book club

Last laugh: Randy Rainbow on bullies, Trump, and the power of comedy

Randy Rainbow
Randy Rainbow. Photo by Dirty Sugar Photography

On the surface, it seems that Randy Rainbow (yes, that is the actual name on his birth certificate) was an overnight sensation. With more than 100 videos lambasting the ridiculous nature of politics, the comedian guided us with hilarity through a pandemic lockdown and presidential pandemonium. Yet it took the Long Island, New York, native years to achieve notoriety beyond the LGBTQ community. Twelve years ago, he posted his first video, Randy Rainbow is Dating Mel Gibson, which became a viral sensation.

Rainbow’s latest creative endeavor, the memoir Playing with Myself (St. Martin’s Press), chronicles his childhood (including a backyard staging of Snow White with Rainbow in the title role), family dynamics, and his New York career, which has included a job at Hooters. While still awaiting his invitation to the White House, Queerty spoke to the funny man about the book and how he balances his authentic self with his on-screen persona.

What prompted you to say, “Hey, I want to put my life story in a book.” What was the inspiration behind that?

Well, simply because they asked. I had been approached by a few publishers to write books over the years, but they suggested more novelty comedy books, like a jokey Trump book or a coffee table book. Somebody asked me if I wanted to write a book about my love of Andrew Cuomo. Thankfully, I turned that down! St. Martin’s Press ended up being the ones that we chose because we thought they were the best fit. Ultimately, they were interested in my personal story.

I thought it was a great opportunity because people through the years have been so generous with their gratitude. I hear “thank you” so much more than I ever thought I would. People are nice enough to say that I’m the guy who got them through the pandemic, Trump, and even through personal struggles in their own lives — and that’s really just a testament to the power of comedy and how healing it can be. Musical comedy, especially, if you ask me.

But I realized that these people who were being so generous with their own stories didn’t really know who they were talking to. They didn’t really know me because they’ve come only to know this two-dimensional persona, which is certainly a part of me, but nevertheless, it’s scripted and campy and heightened. So, I thought this was a great opportunity to come out and formally introduce myself once and for all, which I was happy to do.

Randy Rainbow

After the book went to print, did you think to yourself, “Oh!  Should I should have talked about this or that?”  Was there any unfinished business you left unwritten?

Well, with me … I’m a lunatic. You can ask the people at St. Martin’s. To the wire, I was sending them edits and updates. So yeah, I would continue to rewrite things and work on things to the last second. But for the most part, I am happy with the finished product since this was my first book, my first time kind of “coming out” and being this honest and real.

You write about the strained relationship with your father. Was that painful or more cathartic?

It was both. It was certainly cathartic, but humor is my savior every time. It really helped to have the Donald Trump angle because my father was Donald Trump, in many ways. I felt like I could be humorous while also being very serious about this man who was a dark cloud in my home and childhood and who was verbally and emotionally abusive to my mother and me. I could also then diffuse that with a joke.

I also found it interesting that, for anyone who followed my career who got to know me as Trump’s on-screen nemesis — at least on social media — I had this Star Wars-like revelation of “Luke, I am your father.” To know that Randy Rainbow is the guy who grew up, essentially, with Donald Trump in his living room. I am the spawn of a Donald Trump clone. So as much as it was cathartic and put down on paper, I also thought it was interesting to write.

Do you ever wonder if your father hadn’t been so tough to deal with whether you would still have followed comedy, or was that an escape for you?

I probably would have been funny anyway because I was the fat effeminate kid on the playground who had to contend with lots of schoolyard bullies, and that always brings out the funny. My family is also hilarious. I’m really the product of my grandmother, who is in the book and was really my greatest comedy muse. I learned her philosophy on life, which was to find the funny in everything and laugh immediately.

You wrote about your issues with cancel culture and the controversy you faced surrounding it. Do you think it’s a comedian’s responsibility to apologize? Is there a line too far to cross? Or is it the role of comedians to say, “Listen, we’re just putting this out there to cope and just get through?

I don’t have to tell you that it’s a very nuanced discussion and quite subjective. I don’t know if I can really comment on every comedian’s responsibility, but I think it’s important that those comedians are truthful and they’re doing material that they believe in. I personally enjoy growing with the times, I like learning and adapting. So it’s tricky.

That part of the book is not a 15-page mea culpa, but I described it as a humbling experience, it was educational, and I took from the experience what I did. But I also never want to discourage risk-taking in comedy. I’ve heard from people in the worst crises. People dealing with the worst things you could imagine. And the reason I’ve been able to get those laughs and reach those people through humor was because I was taking some kind of risk. So, it’s a tough discussion, especially now, because the line is moving so rapidly, and things that we’re saying in this interview might, 10 years from now, be completely off-limits. So it’s hard to keep up.

Randy Rainbow
Randy Rainbow. Photo by Dirty Sugar Photography

You wrote that you heard personally from Hillary.

Oh … Clinton, you mean?

Yes (laughs) that one.  Have you heard from any other politicians or their offices concerning your comedy?

I’ve heard from some senators and candidates over the years. I heard from Marianne Williamson’s office. They wanted me to do something with their campaign, if memory serves. Joe and Kamala have yet to reach out, and I haven’t been invited to the White House or stayed in the Lincoln Suite just yet. I don’t know what’s keeping them!

Related: Who is Marianne Williamson and why should LGBTQ people care?

I became friends with some of the Trump folks after the fact. For example, I’m now friends with Anthony Scaramucci. I heard from whistleblowers within the Trump administration that I had fans in the White House during his presidency. I assume they mean Melania, but I’ll never know.

What have been some of your biggest rewards from your fame and what have been the biggest challenges?

The rewards are the connections that I’ve made both with my audience, who have expressed so much gratitude. It has really given purpose to what I do and has inspired me to go forward. I’m not where I was in my 20s when I was just looking to get a laugh or to get eyeballs on me and make a scene. Now I feel a responsibility to make a substantial contribution to the world. Especially If I’m putting myself out there and have the nerve to stand on a stage with the platform I’m fortunate to have. So, that’s been nice. Also, you know, there’s no shortage of celebrity name-dropping in my book, but it’s not gratuitous. I talk a lot about the people who inspired me, from Stephen Sondheim to Carol Burnett. They have now come into my life and have been support systems through all of it. So that, to me, has been the dreamiest, most exciting, and gratifying part.

And some of the challenges?

I’m really a very introverted, shy person. Well, not after a couple of drinks. I mean, I’m pretty complex, and there are many sides to me. The character version of me that people see on screen is definitely a part of me — an authentic genuine part of me — but I’m also withdrawn at times. I don’t like the spotlight on me a lot of the time. I like to just be to myself, so having a new kind of brighter spotlight on oneself does make me a little nervous and brings some agita, but I guess that’s what they call champagne problems.

I think that it’s common for many comedians to be very introverted. Because people have this expectation that you have to be funny all the time. You’re correct to suggest that life can be endured with comedy, but there are those moments you don’t always want to be “on.

It can be a bit of an identity crisis and rough on one’s soul when you’re not feeling like putting on a show. But you do the meet-and-greets with a room full of thousands of people expecting that, so you’re obligated to give them what they came for. But it’s been challenging to find the balance of giving people what they want but also being authentic to myself. At the end of the day, people want you to be authentic because that’s what resonates with them. They don’t want you to be phony-baloney all the time. So, I’m hoping this book and this podcast that I’m doing will introduce a little more of the genuine non-scripted, non “on all the time” version of myself.

Tell us more about the podcast.

It’s going to be kind of variety. There will be scripted sketch stuff with persona Randy doing crazy, ludicrous things, like having phone conversations with people who are not really there. But I also will be having real conversations with some of my most interesting, wonderful friends. We just put a few of them in the can.  I had some great talks with Josh Gad, Titus Burgess, Sean Hayes, Carol Burnett and Harvey Firestein. So, I’m excited for people to hear those conversations.

Related: Stop what you’re doing and watch Tituss Burges sing ‘Here’s to Life’

You went to school with Josh Gad, right?

I went to theater camp with him when we were teenagers. I taught him everything he knows.

I have no doubt. If you hadn’t packed up and moved with your friends to New York, what do you think would have been your career. Do you ever wonder, “Gee, I’d really like to be a “fill in the blank”?

I don’t know. I’ve never made goals for myself, and that’s probably to my detriment and benefit, I guess.  When I was a young, green comedian trying to figure out my angle, my voice, and what my schtick was going to be, that’s when you stumble and fall down a lot. Ultimately, my biggest success was just relaxing into doing the stuff that I love — the things for which I have passion and joy — which is basically what I’m doing now.

When people see those videos, it’s just me dressing up and having a marvelous time doing stuff that I wouldn’t normally get the opportunity to do in any mainstream professional world. So that just came from me ultimately, just doing what brings me joy. That’s what I’m going to try to do as much as possible for the rest of my days.

And what’s next for you artistically besides your podcast? I know there’s a hint of a possible Broadway show.

It comes as no surprise to say that it would be a dream come true. I’m not at liberty to say too much about it, but we are talking to some Broadway producers. I’m hoping maybe something will happen in 2024, which will obviously be a contentious election year. I’m sure there will be lots of material. I’m afraid to even think of what kind of material. Marc Shaiman and I wrote a song called “Randy Rainbow for President,” which is on my new album. So, I’m thinking maybe that could be the title track to the show or maybe an 11 o’clock number.

Well, Joe and Kamala will have to get the guest bedroom ready at that point because you will get your invite.

If I’m on Broadway, I damn well better be invited to that f*ckin’ bedroom!


Randy Rainbow is currently on a book tour, followed by concert dates through September 2022.

Ryan Leeds is a freelance theater, food, and nightlife journalist who lives in Manhattan. He is the Chief Theater Critic for Manhattan Digest and has contributed to EDGE Media Network, The Broadway Blog, Dramatics, Teaching Theatre, and Howlround.  Follow him on TwitterFacebook, or Instagram.

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