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Getting Randy for Christmas

Musical satirist Randy Rainbow gained a following with his politically oriented videos. Now this self-proclaimed ‘bad Jew’ is taking on Santa.

Peter Fox
December 24, 2019
Photo: Dirty Sugar LLC
Photo: Dirty Sugar LLC
Photo: Dirty Sugar LLC
Photo: Dirty Sugar LLC

Randy Rainbow calls himself a “bad Jew.” The musical satirist dropped out of Hebrew school as a kid, and is obsessed with Christmas. So obsessed, in fact, that his debut album, which debuted at No. 1 on the Billboard comedy charts and No. 1 on the iTunes holiday chart last month, is called Hey Gurl, It’s Christmas!The album puts a new spin on classics like “Santa Claus Is Coming to Town” but also contains original material, including a chilling romantic duet with Norm Lewis, displaying the comedian’s gift as a versatile and serious artist. Rainbow wrote lyrics with Broadway composer Marc Shaiman (Hairspray) for the album, and has comedic interludes and duets with Kathy Griffin, Alan Cumming, and Lorna Luft.

“I celebrate everything,” Rainbow told me (yes, that’s his real name). “We always had a menorah and a Christmas tree—not for any reason other than we always liked celebrating things.”

Dubbed a “queer hero of the resistance” by podcaster and columnist Dan Savage, Rainbow has become an internet sensation for his musical parody videos riffing on Donald Trump and his administration.

His uncanny ability to produce quickly edited mock-interviews and parody songs hours after a scandal breaks has made him one of the most alluring forces online. It’s earned him nearly 2 million avid followers across social media, which has manifested into a full-blown showbiz career. He’s selling out live concerts nationwide and earned his first Emmy nomination this year for outstanding short form variety series.

The 38-year-old entertainer is like an eccentric fusion of Weird Al Yankovic and Allan Sherman. On-screen his heightened persona radiates like a character straight out of a children’s program like Sesame Street but with a twisted humor punctuated with unabashed gay sass. His signature pink sequined cat-eye glasses that he wears in his videos have become so iconic that he now sells them on his site. The authenticity in showcasing his full unfiltered personality has added to his success, when a decade or two ago that could’ve been a near certain career barrier. Instead it’s helped enshrine his personal brand as being a singular voice that stands out from everyone else in comedy.

A slew of celebrities has championed his work, like Mark Hamill (aka Luke Skywalker), Debra Messing (Will & Grace), and legendary Broadway composer Stephen Sondheim—who has lauded Rainbow’s lyrics, telling The Washington Post that he is “as good as anyone writing today.” Even Hillary Clinton sent Rainbow a fan letter thanking him for his work—a note he keeps framed in his apartment.

To his die-hard fans, Rainbow is more than just a whimsical entertainer, but a true savior in an era of chaos and despair. The comment sections of his videos read like a gospel of spiritual-level praise. One fan writes: “You make this nightmare we’re living in tolerable” and another person says, “When my future kids ask about the Trump era fiasco, I’ll sit them down and have them watch all Randy’s videos.” Or simply: “Love your contribution to our sanity.”

Though Rainbow prides himself as being more of a show queen than a political wonk, he acknowledges that his sudden rise in fame is attributed to the unique niche he crafted from the current state of political turmoil. “The reason I created this shtick—this gimmick—is because it allows me to go wherever the headlines go,” he told me. “As long as there are headlines I can always Forrest Gump myself, as I call it, into whatever everyone is talking about. There will always be controversy.”

Rainbow attributes his love of theater to his family, whose musical roots run deep. His grandfather was a bandleader and his father made a career as a drummer and singer for hire.

He benefited from supportive parents who accepted their son’s differences from the start, allowing him to take ballet lessons at 6, record home movies with his dolls, and go to theater camp. “My whole family was very accepting,” he said. “Whatever makes you happy—that’s sort of a very Jewish theme, I think. Sometimes. Depending on what type of Jews.”

Rainbow’s Jewish upbringing also had a big impact on his sense of pride and humor—even though he dropped out of Hebrew school. “Culturally I’m very Jewish,” he said. “I like to incorporate Yiddish words. I just think it’s hysterically funny. There’s not one Yiddish word that is not perfectly funny.”

Take the phrase oy gevalt, for instance, which he sprinkled into his video “Omarosa!” (a parody of Oklahoma!) “There’s a musical aspect of it that’s funny,” he said.

When Rainbow was 10, his family moved from Long Island to Plantation, Florida, a suburb between Miami and Boca Raton where his grandmother would become his best friend and biggest champion. “It was really my grandmother who was the biggest influence because she’d talk back to the celebrities and politicians on TV,” he said in a 2017 New York Times interview. “She was a combination of Joan Rivers, Elaine Stritch, Betty White, and Bea Arthur rolled into one.”

His family was filled with equal parts love and tension. “My father was Donald Trump, and my mother was Hillary Clinton, and my grandmother was Nancy Pelosi,” he told me. “And I was—I wanna say, Mike Pence, ‘cause he’s the gayest one.”

Rainbow began his career singing on the Regal Empress cruise ship outside Tampa after dropping out of community college. With a friend’s help, he moved at 21 to New York, where he worked at a Midtown Hooters to support his Broadway dreams. (“I can still see the disappointment when the men walked in and saw me,” he recalled.) When he wasn’t landing gigs, he started writing his own material. He launched a blog and taught himself how to use Final Cut Pro and Adobe After Effects, which he learned from YouTube tutorials.

His friend and current tour director John Retsios eventually helped Rainbow land a job as a receptionist at a Broadway accounting firm. It was from this experience that he started making YouTube videos as a creative outlet. His first taste of viral fame came in 2010 when his parody video Randy Rainbow Is Dating Mel Gibson made its rounds online. This viral video led to a job at the theater site Broadway World where he would get paid to host a web series conducting red carpet interviews at the Tony Awards as well as host a backstage talk show series, Five Minute Call, where he’d interview actors behind the big shows. Through this job he started developing a niche profile as a talented comedian and Broadway aficionado.

It would take another six years, however, for his career to take off to where it is today.

In 2016 he catalyzed from obscurity when his parody of the Trump/Clinton debate, “Braggadicious,” became a viral hit, garnering over 20 million views in a matter of days. “When the shit hit the fan, it really took it to the next level,” Rainbow said. “One day I put the musical and the headlines together, and it worked for some reason.”

Since then, he’s been a dominant fixture of the internet. A sampling of his most popular videos include “How Do You Solve a Problem Like Korea?” (spoofing “Maria” from The Sound of Music), “Cheeto Christ Stupid Czar” (Jesus Christ Superstar), and “Rudy and the Beast” (you get the gist). All the more astounding is that he makes these videos out of his bedroom entirely by himself. His only companion is his Persian cat, Mushi, who he calls his “executive producer.” His process of making a video is a marathon. He starts with finding a news story that’s ripe with controversy before spending about four hours writing, then recording vocals. Then he films himself in front of a green screen for another four hours and stays up all night editing.

He repeats this process about every 10 days.

Behind the smiles and sunshine in his act, though, is a serious artist. “While I might be flashy and laughing and joking and singing show tunes, the foundation of it is anger,” he said. “That’s the seed of any real successful comedy.”

For the last three years his videos have exclusively focused on the Trump administration, but with the 2020 primaries approaching he says he’s excited to switch it up.

“I have lots of lists of song parodies ready to go for Democrats—no one’s off limits,” he said. “If it calls for it, I’m ready to dress up as Elizabeth Warren.”

Last month, Rainbow performed his largest show yet in front of a sold-out crowd of 2,800 at New York’s Beacon Theater. He chose trailblazing comedian Judy Gold to open for him. Both are gay Jewish comedians of different generations, but the level of acceptance three decades ago was very different from where it is today, which he has greatly benefited from. “She doesn’t get the credit that she deserves and really came out before Rosie and Ellen, who I love,” he said. “She was having a show business career as an out lesbian before that.”

His show began with a montage of fan-submitted videos expressing their gratitude for his work, which segued to many of his newly minted celebrity friends—including Barry Manilow and Harvey Fierstein—doing the same.

“We’re gonna laugh until we cry,” he told the audience. And who was in that audience? Gretchen Carlson, the former Fox News host who exposed Roger Ailes’ sexual harassment. And Sondheim himself—seated next to Rainbow’s mother.

Rainbow’s career has brought him enough success to move out from his walk-up apartment in Astoria, Queens, to a luxury apartment in Manhattan’s Upper West Side. He says producers are interested in bringing his brand of comedy to TV.

Rainbow has won the adoration of many of his childhood heroes, but the connection he is most humbled by are not the celebrities or entertainers, but the Parkland families who befriended him in the aftermath of their deadly high school shooting. “They’ve found a lot of comfort in my work,” he said with misty eyes. “I first heard from them ‘cause I did a video parody of ‘Kids’ from Bye Bye Birdie, and it was sort of an homage and celebration of the Parkland kids and they reached out saying they were fans of it.” Months later he did a show in Florida and they all came to see it. “They’ve found a lot of comfort and healing in my humor.”

Here lies the power of Rainbow’s influence, not just as an entertainer for laughs, but as a shaper of culture. His work has managed to transcend stereotypes and provide a sense of relief for people who need it the most.

“Comedy and humor are a coping mechanism,” he said. “Turn to art and turn to humor and turn to music, and I hope people realize how healing those things can be.”

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Peter Fox is a social commentary writer whose work has appeared in CNN Opinion, Newsweek, The Jerusalem Post, and other publications. Follow him on Twitter @thatpeterfox.