Randy Rainbow, YouTube’s Musical-Satire Assassin

His self-deprecating takedowns can neutralize haters before they even know what hit them.

In his scalding, blistering, singe-your-eyeballs-just-by-even-looking-at-it takedown of Education Secretary and plutocrat Betsy DeVos’ attempt to gut the Special Olympics of federal funding, musical satirist Randy Rainbow parodied the song “Cruella De Vil” from the original 101 Dalmatians. But for the bridge, where the original, Grinch-y lyrics scan, “You come to realize you’ve seen her kind of eyes / Watching you from underneath a rock,” Rainbow sings “She bathes in teachers’ tears / And burns up school supplies to fuel her yachts,” deliberately lisping the last S to hammer home the point that DeVos does in fact own more than one very large pleasure craft.

He hath damned her with sibilance, in other words.

Rainbow — his actual name — does several things well. He’s a puckish lyricist, a foil for Washingtonian chicanery, a video editor with the technical skills and bonkers sensibility of a digital native, and a rubber-faced queen whose expressive eyes launch zingers of their own. He doesn’t have resting bitch face so much as a malevolent smile; the more teeth he’s flashing, the worse you know it’s going to hurt. And, of course, he sings, usually backing himself up in quadruplicate.

“I’m not a political pundit by any means,” Rainbow tells SF Weekly by phone. “If I have a passion for anything, it’s more the truth than politics, and I think that’s what got me interested in comedy in the first place, because the best comedy is the truth. People recognize that.

“I also try to make myself the butt of the joke as much as possible, so that might be endearing to people on both sides.”

Rainbow, who plays both the Luther Burbank Center for the Arts (Thursday, April 18) and San Francisco’s Masonic Center (Saturday, April 20), has little difficulty translating these four-minute clips to the stage. He has a big screen behind him onto which the “greatest hits” are projected, and a band that enables him to segue from video clips to songs, plus there’s a Q&A component with audience participation.

That would seem a little risky, a flamboyant performer presenting heavily doctored footage meant to lampoon the Establishment, sometimes in the form of “Border Lies” (set to Madonna’s “Borderline”). But there aren’t that many MAGA hecklers, he says.

“As far as the live shows, I’ve only had like two walkouts, which — you gotta think — for as many shows as I’ve done, is pretty good. A lot of the mail that I get is people saying, ‘I don’t agree with you and we don’t share any of the same beliefs politically, or in any capacity, but I love your videos.’ ”

While he also confesses to being extremely thin-skinned — “I would never process criticism,” he admits — the use of self-deprecation can really inoculate a crowd. Rainbow is steeped in the culture of musical theater, so much so that his last day job was as a receptionist for the accounting firm that processes Broadway shows and tours. And now that he himself is touring in short bursts, it’s become a little tougher to get more than two or three videos up per month.

“It’s still just me, doing everything from writing to recording to editing, which is very time-consuming,” he says. “I luckily just go out in clusters on my tour, so I’m never gone for more than five or seven days, tops, and then I come home for a week or two and turn on CNN to see whatever Wolf Blitzer tells me to sing about that night.”

If Netflix wanted to give him a show and a team of writers and producers, he’d jump, but for now he does everything in his apartment. Upon selecting a topic, he’ll write for four hours, record for two or three, film it for another two to three, then stay up all night editing — which can take up to 15 hours. The result is pieces like “He’s in Love (And We’re All Gonna Die),” a spoof of the Donald Trump-Kim Jong-un bromance by way of “Wonderful Guy” from South Pacific.

“I’m not a disciplined person. I manage to whip myself into shape enough to get into this routine, but I would die if I did that every single night,” he says.

Rainbow uses props he gets from his costume designer — Amazon Prime — the best-known of which is a pair of cheap, pink, plastic glasses he dons when he’s about to read someone. (People started wearing them to his shows, so he branded his own and sells them as merch.) They’re reminiscent of talk-show host Sally Jessy Raphael’s red glasses, which were so much a part of her look that after she stopped wearing them people ceased to recognize her.

“I actually heard from Sally Jessy, who I’m proud to say is a fan as well,” he says. “She took note of the glasses and so we kind of have that sisterhood between us. … I like to say they kind of became my pussy hat.”

After joining Carmen Cusack of Bright Star fame on stage for a song at New York’s cabaret club 54 Below, he remained there as she took her bows, thanking Steve Martin and Martin Short, who happened to be in the audience. Rainbow says he “lost my shit” when he heard those words.

“People think I’m obnoxious and outspoken, but I’m actually very shy, especially when it comes to people like that,” he says. “They actually sent somebody over and requested that I join them for a drink, and it turns out they’re both big fans. Steve Martin was quoting my videos to me and telling me I’m a big deal in his house, and it doesn’t fit in my brain. He was asking specific questions about specific videos!”

Fame doesn’t seem to have changed him much. It was “Braggadocious,” the anti-Trump parody of “Supercalifragilisticexpialidocious,” that propelled Rainbow to YouTube stardom in the run-up to the 2016 election. So The New York Times devoted its occasionally unbearable “Sunday Routine” segment to Rainbow the weekend before the midterms. Rather than purport to arise at 6 a.m. and consume a single calorie before working out all morning and volunteering for Oxfam until the wee hours, he admits to lounging about, not particularly enjoying the gym much, and letting brunch with friends transition seamlessly into cocktail time.

“I could have bullshitted everyone, but what for?” he says. “Who am I fooling? I was already self-conscious about it because I thought it featured a lot of drinking, but whatever.”

It’s just fuel for the late nights feverishly editing a litany of scandals and national embarrassments into a devastating reworking of “My Favorite Things,” covfefe and all.

Randy Rainbow, Saturday, April 20, 7 p.m., at the Masonic, 1111 California Ave. $45; sfmasonic.com

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