Why Stephen Colbert Asked a Black Lives Matter Activist to Take Over His Show

"Is there anything you'd like to ask me about being white?"

It's a question talk-show hosts rarely, if ever, pose to their guests. Yet Stephen Colbert asked it of Black Lives Matter activist DeRay McKesson during a segment of the Late Show on Monday night.

Colbert sat in the blue armchair typically reserved for his guests, while McKesson occupied the seat behind the wooden desk where Colbert typically grills his subjects—from Atlanta rapper Killer Mike to Pakistani human rights activist Malala Yousafzai. The role-playing scenario was proposed by Colbert as a playful exercise in recognizing and surrendering his white privilege. After all, as McKesson pointed out, what is privilege if not having a television show, wealth, and access?

The duo discussed McKesson's involvement in Black Lives Matter and his Campaign Zero initiative, a convention and online platform aimed at curbing police violence in America. When McKesson asked Colbert, "Why do you think white people are uncomfortable talking about race?" the dialogue that followed touched not only on privilege but also on guilt.

"I feel guilty for anyone who does not have the things I have," Colbert admitted. "That includes black people or anyone because I am so blessed that I think there's always the fear that it will be taken from me."

McKesson wasn't wrong to assume that this kind of conversation makes some people squeamish. A survey conducted by MTV last year found that nearly half of respondents 18 to 24 said they thought it was wrong to draw attention to another person's race, even if the commentary was generally positive. A majority said it was tough to have a respectful conversation about bias in person or online—let alone in front of a live audience and on national television.

But for McKesson, the 30-year-old named by Fortune last year as one of the world's greatest leaders, engaging in these sometimes awkward conversations is imperative to creating progress toward racial equality. "I think that people are uncomfortable talking about the racist history of this country and what we need to do to undo the impact of racism," he told Colbert. "People just like to act like we don't have a legacy of racism here, so I think people get really uncomfortable with it. But we know that we can't change it unless we address it, right?"

As one of the most prominent voices in the Black Lives Matter movement—and an influential social media personality with hundreds of thousands of Twitter followers—McKesson has attempted to do just that. A member of the grassroots group We the Protesters, McKesson helped organize protests and demonstrations after the police-involved deaths of Michael Brown in Ferguson, Missouri, and Freddie Gray in Baltimore.

His latest project, Campaign Zero, launched with other Black Lives Matter organizers, is a "10-point platform to end police violence," he told Colbert. The initiative seeks to achieve its goal by focusing on issues at all levels of government and law enforcement, including community oversight, body cameras, better police training, police union contracts, and community representation. The campaign page includes a set of federal, state, and local policy agendas and a score card that assesses six leading presidential candidates' stances on each of these issues.

"What we've seen is that across the country, these issues around police violence in communities of color have just been popping up," McKesson said, referring to the deaths of Brown, Tamir Rice, and Sandra Bland. "Across the country this has been so similar that we know it's not these isolated events, that it is actually a systemic problem."