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W. Kamau Bell is everywhere these days. The self-described "sociopolitical comedian" stars in a CNN documentary travelogue show called United Shades of America, touring the country—San Quentin to Ku Klux Klan meetings to our own fair city—and asking tough questions about race. He also hosts three podcasts, including Politically Re-Active, in which he and fellow comedian Hari Kondabolu attempt, via sharp interviews and silly humor, to make sense of the side show that is our current political situation.

Onstage, Bell is an affable performer who delights in stoking discomfort in his audience—which, we expect, is precisely what he'll do when he hits Portland on Friday, October 21. In advance of his Aladdin Theater shows (at the time of writing, there are still tickets available for 10:30 p.m.!), we caught up with him about parenthood, the questions he'd ask a post-presidential Obama, and why he's decided to luxuriate in sadness.

We’re talking on Monday, October 10, right after the release of the 2005 Donald Trump tape and Sunday’s debate. What’s your take on what’s just gone down?

I was with my wife and a couple friends of ours who also have kids. The debate ended, and we all just went “aauuuuhhhhh.” There was no sense of victory or anger. I think we all felt ashamed for democracy. Shout-out to Anderson Cooper and Martha Raddatz, who did the best they could to create the circumstances for debate, but the American presidential electoral process doesn’t create space for that. It’s funny to me that we’re calling this debate, because it’s not anywhere in the vicinity of what an actual debate is. That was essentially sports talk radio about politics. Wanna see people, some of whom you might respect, snarl at each other? Tuesday night on CNN! 

The other thing is that there’s no better proof of the reality of male privilege, white privilege, white supremacy than Donald Trump being able to tromp all over the stage. At no point does anybody come up and wrestle him to the ground and say, “Relax.” The way you would do a kid—just hold them and say, “Stop talking.” The way I do with my daughter sometimes—I just pick her up and hold her to my chest and go, “Relax.” Someone needed to go up to him and hold him and say, “Stop it. Just stop. You’re not listening. You’re not paying attention. Stop it. Breathe. Breathe.” That’s not something anyone could get away with unless they’re a rich white man.

How much awareness do your daughters have of Trump?

My youngest daughter is almost two, so she’s not aware of it. My five-year-old said several months ago—and I’m not sure how this came up—but she said, “I don’t like Donald Trump’s rules.” And I was like, that’s a great way of putting it. Yes, he has bad rules.

Did you ask her what she meant?

She understands that under Donald Trump’s rules, she and people like her wouldn’t be able to live the lives they want to live. On a very basic level, she understands that she and friends of hers wouldn’t be able to live and be happy if Donald Trump was in charge.

You co-host the podcast Politically Re-Active with fellow comedian Hari Kondabolu, and you’ve had quite the slate of guests: Lindy West, Rachel Maddow, Van Jones, Shaun King. Got any dream guests?

I would love a post-Obama presidency interview. I want one now, but I would love one after it’s over. I know he went to Marc Maron—can I get him after he’s done? I think that would be amazing, just to see once the air goes out a little bit. I’m really excited—I think he’s gonna have a Jimmy Carter post-presidency. He’s got a lot of years ahead of him to really do some things. I think that may be the greatest part of his career.

What kinds of questions would you ask? 

One of the big questions would be, how much did you struggle with not being able to directly address the issues and problems of black people on a more thorough basis than you did? I feel like he got brow-beaten—early in his presidency, after Henry Louis Gates was arrested in his house and Obama called the cops stupid, I feel he went into his shell for a while and is now really careful how he talks about race and racism. I would like to know how much of a struggle that was. 

On a recent episode of Ezra Klein’s podcast, you said you don’t really have a plan for this standup tour… So, uh, what can audiences expect? 

Right now, there’s just such a sense of, oh, God. I was trying to fight my way through that feeling and come up with jokes, and that wasn’t working because the jokes were all like, "Why is everything so sad?" So I’ve decided to allow myself to luxuriate in the sadness, and I feel like that’s gonna lead to better results than trying to fight my way through it. It’s too late to make a poster, but that would have been great: “W. Kamau Bell: The Luxuriating in Sadness Tour.” Just a sad look on my face, in a bath filled with bubbles.

And certainly I will have things to say once I get to Portland, because me and Portland have a lot to talk about.

I hesitated to even ask you about Portland, because you’ve already said so much about it—you devoted an entire episode of United Shades of America to this city.

Me and Portland have a new relationship now. I talked onstage about Portland before United Shades of America, but through the show I put Portland on blast, and a lot of people have a lot of feelings about that. That was one of the episodes I heard the most from people about on Twitter. Some people were like, “Absolutely, thank you.” And some people were like, “You got it totally wrong.” And some of the people who said I got it totally wrong were the black people I was trying to help! And I get that—it’s a 42-minute show that talked about a lot of gigantic things and there’s no way to get it all right. I do stand behind what we did, but I certainly understand that I had some very clear opinions about Portland. Now it’s like going back to your ex-girlfriend’s house—like, are we good?

Let’s say you were to do a sequel to that episode. Where would you dig in deeper?

I would like to hear from the black people of Portland who think this is fine, or have reasons for why it’s not fine—who think there’s something Portland has done to black people and think there’s a bigger story there. I would certainly want to hear from black people who feel like I didn’t get it. If we do enough seasons, I’m happy to do reunion episodes of every place we went, even with the Klan. 

And you do have at least one more season coming—the show was recently renewed. What’s next?

I would say the mandate is very clear now: if there are people in the news who are getting the raw end of the deal, we’re gonna try to talk to those people. I think that all you have to do is look at every group that Donald Trump has offended, and we’re gonna try to do an episode about that group. He’s given us a great list of groups to talk to—more than we can get to in one season. That’s the plan.

W. Kamau Bell is at the Aladdin Theater on Friday, October 21.

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