That Time I Got to Interview S.E. Cupp

Just a few months after meeting her for the first time, I got to interview S.E. Cupp at an AFF Happy Hour. This photo is from when I met her because reasons.

Here’s my write up, for and originally published at Doublethink magazine.

An Interview With S.E. Cupp

Interviewing a polished, professional television personality like S.E. Cupp is a pleasure. The verbal tics are absent. Cupp speaks like your favorite writer writes. Which makes sense, because a writer is what Cupp started out as, and writing is still her first love. But it only makes sense, considering her stunning looks, pleasant voice and verbal precision, that she’d be roped into a television detour.

I got to sit down with Cupp when she stopped by a Doublethink happy hour Wednesday night. She arrived, stunning in impeccable hair and makeup, literally right after wrapping up an episode of CNN’s new Crossfire, which she hosts along with Stephanie Cutter, Van Jones, and Newt Gingrich.

We grabbed a booth at Mackey’s Public House in downtown D.C. and got right into it as fans clamored for the chance to meet her.

How has your time at Crossfire been?

It’s really liberating to be able to talk about one topic in a night.

Is this something you’ve always dreamed of?

No! I don’t know how I’m here. I’ve always wanted to be a writer. And writing jobs are what I had through college and after college. When I wrote a book about politics, my publisher put me on TV to promote it. I was writing and going to TV to support it. And then it became a full-time job. And, it’s been a lot of fun. I’m still, very much a writer. I’ve got a weekly column at the New York Daily News and a monthly column at TownHall. I still write books. That’s still very important to me. But, doing TV is a different muscle.

You have to have fun, so the viewers have fun. And I like answering the questions I know the people at home have.

How do you break down an issue to be simple enough for television without being patronizing?

I’m not smart enough to be patronizing on television. I’m really not. And that’s not false modesty, I’m smart. But I think to be patronizing, you really have to think you know more than everyone else. I know I don’t. So, to me, the challenge is to be unpredictable. So, I know what I think. I have to constantly remind myself that not everyone knows what I think. And I have to ask interesting and provocative questions. And bring up points that I don’t think anyone’s brought up. Because I think in this business you do the best service when you present a panoply of ideas. One person’s ideas they just spout at you all day, I don’t think you really learn a lot about the world. You might learn a lot about that person’s ideas. But I try to incorporate a lot of different ideas, a lot of opinions, in addition to mine, so we can actually explore an issue in a meaningful way.

Do you worry about following other prominent television news anchors and saying something that will get you in trouble?

I think in this business you have to worry a little about crossing the line. I never want to offend people. That’s not an interesting exercise for me. I’m sure it is for other people. It’s not for me. And I never want to cross a line that damages my credibility.

That said, you can’t really go on with a governor. You can’t go on restricted. You have to go on like, “I’m having a conversation with my friends. And I’m gonna say what’s on my mind.” And hopefully you have an internal governor that sort of guides that for you. Because if you go on TV scared every minute of what you’re gonna say or offending someone, it isn’t interesting. And it doesn’t feel real or authentic.

So it’s a balance. It’s a balance of being deliberate, with what you say, knowing, okay, I’ve got a controversial topic tonight, I’m gonna be careful. Or saying, okay, this is really lighthearted, I’m not going to plan for this. I’m just gonna go out and say what’s on my mind.

It’s knowing where the line is, and knowing when you mean to cross it, and when you don’t.

Do you think it’s harder for conservatives?

You know, I’ve seen conservatives get in trouble [and] I’ve seen liberals get in trouble. I think it takes a longer time for audience outrage against liberals to really reach maximum effect than it does for conservatives.

But conservatives do pretty well. I know that there is a media bias. But at the same time I’m reluctant to dwell too much on it. Because if you look at the success of Fox News, of conservative talk radio, of conservative print media, we really own a big market share of broadcast and print media.

We do really well. So it’s hard to feel bad for ourselves too much. Even though there is a double standard. There is a media bias that exists. But we’ve luckily found a way around it. Instead of playing on their channels, we’ve created our own.

Do you think it’s harder for women?

I can’t speak to the male plight. But when I’m speaking to my male colleagues about some of the things that are directed my way they share with me that it’s not quite the same for them. Being a woman, you get both the hatred that O’Reilly gets and Sean Hannity gets, we also get, along those same lines, misogynistic hatred that they don’t get.

But also, and this is something that very few of us talk about, we get the stalker-y, “I’m in love with you” kind of thing, which – I’m sure some men get it, but that’s predominantly a phenomenon that women pundits and women on television have to go through. And nothing feels more violating, honestly, than the death threats and the uncomfortably intimate emails.

That’s something that you just compartmentalize, and you say, I’m going to do this job regardless. And whatever happens, happens. Otherwise, it would paralyze you. You wouldn’t do this, because it’s not fun to be the object of that kind of attention. But, you just put it aside and realize that other people are going through it too and hope for the best.

How do you balance offering libertarian views in the conservative sphere?

I think it’s a healthy tension. I think, rather than try to get all of us to agree on everything, it’s much more interesting when we don’t. I wish we would do it civilly. And not calling each other out or trying to kick people out of the movement. I really do believe there should be a big tent where we celebrate our intellectual diversity.

I’m glad libertarians are here. I’m glad conservatives are here. And I think at heart, most of us are internal libertarians. We have an immediate aversion to government control, Big Brother, nanny state stuff. We really are self-reliant and independent.

The conservative would suggest that a lot of the libertarian impulses and policies are just hard to implement. They’re not as practical. I think if we can work together as conservatives and libertarians we can turn those libertarian impulses into conservative policy that’s actually winnable, electable, sellable. And that’s when we all win. But when we stand on opposite sides of the aisle dividing conservatives and fight with each other, I think that makes for some interesting arguments, but doesn’t necessarily move us forward.

But are there drawbacks to associating libertarian ideas with a tainted social agenda?

Probably. I wouldn’t say tainted. As a social conservative, I think there’s a way to stand up for those ideas that’s, in fact, not entirely unlibertarian. But, I think if libertarians wanted to exist on their own island, sort of an isolationist libertarianism, unaffected by the part of conservatism they disagree with, hey, they’re free to do that. I don’t think that would be a long-term winning strategy for libertarians. Ron Paul didn’t become President. Ron Paul’s never going to become President. Rand Paul has a slightly better chance. But I don’t think that he’s going to be the next President.

So I think, again, this isn’t an either/or. I think we should be working together. I wrote a column a long time ago about Rand Paul needing Paul Ryan and Paul Ryan needing Rand Paul. Ryan could stand to be a little more libertarian. And I think Rand could stand to be a little bit more conservative. And if they worked together, I think our party could be unstoppable.

If it’s not in the interest of libertarians to win elections, then we’re just talking nonsense. No one cares about any of the conversations. I want conservative values to be implemented. And I don’t care if a libertarian gets us there or a Republican gets us there. I want us to get there. And I want us all to work together.

What are some of those conservative values you want implemented?

Number one is tax reform. You wouldn’t find a person in the country whose daily life is impacted by anything other than taxes more on a day-to-day basis. It’s everyone’s first concern. How much they’re making, who’s taking it, what it’s going to, what do I get to keep? And the tax system is so burdensome. No one understands it. It’s punitive on all the wrong people.

So I think if Republicans could come up with a winning message on tax reform, that’d be huge.

I’m gay rights and pro-life. It’s not really part of my agenda to make policies on either of those issues. My policies are mostly fiscal and then some national security stuff. But I think [the issue of] taxes is number one. It crosses all parties, all genders, all ethnic groups. I mean, it affects everyone.

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