Out Emmy- and Grammy-nominated performer Randy Rainbow is reflecting on his life with a new book titled Low-Hanging Fruit: Sparkling Whines, Champagne Problems, and Pressing Issues from My Gay Agenda. This follows his previous New York Times bestseller Playing With Myself, a memoir from 2022.
He became a viral sensation by creating music and videos for his popular web series The Randy Rainbow Show. His debut solo album A Little Brains, A Little Talent had him singing with Schmigadoon!’s Tituss Burgess for “Bosom Buddies,” and featured legendary performer Bernadette Peters for “My Best Girl/It Only Takes a Moment.”
His political satire seems to never run dry, and his fake phone calls continued to crack up listeners. Rainbow arrives in the Windy City for the Chicago Humanities Festival this October and talks about the upcoming book appearance before hitting the road.
Windy City Times: Thanks for fitting me into your gay agenda today, Randy Stewart Rainbow!
Randy Rainbow: My full name? Did you talk to my mother?
WCT: Not yet. You should bring her to Chicago on this upcoming trip.
RR: She would go anywhere for free to stay in a hotel. She is not coming to Chicago, but she will be at the New York and Palm Desert stops on the book tour. She will make it there eventually.
WCT: When did you first learn that your videos were valuable while going viral?
RR: My first book takes people through that journey, but long story short, I was a frustrated performer working in an accounting office as a receptionist in my twenties, and started a blog. That led to comedic videos where I would take hot topics and entertainment. When I made the video “Randy Rainbow Is Dating Mel Gibson” and started plugging myself into the headlines, it went viral. I kept going until 2016 when things shifted into politics. It took off from there.
I keep waiting to go back to Mel Gibson, but I am stuck with the elections
WCT: I just watched the “JD, JD…(Married Lady)” video. Is it time-consuming to edit videos like that one?
RR: The editing is my favorite part and the most fun; takes about a day or two. I have a music team now, so the tracks are no longer karaoke like they were in the olden days. We get together and create the tracks from scratch with vocal arrangements. These days I give myself two weeks to put together a video.
WCT: The Fruit book cover is purple and you were wearing purple today. Is that your favorite color?
RR: That’s a coincidence. Blue is my favorite color but pink and purple are a brand staple.
WCT: Why did you choose Low-Hanging Fruit as a title?
RR: For a number of reasons, but I thought it was a funny, slightly provocative title and a little self-deprecating. It is about all of the stuff that is low-hanging around my brain these days. It’s a fruit cocktail of topics that I give my humorous take on, such as social media and Amazon customer service calls.
WCT: The beginning section has you venting about the train system.
RR: It starts off with a letter of resignation to stupid people. This book was cathartic and released me from trying to fix stupid people. I guess that’s a little judgmental, but I can be.
WCT: You also write personal stories throughout the book. How is your mom with having her conversations printed in the book?
RR: She insisted. We did that in the first book and it was such a hit that my editor said to do it again. I think it’s even funnier this time out.
It was written with the audiobook in mind and produced like an old radio variety hour, so there are sound effects, special guests and music. My mother makes an appearance and reads her part.
WCT: Who is another special guest?
RR: One is my cat and she reviews me on Yelp.com about her experience of living with me. She’s voiced by Pamela Adlon from King of the Hill.
WCT: When you mention a celebrity such as Jacob Elordi, do you have to ask permission to use his name in a book?
RR: No. There are lawyers to tell me what I can or can’t write about. I am allowed to write about Jacob all I want, and didn’t say anything bad about him. I did that because of my body envy and Jacob Elordi was the target.
WCT: You have Zachary Quinto in your phone contacts?
RR: Yes. In the book, I go through a list of celebrities that I have in my phone like Zachary and Dana Bash.
WCT: Was there a part of the book that wound up on the cutting room floor?
RR: Not that I can think of. I wrote this while I was on tour and down to the wire for my deadline. All of the things I wanted to talk about worked out perfectly to be the exact number of pages I needed for this book.
I finished my tour and the book right on time, so there was no time for anything extra.
WCT: I attended The Pink Glasses touring show in 2021 at the Chicago Theatre and noticed a lot of straight people there.
RR: My demographic is very eclectic, which I didn’t really appreciate until I started doing the live shows. It’s kids age 8 all the way up to senior citizens with straight people, gay people and everything in between.
WCT: How do you navigate political comedy when out in the world?
RR: These days it’s easy because there’s so much material. I just turn on the TV and wait for Wolf Blitzer to tell me what to sing about.
WCT: Do you have a favorite musical of all time?
RR: I have many so we could be here all day, but Into the Woods and Sweeney Todd are my top two. I love Wicked, Les Miserable and many more. I am looking at my wall with a huge amount of window cards.
WCT: You make a joke in the book about a musical version of the movie Don’t Tell Mom the Babysitter’s Dead. What are your thoughts on these nostalgic movies being turned into musicals like Back to the Future and Beetlejuice?
RR: There’s a snobby part of me that is high-brow and longs for original works. While I can be judgmental, some of them are really fun. Don’t Tell Mom the Babysitter’s Dead is one I made up to make a point in the book, but I am sure it is on its way!
What I am looking forward to is Death Becomes Her. It started in Chicago. Did you see it?
WCT: Yes, Megan Hilty was a force and carried it on her shoulders.
RR: I love her and Jennifer Simard. I am excited!
WCT: There’s a gay man playing a straight role in the musical too.
RR: My friend Chris Sieber.
WCT: You must watch musicals all the time since you live in New York. Are you going to see Oh, Mary!?
RR: I am, and I grew up with Cole Escola so I can’t wait to see it. I am way behind I am embarrassed to say. The last one was Ethel Merman in Annie Get Your Gun!
I am so busy with this book tour and making videos for this next election, but once I return in October I will see everything!
WCT: If Low-Hanging Fruit was made into a movie who would play you?
RR: Me! I hope my agents can at least swing that. Do you think I have aged out?
WCT: Not at all. What are your current thoughts on your past tweets that don’t read well today?
RR: I write about those at length in my first book. Comedy is not evergreen and is always changing. People are still experimenting and being successful with edgy comedy like that. It is not my brand anymore. I never want to offend anybody. That brings me no joy.
I am of the mind if you can make it work and make people laugh in a way that is smart and funny, that’s good. One of my comedy heroes Joan Rivers described comedy performances as little mini vacations from life, so I try to gift that to people.
This speaks to us as to where we are as a society and unfortunately, a lot more is off the table comedically than a few years ago. I tend to think the worse off we are in real life, the less people want to laugh about it. It’s still part of my schtick to take things that are sensitive or polarizing to shed light on the darkness in some way, whether it be Donald Trump or the pandemic. I try to add levity to it and it is not always easy.
WCT: Covid was still hanging around when you were last in town. This time out you can possibly go to Sidetrack where they play your videos. Have you heard of it before?
RR: Is that where they play show tunes?
WCT: Yes, and I am sure they will play your videos if you pop in for a visit.
RR: This is a book tour, so I don’t have to sing. I can enjoy myself in each city, so I would love to go.
WCT: Well, I hope when you arrive that your Grindr account is full of fans welcoming you to our fair city as you mentioned in the book.
RR: Me too. I will accept a dick pic or two. Listen, I am not above it…
WCT: Who is the moderator for you at the Harris?
RR: I know Harvey Fierstein is doing it in New York, but I don’t know about everywhere else yet, stay tuned!
Follow the Rainbow to the Harris Theater, 205 E. Randolph St., on Oct. 16 at 8:30 p.m. Tickets can be found at chicagohumanities.org and the moderator is now scheduled to be Axios reporter Justin Kaufmann.