Randy Rainbow on His Politically Charged Musicals and His Advice for Democratic Candidates

The Randy Rainbow Show_A Very Stable Genius_1_ - Publicity - H 2019
Courtesy of Varela Media

The comedian opens up to The Hollywood Reporter about taking on the Trump administration with his Emmy-nominated YouTube series and why he's excited to have 2020 Dem hopefuls as new targets: "I've nearly had enough of Kellyanne."

Randy Rainbow has never considered himself a particularly political person — but that's changing (sort of). In the nearly three years that have passed since his viral video "Braggadocious" — a biting Mary Poppins-inspired take on Donald Trump's odd choice of vocabulary during a debate with Hillary Clinton — took Rainbow's career to new heights, the comedian has dedicated most of his time to crafting politically charged musical parodies as part of his Emmy-nominated YouTube series, The Randy Rainbow Show. 

"I've been activated by this administration. I'm 'woke,' as the kids say," explains Rainbow, a registered Democrat whose videos typically rack up hundreds of thousands of views each. "I don't have a passion for politics, but I do have a passion for truth and justice. When I see people being attacked as they are now on a daily basis, I respond."

THR spoke with Rainbow (yes, that's his real name) about his colorful internet persona, which has commanded attention from politicians and childhood heroes alike. 

How does your Emmy nomination in the outstanding short form variety series category compare to any other career accomplishment?

It's huge. It's mainstream recognition for the first time, on a level that I've never known before. I'm proud to be included in a category with people like James Corden with Carpool Karaoke and Billy Eichner with Billy on the Street. These are people I admire and who also have large entities and networks behind them. And the fact that I was able to accomplish this from my humble beginnings — and just from my living room and my apartment, essentially — by myself with no team and no network is very validating. It's a huge honor, for sure.

What has been the most unexpected response to your work?

I got a fan letter from Hillary Clinton, which was insane. I heard from Stephen Sondheim, who has become a great supporter of mine. There was no one bigger when I was growing up. He's always been a god to me, so the fact that he's cheering me on is really unbelievable. The coolest part of this whole experience is hearing from my heroes and idols. With each new video, I hear from someone new. For instance, with the "Braggadocious" video, I heard from Dick Van Dyke and that was thrilling. I did a couple of Hamilton parodies and since then I have heard from and become friendly with Lin-Manuel Miranda.

You're about to embark on another leg of your live concert tour. What has it been like adapting your YouTube series for the stage?

It was a pretty natural progression because I started out on the stage and I come from a musical family. My father was always in bands. He played drums and could sing. And my grandfather was a band leader. As a kid, they would throw me onstage. There really was no guesswork here. The fact that I get to tour around the country with my own show, my own band, that I'm greeted in cities that I've never stepped foot in before and there are rooms full of 2,500 people who know my work and are happy to see me — this was always the dream.

Of all your musical parodies, do you have a favorite to perform live?

I do a whole Kellyanne Conway medley. It begins with "Alternative Facts" to the tune of "Jellicle Cats" from Cats. That's a real crowd-pleaser and is always a lot of fun to perform.

You've been uploading videos to YouTube for nearly 10 years. What route do you think The Randy Rainbow Show would have taken if the political climate never became this divisive?

Honestly, I think it would have continued to go in the direction it's going — but it might have taken a little longer. I probably would have continued doing more pop culture, though. Trump's administration certainly gave me a surge of recognition. That was the jumpstart that I needed. Anyone in comedy is seeing a spike in success right now because whenever there is controversy or news like this on a daily basis, comedians benefit. The Daily Show didn't need it and Bill Maher didn't need it — but I did. It catapulted me to the next level.

Though your videos mostly lean left, a portion of your fanbase are Trump-supporting Republicans. When you realized you had conservative viewers, were you at all surprised?

A bit surprised. But then when I think about it, it's really not surprising at all and just a testament to humor and how unifying comedy is, which is something that I've always known. I think it also helps that I'm — for lack of a better expression — not shoving it down anyone's throat. I'm self-deprecating. I try to make myself the butt of the joke and I come from this place of innocence and naivety that isn't threatening to any one side. Again, it's just kind of lightly pointing out, "Isn't this shit crazy?" It's hard to argue with that. 

What is your process when it comes to choosing which news stories to tackle?

With the news cycle the way it is, it's never a problem. I just have to turn on the news and wait for Wolf Blitzer to tell me what song to sing that week. I'm not sitting around waiting for headlines to tackle because there's something new every day. So that's really the easiest part these days.

Do current events ever feel too dark to touch?

Yes, certainly. I'm of the Joan Rivers philosophy where you make a joke out of everything right away. But when we had two mass shootings within the span of 24 hours [in August], I wouldn't really think to go tackle that with comedy. I'd sit that out. So, unfortunately, these days my answer to that question is changing more and more because sometimes it is too much even for comedy to serve as a salve.

As the 2020 election draws near, are you feeling excited or nervous? 

It's going to be nuts. And look, I'm Jewish. I get nervous about everything. I'm still a one-man band and can only keep up at my own pace and cover what I can. So I'm doing my best to not let it get to me. I am excited that there is a new cast of characters to go after a little bit and have as fodder because, let's be real, I've nearly had enough of Kellyanne.

You're a registered Democrat, but Democrats aren't off limits. 

No, everyone is fair game. I've done Barack [Obama] videos and I've done Hillary videos. No one is off limits and there's always something to poke fun at. With Trump, it's been more impactful because there's that basic issue of right and wrong. There's more of a morality thing to combat instead of just lightly poking fun at someone. With this crop of 9,000 Democrats coming, I'm taking copious notes. There's a lot of new material there.

Of the Democratic candidates, whose personality are you drawn to the most?

I think there's something for everybody there. I love Kamala Harris, but she also scares the shit out of me — but in the best way. One of the things that I try to accomplish is creating this character of myself, which is really just a heightened version of myself. Being that character gives me the opportunity to play off of anybody. So even if there's not much meat to one of these guys, I can always still do something fun with them because I can fuel it from my end of the conversation or my character's perspective. That's been a helpful tool. 

Is there anyone you're ready to endorse?

It's too early but, again, I like Kamala. I like Mayor Pete. 

As someone who has gone after Trump, do you have any advice for the Democratic candidate who will go up against him in 2020?

Jeez, I don't know. Unfortunately, they have to go into the gutter with him. I don't know if taking the high road is going to work at this point. The gloves have got to come off, and you've got to go for it. It's not what we want for our country, and I wish that weren't the case, but that's what they've got to do.

If you ever had the chance to meet Trump, what would you say to him?

I wish that I'd be as quick and witty and smart with my responses to him, but I think I would probably just throw up and get nauseous. I hope that I never have the opportunity. I'd rather keep my conversations with Trump on a greenscreen and not in real life.

What's next for you?

I would love to expand this video series into a TV show — maybe do a weekly half-hour. I'm not exactly sure what the format would be, but something on Netflix or HBO. In my imagination, I see a hybrid of Pee-wee's Playhouse and The Daily Show, tackling everything from politics to pop culture. That's something I'm certainly secreting right now. Hopefully, we're a little closer to that than we've ever been before. I'm also hoping to bring the live show to the next level and make it more of a spectacle. And, who knows, maybe have a Broadway run or something? There's lots of ways it all could go, and I'll be happy with all of them.

Interview edited for length and clarity.

A version of this story first appeared in an August stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.