Try to imagine the kind of person whose career has skyrocketed since the appearance of Donald Trump on the political scene, and a gay show tunes singer might not be the first to spring to mind. But Randy Rainbow’s satirical viral videos, skewering the Trump administration and the GOP, have found a whole new audience—and some gift-wrapped material—through our current president. From "Desparate Cheeto"—sung with some impressive vocal range to the tune of "Despacito"—to “Braggadocious,” his videos have racked up millions of views. Now he’s taking his particular brand of satirical show tunes on the road, with two upcoming Portland shows at the Aladdin Theate.r We caught up with him to find out about the carousel of crazy, accidental activism, and his fan mail from Hillary Clinton.  

How was the viral video star Randy Rainbow born?

Randy Rainbow was my real name, believe it or not! It could have gone another way, and I could have been a straight accountant. But there was really no choice for me. I have a musical theater background, so I started on the stage. About eight years ago, I was taking a break from that, developing my comedy voice. I had my own blog, and that eventually led to turning the blog posts into videos. My first viral video was “Randy Rainbow Is Dating Mel Gibson.” That got me some notoriety, which led to a steady gig with broadwayworld.com. I started covering things for the theater world, and it just seemed like an obvious thing to incorporate music. So I started doing musical theater song parodies, all the while still doing my own videos, and one day I just got confused, blended the two together and did something political and musical at the same time, and it worked! And I’ve been doing that ever since. Kind of on accident!

I can’t imagine it’s hard to find material, but do you have to pay constant attention to the news cycle to keep up?

It’s easy nowadays because there’s something happening very single day. Almost three times a day there’s breaking news and it’s always crazy and worthy of parody. It’s a little bit of a challenge to keep up with everything because I’m on tour. For instance, I was just on tour for this last week, and now that I’m home, I’ll see what’s trending. I’ll jump on the carousel of crazy, and see where we end up. There’s never a slow news day, I don’t have to tell you that.

Does it feel strange that what many argue is the country’s political nadir has had such a positive impact on your own career trajectory? Donald Trump has really helped further your career, in a way.

It’s strange, I guess. But anyone doing comedy is thriving right now. The real reason for comedy is to make us feel better—it gives us something to laugh at in the face of this nightmare that we’re going through.

Do you ever wonder what you’d be doing if Hillary had won?

There’d be plenty to make fun of if Hillary had won! But I might be able to sleep a little bit more because I don’t think it would be quite as insane as it is now. By the way, Hillary is a big fan—she did send me a fan letter. I have it signed and hanging up!

I heard you get appreciative letters even from non-liberals. Is it true you have some Republican fans out there?

You’d be surprised by how much hate mail I don’t get. I get emails all the time from people saying, I don’t share your views, I’m on the other side, and I hate gay people and I’m racist and I’m a horrible person, but I love your videos! Not quite to that extent, but that’s how I read it. I think it’s just testament to how unifying comedy can be that there are people on the other side, as it were, who do have a sense of humor about what’s going on. A lot of them!

It may be laugh-out-loud funny, but satire can also have a political impact and serve serious ends. Is that part of why you do what you do?

At shows, I see how much of an impact it has on people. I’ve kind of become an accidental activist. I never really set out to do that. I have my opinions, but my intention is always before anything to just entertain and be amusing, so the fact that it does have the power to impact people and change minds even a little bit has been a very incredible byproduct of all this.

Should we hold our breath for a Randy 2020 presidential bid?

Probably. I think that’s probably the next step. I’ll tour with my musical show and then I’ll take the White House. But I don’t think you want me in politics. I think I’m better off in show tunes. Although it wouldn’t be much worse than what we’ve got right now.

Tell us what we can expect from the live show.

It’s really about the music. I’m so happy that I have all these viral song parody videos. I have a full band and there’s backup videos I interact with and that segue into live versions of the musical parodies. It’s Randy Rainbow in concert, my dream job!

Randy Rainbow Live

7:30 and 10 p.m. Fri, Apr 27, Aladdin Theater, $37.50