable entity. Air America Radio wouldn't have happened, you know? So I feel really, really glad about that.

Lizz Winstead performs in San Francisco on Nov. 6 at the Verdi Club. Tickets and information here.