Randy Rainbow’s Witty World

How a musical theater nerd reinvented political satire for the YouTube age
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Photos by Marvin Joseph

Randy Rainbow stands before the full-length mirror in the living room of his compact Queens walk-up, oozing mischievous charm. He tugs on a black sequined jacket, checks his satin tie and adjusts the angle of his bowler hat.

Maneuvering around a huge backdrop set up in the room, he’s trying on a variety of costumes for a photo shoot for this article. He glances into an open suitcase of props that he keeps in the next room, his home office. Permanently hoisted there is a green screen, along with a camera on a tripod and four MacBook Air laptops. A few hours after the photographer and I leave, Rainbow will step before the camera and belt out some just-written lyrics describing the despicable, dastardly or just plain dumb behavior of today’s prominent political figures.

But first, with a practiced swipe, he applies his Rouge Dior lipstick, a gift from “Little House on the Prairie” star Melissa Gilbert, a fan who messaged him on Twitter and showed up at his birthday party in July with a bag of cosmetics from Sephora. “This girl knows me,” Rainbow observes.

He patiently strikes multiple funny poses and doesn’t object when I pick up his Persian cat, Mushi, who protests with a meow. We are clearly invading their space, but Rainbow just turns on a sweet megawatt smile like the show business pro he is. “Let’s try the devil horns,” he suggests enthusiastically, digging into his prop suitcase. “It’s Sa-tan!” he warbles in his stage-worthy tenor as he affixes the red horns to his head.

In a topsy-turvy era, is it surprising that a political commentator should dress in sequins, feather boas and pink cat-eye glasses? Because that’s Randy Rainbow (yes, it’s his given name). In real life, the 37-year-old leads a solitary existence in an orderly apartment adorned with oversize photographs of Audrey Hepburn, Judy Garland and Barbra Streisand. But millions share his splashy, over-the-top digital life: Since 2016, Rainbow, a Broadway hopeful who fled from cattle-call auditions, has found his own spotlight through the Internet, emerging as a YouTube sensation who dispenses musical-comedy salve for a divided nation.

Hundreds of thousands watch the short videos he produces every 10 days or so, featuring show tunes and pop songs he has refashioned with biting new lyrics. These DIY productions are funny and oh-so-topical and include clever video manipulation of news footage to create sassy mock interviews with prominent political players — mostly of the Trumpian variety — topped off with costumes ordered online.

It’s no secret that in 21st-century America, power over public opinion doesn’t reside exclusively with editorialists or news anchors. We are now Entertainment Nation, and society’s jesters — Stephen Colbert, Samantha Bee, John Oliver, Trevor Noah, Bill Maher, etc. — have become as influential as the Walter Cronkites and David Brinkleys of yore.

Rainbow, with his snappy riffs on the politics of the day, is a prominent part of this new and influential group, but he offers something distinct: a very old tradition of musical satire updated for the YouTube age. Think of him as a modern-day Gilbert and Sullivan, or the millennial version of the piano-playing Mark Russell or Tom Lehrer — the key difference being that his get-it-out-fast production marathons and savvy use of social media bring his commentary to the public quickly, directly and with no filter. Competitors like the Capitol Steps strive to put the mock in democracy as fast as possible, but with multiple writers and cast members, they can’t equal Rainbow’s speed. In a world on hyperdrive, he delivers near-instant gratification: Within minutes of Trump lawyer Michael Cohen’s appearance before members of Congress, for instance, Rainbow was taking song requests from fans on Twitter. Three days after Roger Stone was arrested in January, Rainbow posted “The Donald Trump Cell Block Tango,” a video parody of a number from the musical “Chicago.”

“He speaks out about how upside-down and crazy things are,” says singer-actress Lorna Luft, another fan who contacted him on Twitter and is now a friend. “Did the president just do a singsong in the Rose Garden like Jackie Mason? Seemingly seconds later, he’s been Randy Rainbowed.”

Rainbow, a Broadway hopeful who fled from cattle-call auditions, has created his own stage and spotlight.

On a chilly February afternoon, Rainbow is lunching at the legendary Sardi’s in Manhattan’s theater district, and the fans just keep coming by. “Watching you is a coping mechanism,” enthuses Anthony Meloni, of Rye, N.Y., stopping at the performer’s table. “You’re hysterical. Keep it up.”

Meeting with Rainbow is Jesse Kissel, the musical director and pianist for the show Rainbow is bringing to theaters nationwide. They’re plotting out the tour, which often goes into red or purple America — Des Moines, Kansas City, Cincinnati — where the large auditoriums are nevertheless filled and walkouts, theater owners tell me, are rare. Rainbow has parodied Bill and Hillary Clinton and shot barbs at other liberals, but he finds that the current administration showers him with comic opportunities. “The world’s attention is on Trump, and I’m part of that. Maybe when this is all over, Kellyanne [Conway] and I can have a drink together,” he quips.

Rainbow and Kissel need to figure out how a four-piece band can coexist onstage with an entertainer who appears in everything from a banana costume to a Mrs. Potts teapot and throws paper towels at the audience while wrapped in an orange boa. The two are still amazed that Live Nation, the entertainment colossus that produces 30,000 events in 40 countries each year, is sending a YouTube star on the road — that the same company that presents Jay-Z, Ariana Grande and Madonna reached into a bedroom in Queens and gave Rainbow the stages he longed to play.

Randy Rainbow brings his political commentary to the public quickly, directly and with no filter.

How did Live Nation hear about him? Credit one Bonnie Levitt of Scottsdale, Ariz. “My neurotic Jewish mother was pushing him on me,” laughs Andy Levitt, vice president of Live Nation’s comedy touring department. She sent him a video and, like a good son, Levitt watched. Although social media was Rainbow’s entry, Levitt understood that the singer-comedian is at heart a stage performer, so he gave him a contract. “He’s very likable and his fans are diverse,” says Levitt. “Kids are at the shows, theater geeks are at the shows. He is a hero to the LBGTQ community” — Rainbow is gay — “and, of course, my mom.”

A sampling of Rainbow’s hot takes includes “Desperate Cheeto” (a take on Luis Fonsi’s “Despacito”), “Border Lies” (Madonna’s “Borderline”), “How Do You Solve a Problem Like Korea?” (“Maria” from “The Sound of Music”) and “GOP Dropout” (“Beauty School Dropout” from “Grease”). Actor-comedian Steve Martin told Rainbow that “A Very Stable Genius” — a takedown of you-know-who sung to Gilbert and Sullivan’s “I Am the Very Model of a Modern Major-General” — is a favorite ditty in the Martin household:

He is the very model of a very stable genius

Of all the U.S. presidents he is the Mussoliniest

He learned a lot of things according to his Wikipedia

And demonstrates his ample intellect on social media.

When people are in need he is the best at making fun of them

He knows 11 words although he can’t spell even one of them.

Rainbow has become so popular that he has acquired a top Los Angeles agent, who is exploring television and film opportunities for him. He’s writing a book. The Manhattan accounting firm where he once worked as a receptionist now handles his money. His trademark pink glasses are but one item in his Randy Rainbow line of merch, which includes socks, Christmas ornaments, T-shirts, “covfefe!” mugs, tote bags and magnets for your car. In February, he appeared in the musical “Call Me Madam” off-Broadway; in a nod to his newfound celebrity, he was asked to wear his pink glasses while playing a lederhosen-wearing functionary in the imaginary duchy of Lichtenburg.

He has also caught the eye and ear of musical theater giants who applaud his clever concoctions. Broadway composers including Andrew Lloyd Webber and Stephen Schwartz have communicated their fandom directly. Stephen Sondheim, arguably the god of Broadway musical theater, spends a half-hour on the phone telling me that Rainbow’s lyrics are “brilliant” and “as good as anyone writing today.”

Mark Russell, who at 86 still writes song parodies that he posts online, is equally impressed by Rainbow’s ear for exactly the right musical match. “Something happens when the original title of the song just fits,” Russell says. “When I heard his ‘Kavanaugh’ set to ‘Camelot,’ I just about jumped out of my chair. Exactly right. … Why didn’t I think of that?”

“He’s like Brecht meets Jerry Herman,” offers Broadway director Michael Mayer, comparing Rainbow to the 20th-century German playwright and the composer-lyricist of “Hello, Dolly!” “Always dead-on. Always dead funny.”

Rainbow’s passion for performance arose early in a family in love with show business. “Mom would go to bed at night and pray that God would make her Bernadette Peters,” he says with a laugh. “I had a quick family. Very witty. I learned my rhythm from that.”

He was born in the Long Island town of Huntington, where his father, Gerry Rainbow, was a bandleader for the Huntington Town House, a now-demolished wedding and bar mitzvah hall. His mother remembers that Randy spoke full sentences at 18 months and was drawn to music as a toddler, especially the Broadway cast albums usually playing in the home. “I knew he was gay by the time he was 3,” says Gwen Rainbow, 68, a medical transcriptionist. “He was constantly putting on shows and making the girls be the prince. He was always Snow White.” After seeing “The Nutcracker” at age 6, Rainbow took ballet lessons for four years. “I had a boy but was also washing out tights and ballet shoes,” says Gwen. “He was two mints in one.”

His father eventually soured on New York and moved the family to Plantation, Fla., where he booked talent for the condo circuit, sang and played drums for hire. Randy was 10 at the time. His closest friend became his caustically funny maternal grandmother, Irene Frankel, whose late husband had been a bandleader. “They were a unit,” Rainbow’s mother says of her son and her mother. “I’d hear hysterical laughing from the two of them. She was the Bea Arthur type. She had opinions.”

When he wasn’t cutting up with his grandmother, Rainbow was captivated by puzzles, mazes and creating cartoons on his computer. He also spent hours making camcorder movies with his dolls. He spent so much time in his bedroom that one of his mother’s friends referred to him as Dracula. “She’d come visit and say, ‘Where’s Drac?’ ” recalls Gwen.

School, on the other hand, was difficult. Having a catchy stage name wasn’t exactly an advantage. “I joked my parents hated me by making me sound like a Care Bear,” he recalls. “It didn’t help on the playground.” Rainbow found his home in the drama department, winning leads in student productions, from Charlie Brown to Peter Pan to Sky Masterson in “Guys and Dolls.” “I was more butch then,” he quips. By senior year, he was barely taking classes, skipping several final exams and hanging out in the drama room, courtesy of a sympathetic teacher. He tried Broward Community College, then lived on the University of Central Florida campus with friends before landing a gig singing on the Regal Empress cruise ship out of Tampa.

Rainbow made the leap to Manhattan when a friend offered him a place to crash for three weeks. He set off on the tried-and-true path of generations of Broadway wannabes, auditioning for his dream while working menial jobs in order to pay the rent. A friend working at the Midtown Hooters got him a hosting job. “I wore a polo, khakis and a clipboard,” he remembers. “I can still see the disappointment when the men walked in and saw me.”

His best friend and current tour director, John Retsios, later got Rainbow the accounting-firm receptionist job that paid his rent and electric bills. The job made him desperate for a creative outlet, and he started writing. At night, he and Retsios hosted at Cafeteria, a gay restaurant in Chelsea.

He did a Web series for Broadway World, a theater website, including red carpet interviews for the Tony Awards and a late-night talk show, “Five Minute Call,” on theater topics. Then in 2011, he started editing himself into videos mocking celebrities — such as Mel Gibson (“Randy Rainbow Is Dating Mel Gibson”) — who screamed at women and underlings. “When the big guy picks on the little guy, that activates me,” he says. He also lampooned former congressman Anthony Weiner’s sexting misadventures (“Randy Rainbow Is Dating Carlos Danger”).

His satire is about “connecting with people who can’t accept the craziness and cruelty they’re seeing.”

His early videos were just gaining traction when his grandmother died in 2011. She missed her beloved grandson’s rise to fame by “just a little bit,” her daughter says. “It was the biggest heartbreak of my life. He was devastated.” Recalls Rainbow: “On her deathbed, she asked my mother, ‘How am I going to know when Randy gets famous?’ Not if I get famous, but when. She was such a believer in me.”

Her death had a profound impact on both Rainbow and his mother. He realized that his grandmother’s confidence in him meant that he had to take his talent seriously. For Gwen, the death pushed her to end her unhappy marriage. “When she died, I looked into the casket and thought, I’m next,” she remembers. “Six months later, I was divorced. She got me out of a 32-year nightmare.”

“My father was Donald Trump in many ways,” explains Rainbow. “His narcissism. I grew up with that generation of guys from New York, a generation of New York phony snake-oil-salesmen kind of energy. Before he died, my father said of Trump, ‘I can’t watch him, because he reminds me of me.’ My father had all that phony B.S.” Gerry Rainbow was a grudging, if jealous, admirer of his son’s talents and ultimately accepted his being gay. He died in 2017.

A large part of Rainbow’s shtick is inserting himself, pink glasses perched on his nose, into interviews with, say, the president, or Ivanka Trump, or Conway. He innocently questions their strange behavior — Trump mocking a disabled person or Conway believing that microwave ovens are cameras. He flashes his choirboy smile and weaves their words and actions into songs like “If You Ever Got Impeached” (“If I Only Had a Brain” from “The Wizard of Oz”) and “Microwaves (Are Watching You)” (Hall & Oates’ “Private Eyes”).

In a spoof interview with Vice President Pence about the border wall, Rainbow asks, “What are we calling it today? Two folding chairs and a bike lock?” Or, responding to Trump describing ousted FBI director James Comey as a showboat: “Those are pretty harsh words coming from the Titanic.”

Unlike late-night comedy hosts, Rainbow has no executives, sponsors or censors to please. Though he occasionally bleeps off-color words for comic effect, they are sprinkled openly throughout his routines. (A mild example from his parody of “Matchmaker” from “Fiddler on the Roof”: “Fact-checker, fact-checker, is this legit? Siri, ya there? Google this s—.”) “It’s a great thing about this Internet thing we’ve got going,” he says, smiling demurely. “I have the luxury of not going through filters or network execs to do my art.”

As someone with self-diagnosed attention-deficit disorder, he says he reads no newspapers or magazines (he doesn’t read music, either), getting his information chiefly from CNN, which plays constantly on large-screen TVs in his bedroom and living room. “I’ve got a good ear and a good eye,” he says. “I take notes throughout the day. I approach every video like I’m doing a book report.”

Here’s the regimen he follows about three times a month, ever since his musical satire of a 2016 presidential debate — built around the line “Super Callous Fragile Egocentric Braggadocious” — launched him into the viral stratosphere: After identifying a target, he spends about four hours writing new lyrics to a pop or Broadway standard, based on his obsessive knowledge of musical theater. Filming himself singing and conducting interviews takes another three hours. He pulls all-nighters for 10-hour edits with Adobe After Effects and Final Cut Pro, both of which he taught himself to use by watching YouTube tutorials.

The next morning, he uploads his videos to YouTube, to the delight of his 260,000 YouTube subscribers, 917,000 Facebook followers and 111,000 Instagram followers. “You are the only thing keeping me sane right now,” one fan shared on Instagram. “I owe you my liiiiife.” Rainbow understands those emotions. “I feel the responsibility of being a therapist to people who need it,” he says. “My main goal is to give people a little vacay from our troubles.”

A registered Democrat, Rainbow votes in elections, but he says that beyond his videos and performing for LGBTQ fundraisers, he is not politically active. He did write an op-ed for the New York Times defending Disney’s 2017 “Beauty and the Beast” movie when it was criticized for inserting a gay moment for character LeFou, played by Josh Gad, a childhood friend from community theater days at the now-defunct Hollywood Playhouse in Florida. But, he says, “I’ve never had a passion for politics. Still don’t.”

That doesn’t mean politics can’t rile him. When he’s not joking about it, he’s quietly angry about the Muslim travel ban, migrant children in cages and infringements on voting access and gay rights. He believes the country is getting bullied on the playground, and he feels the need to speak, even if humor doesn’t alter events. His satire isn’t about changing the world, but about “connecting with people who can’t accept the craziness and cruelty they’re seeing.”

I catch up with his tour at the Michigan Theater in Ann Arbor, where more than 1,300 fans have arrived for the show. Standing in line are Lynne and Jeanne Corwin. The baby-boomer sisters drove four hours from Cincinnati to see the show with their brother, Dan, and sister-in-law, Tammy Renner, who live in Ann Arbor. The three women are wearing the iconic pink glasses. “All six children in our family and their spouses are fans,” says Jeanne. “It’s the only way we can survive. It’s our therapy.” (Their mother doesn’t share their liberal politics, and they don’t share Rainbow’s videos with her.)

Close by are retired government lawyers Laurie Stewart, 58, and her husband, Steve Spaeth, 55. They moved to Brownstown, Mich., from Silver Spring, Md., a year ago, when she retired from the Securities and Exchange Commission and he from the Federal Communications Commission. “He says things that need to be said,” Spaeth says, laughing.

The show begins with video shout-outs to Rainbow from famous fans: Alan Cumming, Andrew Lloyd Webber, Debra Messing, Harvey Fierstein, Lou Diamond Phillips, Audra McDonald, Ed Asner, Mark Hamill and Barry Manilow. Rainbow enters to great applause and launches into a fast-paced rendition of his greatest hits. Many of his jokes and asides are nods to gay culture. In “Putin and the Ritz,” with Trump portrayed as the familiar orange cracker, a lyric says the bromance couple “really love dic … tatorships!” Halfway through the show, he confides, “I’m super gay. I should have led with that.”

Later, he tells the crowd, “This administration is doing scary, unsettling things and causing irreparable harm to our nation, but it’s been great for my career.” Indeed, income from two years of touring allowed him to move a year ago from a Queens studio apartment into his two-bedroom. As his mother describes it, “He had a lot of financial help from us that probably went on too long. But now he’s my retirement plan.”

Afterward, Barbara Yakes, an osteopath from Bloomfield Hills, is in line with her son, Allen Jankowics, 29, for the $40 extra meet-and-greet. A Republican who was a last-minute vote for Trump, she carries a pair of Rainbow’s pink glasses. Her son, a Bernie Sanders voter, is a broadcast and cinema arts graduate who is enamored of the technical competence displayed in Rainbow’s videos. He’s wearing a limited-edition blue Randy Rainbow T-shirt with a pair of pink glasses emblazoned on the front. “You can’t buy these,” he explains. It was a reward for donating to Rainbow’s Patreon account, an arts membership plan.

Both mother and son attended the show the next night as well, again paying the extra $40 each to take another photograph with Rainbow. That show was in Grand Rapids, near the home of Education Secretary Betsy DeVos; the crowd, Yakes reports when I call her for an update, was even larger despite the more conservative area. “Actually, there were a lot more boos for the Betsy DeVos clip in Grand Rapids,” she tells me, surprised that the audience booed DeVos. “Maybe people resent living with those millionaires.”

For her part, she disregards Rainbow’s jabs and just focuses on the comedy. “You can’t take politics all that seriously,” she says. “You have to laugh.” Which is Rainbow’s point exactly. “Comedy,” he tells me with a smile, “is always a healing thing.”

Margaret Engel is a Washington journalist and playwright.

Credits: Story by Margaret Engel. Photos by Marvin Joseph. Designed by Michael Johnson. Photo Editing by Dudley M. Brooks.