“The first time I sang [a song about depression] was the first time I saw someone cry at a show,” says Kilstein, 33. “I thought, ‘Well f**k, this is sort of what I always wanted to do with comedy but I could never do it.'”

A couple of years ago, the D.C.-born performer — who co-hosts the popular progressive podcast Citizen Radio and has appeared on The Conan O’Brien Show and Countdown With Keith Olbermann — opted to take his ranty act in a more musical direction. The change was prompted by a difficult time in his life: the death of his friend and mentor Robin Williams.

“[Williams] helped get me sober,” Kilstein says of the late comedy legend, who took his own life in 2014.

A few years ago, Williams appeared at one of Kilstein’s gigs in San Francisco, and wound up chatting with him backstage. They became friends. Williams would later help Kilstein book gigs and even fund his podcast.

“Robin didn’t really influence me comedically, but more as a person,” Kilstein says. “I think it’s almost cooler when they can inspire you to be a better person.”

After Williams’ death, Kilstein considered quitting comedy. But he ultimately decided that Williams wouldn’t have wanted that. So the performer evolved instead. Now, he takes on the same heated subjects he always has — like rape culture, male privilege, religion, drones and gay marriage — but puts it to music with his band, Jamie Kilstein and The Agenda.

Kilstein plans to release a new album of these musical rants early next year.

Warning: Explicit language.

“It’s by far what I’m most proud of. I said everything I wanted to say, I defended causes I really care about,” Kilstein says of the album. His new material doesn’t shy away from big issues, including adoption for same-sex couples, feminism and Islamophobia.

“The good news is that I’m not really a man of metaphors, so you can pretty much tell what the album is going to be about by the track listing,” Kilstein says. “For example, the first song is called ‘F**k the NRA,’ so it’s pretty clear what that’s about.”

But when he appears tonight at Tropicalia in D.C., Kilstein won’t only stick to politics.

“I thought I used to be so edgy screaming, ‘F**k the church,'” he says. “But to me now it’s arguably more important to be onstage saying, ‘It’s OK to take care of yourself, or feel sad.'”

Jamie Kilstein performs tonight at Tropicalia. His forthcoming album is available for preorder.