Randy Rainbow Talks Taking on Donald Trump One Broadway Parody at a Time: 'I'm More Stressed Than Ever'

Courtesy of Varela Media
Randy Rainbow

The political comedian talks parodying the Trump administration through show tunes, his relationship with Stephen Sondheim and his rise to internet stardom.

While many of us make a concerted effort to keep up with the political news cycle, viral star Randy Rainbow has made it his full-time job. In fact, the 37-year-old comedian hasn’t had much of a break from political news since his videos made a major mainstream breakthrough back in the 2016 election.

Rainbow (yes, that is his birth name) spends much of his time researching the news for his web series, where he takes Broadway show tunes and popular songs and transforms them into scathing political satire, usually roasting President Donald Trump. “I try to tell myself, ‘Listen, you're a comedian, you're not CNN,’” he tells Billboard, saying that he tries to manage how much news he actually consumes on a daily basis. “I try to just cover all of the major stuff.”

Randy Rainbow spoke with Billboard about his deep love for Broadway, how he keeps up with the modern news cycle, and the one time he felt truly starstruck.

It's been almost 10 years since you first got started on YouTube. I wanted to know: What was it that made you realize this was the career path for you?

I started out doing musical theater specifically -- I thought I would eventually move to New York and audition for stuff, and maybe wind up on Broadway or something. Well, that didn't happen. I moved to New York in 2003, I was a very young 22-year-old, so I just kind of started finding my way as a human and was working odd jobs here and there. Long story short, I ended up working at a Broadway production office, behind the desk as a receptionist, and I was so bored at that job that I started blogging. [Laughs] I had these interesting things happening to me on a daily basis, like Patti LuPone would walk into the office, or Elaine Stritch would call, so I kind of started blogging about this things, along with my day-to-day life as a gay single in New York. That got a following, especially among the gay and Broadway communities. Once I saw I had a little bit of an audience, the ham in me kind of kicked in, and I said, "Well, let me put myself on camera.” And then, what really started my whole gimmick of inserting myself into hot topics was when my ex-boyfriend Mel Gibson had those horrible audiotapes released. That was kind of my first stab at sketch comedy, and that was my first viral hit. So I stuck with it.

It's very clear that not only did you start making more videos during the 2016 election, but they quickly became viral hits. What was it with everything that was going on at that time that made you make that pivot?

Well, I think there was just really no choice -- of course I saw the spike in numbers, so I followed the audience there. Back when I had a modest following, I would host a weekly show at the bar Therapy here in New York. To get nine people out on a Sunday night was a feat. They weren't turning up all that often. And then when the whole viral thing happened with my videos, I did an Election Eve Eve show at Birdland, the legendary New York jazz club. I showed up, and the place was sold out, and there was a line around the block. I just remember that being a real lightbulb moment. I was like, "Hmm, something has changed here, people know me." So that was really the big moment.

Take me through the process of creating a parody song -- how do you pick the story to tackle, how do you pick the song, how long does it usually take?

Well, it happens very quickly, because we are living in the age of social media. It's gotta be fast, just because of the amount of content being put out, and if you're covering this administration or the news today, the news cycle is completely different by noon the next day. So I am already an anxious person, but this has taken my anxiety to this next level. As rewarding as it has been, I'm more stressed than ever. I constantly have the news on, and I am constantly trying to keep up with things. Sometimes, like this last video I did (“The Donald Trump Cell Block Tango”), that was my third idea, because the news was changing so quickly that I had written about three songs prior. The news changed, so I had to change the video. So it's difficult to keep up.

As far as picking the songs, that's always the easy part for me because I'm very gay -- I think automatically in show tunes, so that always kind of jumps out to me, it's kind of obvious. I also have a nice following now, so people are recommending things that they want to hear, so sometimes I draw from that pool. Then, I try to give myself no longer than 24 to 48 hours to do a video, so I'll write it for about four hours. If it's a song, I'll record for another two or three hours. I'll film for another two or three, and then I'll stay up pretty much all night editing. So it's very fast.

I have to say, your parody of "I Am the Very Model of a Modern Major-General" as "A Very Stable Genius" was just inspired. That was a wild video.

Thank you very much! I was really happy with that one too. Because when I do something like "Desperate Cheeto," which was a parody of "Despacito," that gets like millions of views, because that's a big pop song. But then, with "Very Stable Genius," which is ... oh God who wrote that song?

I think it was Gilbert and Sullivan?

Yes, Gilbert and Sullivan! When that gets as many views, I'm really proud of that, that I can sort of make Gilbert and Sullivan go viral in the 21st century. That's always kind of great.

So it's clear that you do have a very deep love for Broadway. What is it about that art form that really speaks to you and inspires your work?

I mean, musical theater really informed so much of my life. It just so perfectly brings order to chaos, which is why we love theater. Sondheim’s work especially, and musical theater like that, just spoke to me so much and taught me so many lessons. It was always a major part of my life, and I think that's kind of what people connect with, because we are in such a state of chaos now. I think it's just the perfect genre to kind of explain this nonsense that's going on right now, in some weird way.

Do you have a favorite Sondheim show?

I would have to say Into the Woods, and then after that is Sweeney Todd. And actually, if I can brag for just a second, I've become friendly with Steve Sondheim -- you know, I call him Steve, we're buds. I'm looking at a letter on my wall that he sent me, it's right above my letter from Hillary Clinton, excuse me. But I actually have a connection: His husband is actually a dear friend of mine. We met when I was working in that Broadway production office, Richard Frankel Productions; he was Mr. Frankel's assistant. So he's my branding manager and my dear friend. So I've spent a lot of time with Mr. Sondheim, and needless to say, it's been a dream come true.

Well, you get a lot of love and attention from some very famous people, not just Mr. Sondheim. Which celebrity reaction made you the most starstruck when you found out about it?

Just two nights ago, actually, I was doing a show at 54 Below here in the city for Carmen Cusack. I got to do the show Call Me Madam as a part of the Encores! series at the New York City Center, so she asked me to do a song at her solo show. After we did the first show, I was standing at the bar, and someone called me over and said, "There are two fans here who would like to meet you." So I brought my cosmo over to a little booth around the corner, and there sat Steve Martin and Martin Short. Yeah. I really lost my mind, because they are gods to me, really. Like, when I was a kid, Three Amigos was on a loop constantly on my VCR. So, they proceeded to tell me that they were big fans; Steve Martin said I was “major” in his house. He literally started quoting my videos to me, he referenced the "Very Stable Genius" song and said, "We were just watching it in the car on the way over." That's almost too much to fit in my brain, because it was so thrilling.

The most recent political news (at the time of this interview) has Donald Trump declaring a national state of emergency. Does it ever get exhausting, having to stay on top of the news cycle?

Yep, it's a national emergency, so I'm locked in my apartment avoiding the outdoors. [Laughs] But yes, it does. Now, when I started in 2016, before I started touring and my schedule got busier, I had nothing to do but sit around my apartment and make videos constantly. I would really try to cover every single thing that happened. I like to think that the quality and the production of my videos has gone up a little bit. But I no longer put myself in the position of having to cover every single thing that happens, because I simply can't keep up. I try to tell myself, "Listen, you're a comedian, you're not CNN. Calm down." I try to just cover all of the major stuff. Certainly this is one of them. I will be working on a video about the story (watch it below!).  But yeah, I cannot possibly keep up with every single thing.