The singer-songwriter found the reaction of many to George Floyd's murder as a sign that a "broad awakening" is happening in America.
"I think everybody should be doing more," he said. "It's time for me to listen. And it's time for other folks to listen."
Listening to other perspectives and learning about other peoples' fears shook the "Tennessee Whiskey" singer's views on society to their core.
"You know, I thought we were living in a different country. And that's 100% real," he said. "I feel like the country that I thought that we were living in was a myth."
When asked to comment on Black Lives Matter, Stapleton mirrored common sense takes by Dolly Parton and other outspoken country stars: "Do I think Black lives matter? Absolutely...I don't know how you could think they don't.
"I think we all have a lot of work to do, you know, as individuals and as a society," Stapleton added. "And if you don't think that, I think you're not looking."
"I don't have any regrets about saying anything that I said. But I'm a human being, it hurts if somebody wants me to go to Hell," he told the Los Angeles Times (as quoted by Whiskey Riff).
He copes with such ugliness by keeping social media, and trolls in particular, in the right perspective.
"Look, you're talking about a very small percentage of people that listen to my music," Stapleton says. "And some of those people aren't even people, they're robots. I don't mean that as a metaphor. They're actual bots meant to modify our behavior.
"I think it's important that we live in reality and not in that social-media space, where the most hateful voices get the loudest megaphone," he adds. "But I feel sorry for people that think anything I said was offensive. I'm sorry they lack the capacity to approach things as human beings."
Stapleton's new album Starting Over, completed shortly before the coronavirus (COVID-19) pandemic shut down the tour plans of his Nashville peers, follows the commercial and critical success of Traveller and the two-part From A Room series of solo albums.
Its track list includes "Watch You Burn," a song about the 2017 mass shooting at a country music festival in Las Vegas.
"It's a powerful number to me that conveys the sentiment, 'hey let's cut the evil s*** out'... It's a plea in some ways," he told CBS This Morning of the "therapeutic" song.
Once touring on his new songs makes sense, Stapleton hopes the road beyond livestream specials and drive-in theater concerts goes on forever.
"We all hope for that Willie Nelson career where we're, you know, 85 or 86, and we can go play as much as or as little as we want to," he told CBS This Morning. "I think if I am able to walk out on stage and hold a guitar when I'm 85, I think that's probably gonna happen."