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Randy Rainbow gets real in ‘Playing With Myself’

Now a YouTube star for his satirical musical videos, he writes about how he got there in this entertaining memoir.
Randy Rainbow's memoir is "Playing With Myself."
Randy Rainbow's memoir is "Playing With Myself." [ Dirty Sugar Photography ]
Published Aug. 18

Whatever your political persuasion, someone has probably sent you a link, or several, in recent years to one of Randy Rainbow’s YouTube videos.

“Clang Clang Clang Went Josh Hawley,” “Rudolph the Leaky Reindeer,” “A Spoonful of Clorox,” “Kamala!” — Rainbow’s clever political parodies of show tunes and pop songs, intercut with his sardonic fake interviews with real politicians, draw millions of viewers. He’s been self-producing them for a decade, writing the song lyrics and interview scripts, crafting the wardrobe, wigs and makeup, performing and editing the video, often all within a couple of days.

Where did this guy come from?

Florida, of course.

He’ll tell you all about it in his dishy, funny and sometimes poignant memoir, “Playing With Myself.” Yes, it’s a naughty title — he can’t help himself — but it’s also a reference to his DIY aesthetic and his introverted personality. No, I’m serious, he’s serious, stop that snickering. He can turn on that fabulously gay persona in front of a camera or on stage, but the real Randy Rainbow is more complicated.

First of all, Randy Rainbow really is his name, the one his parents gave him at birth. “My name may seem perfectly on-brand now,” he writes, “but frankly, that’s only because I had no choice but to grow into it!”

When he was born, the Rainbows lived on Long Island. It was a “show-biz positive family” — his father and grandfather were musicians, his great-grandmother a performer in Yiddish theater and the Borscht Belt.

So his folks took it in stride when 8-year-old Randy put on a backyard performance of “Snow White” with himself in the starring role, wearing a pair of pajama pants on his head to represent Snow’s long hair. He got a standing ovation. For 1989, he writes, “this was certainly a progressive audience.”

His doting mom, who is a big presence in this book, signed him up for dance lessons when he was 5 and took him to see “The Nutcracker.” Two years later, he was starring in it as Fritz, the “bratty little brother” with a “fierce pirouette solo.” She also counseled her son about dealing with the bullies at school, who zeroed in on “boys like me.”

When he was 9, his parents’ marriage fractured, and he moved with his mother and her mother, his beloved Nanny, to Cooper City, near Fort Lauderdale. He credits Nanny not only with being his biggest supporter but with being a role model for his comic form. “She always had the TV on at her house, and would walk around talking back to it all day. If a celebrity or politician was being interviewed, she’d respond to the TV as though she were conducting the interview herself. I frequently notice myself mimicking a lot of her style and rhythm in my videos. I’m basically just an old lady talking back to her television set.”

Rainbow writes about coming out as a teenager, which surprised no one in his family but intensified the tension between him and his father, from whom he ended up being estranged.

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He writes about moving to New York to pursue his showbiz dreams, with his own special version of waiting tables while trying to get parts: He did a stint as the only male host at a Hooters at Broadway and 56th Street. He had a blast, but, he writes, “I must have single-handedly depressed more Wall Street stockbrokers than the Crash of 1929.”

Other jobs led more directly to where he wanted to be, and by 2010 he was writing and making videos for Broadway publications and websites. Then the Mel Gibson viral audiotapes hit the fan, with the enraged actor “spewing vile, racist, misogynistic, homophobic, and anti-Semitic rants on phone calls with his former girlfriend.”

A friend suggested Rainbow make a video about Gibson, and he ran with it, deciding to “highlight the absurdity and grotesqueness of the situation by mocking it directly, in character.”

He texted his friend, “I should date him.”

In the first video, he filmed himself walking around his apartment and having a phone conversation with Gibson, intercutting the vile clips with himself asking with “lovey-dovey composure” what Mel wanted for dinner.

It went “viral-ish,” he writes, with 100,000 views — in 2010, amazing numbers. The Gibson videos would launch Rainbow’s career, and, as he writes in a later chapter, come back to bite him 10 years later when trolls took pieces of them out of context as part of an effort to cancel him.

But before that, his career got a much bigger boost, thanks to the 2016 presidential race. As soon as Donald Trump became the GOP nominee, Rainbow’s video “Ya Got Trump Trouble,” based on “Ya Got Trouble” from “The Music Man,” got 5 million views in a day. Within 24 hours of the first debate, he’d posted “Super Callous, Fragile, Egocentric, Braggadocious,” which scored 16 million views.

Rainbow writes that during the Trump administration he felt like the musicians on the Titanic, who “performed in an effort to keep everyone calm.” Then the pandemic hit, a “second iceberg,” bringing his touring show to a halt as his videos attracted an even bigger audience. (His stage show is back in business; he’ll bring The Pink Glasses Tour to Ruth Eckerd Hall in Clearwater this week.)

He writes with pure fanboy joy about the showbiz idols he’s met and become friends with through his work: Stephen Sondheim, Carol Burnett, Patti Lupone. And finally, in 2021, looking for the perfect tune for a video about the “new GOP breakout star,” Marjorie Taylor Greene, he chose “Evergreen.” That video led to a gig creating a video for the release of a new album by his greatest idol, the woman he calls “my lord and savior Barbra Streisand.”

When he reports to his mother that Streisand has texted him — “Dear Randy, Your musical and visual creativity are like buttah!” — Mom responds, “She couldn’t be bothered to pick up the phone?”

Playing With Myself

By Randy Rainbow

St. Martin’s Press, 256 pages, $28.99

If you go

Randy Rainbow’s Pink Glasses Tour plays at 8 p.m. Aug. 26 at Ruth Eckerd Hall, 1111 McMullen Booth Road, Clearwater. Tickets $38.75-$68.75 at rutheckerdhall.com.

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