A few years ago, Randy Rainbow thought he’d reached the height of his fame, making comic music videos in his apartment about people in the news. Then, in 2016, he made a video lampooning the first presidential debate called “Braggadocious!” The video got millions of views overnight on Facebook — it currently stands at 31 million — and Rainbow found he had a lot of room to grow. Now he’s touring theaters with a musical live show that comes to the Wilbur Theatre Thursday. He’ll also be the guest of honor at the Elliot Norton Awards on May 21, a ceremony that honors the year’s best in Boston theater.
“I got a nice following,” says the 35-year-old of his earlier videos. “I was very content, actually. I thought I was extremely famous back then. I had no idea there was more ground to cover. But it certainly hit a new level in 2016.”
In the “Braggadocious!” video, Rainbow inserted himself as moderator into footage of a debate between Donald Trump and Hillary Clinton. Increasingly irritated by Trump, he launches into a parody of the song “Supercalifragilisticexpialidocious” from “Mary Poppins.” He’d had popular videos before, including a parody of “Cell Block Tango” from “Chicago” aimed at Kim Davis, the Kentucky court clerk who refused to issue marriage licenses to same-sex couples.
The debate video made Rainbow an overnight success. And like many other overnight successes, he had been working for years to get to that point. “That felt different,” he says. “I could tell something was going on. But every step of the way is kind of new and exciting. When the Kim Davis thing hit, I thought that was it. When I got my first thousand views on a video on YouTube, I thought that was a huge thing.”
One of the bigger perks of his success is that he often hears from the writers and composers whose work he parodies. “As a musical theater nerd, [that] has been the most thrilling part of this,” he says. “[Stephen] Sondheim is a fan. I can’t believe I hang out with him regularly. I heard from Andrew Lloyd Webber when I did a parody of ‘Jellicle Cats,’ that was ‘Alternative Facts.’ I mean, it’s crazy.”
He says he’s honored to be a guest at the Elliot Norton Awards, which are voted on annually but the Boston Theater Critics Association. “I didn’t really realize what company I was in until recently,” he says, then jokes: “They’ve had Chita Rivera and Al Pacino. So they’re finally getting a real celebrity.”
Rainbow was born on Long Island and raised in South Florida. “My family was really into musical theater. My mother used to put me to sleep with the cast albums of ‘Oklahoma’ and ‘The Music Man.’ ” He jokes that she was rooting for him to become a gay musical nerd. “She really had a plan for me,” he says. “And bless her, because it’s really working out now.”
When he moved to New York at 21, he had no career aspirations. He still loved musicals, especially musical comedy, but he didn’t move to the city with the dream of becoming a Broadway star. His first job was as a host at a local Hooters because his roommate had an “in” with the manager. “That was my start in New York, as a Hooters girl,” he says.
From there, he moved on to receptionist jobs at a company that produced theater and another at an accounting firm that did the books for Broadway shows. The jobs bored him to tears, but he was close to the theater again, and started writing a blog. That led him to a job with BroadwayWorld.com, trying to find creative ways to deliver the headlines, which is where he had his first success making videos. “I think it was like a Tony Awards special where I announced the nominees using a well-known Broadway song,” he says. “And that was popular, and I just stuck with it. Somehow the two merged and I ended up putting the musical stuff with the politics and that worked somehow.”
Rainbow has continued to make popular videos, most recently goofing on Rudy Giuliani’s defense of Trump with a “Beauty and the Beast” parody. He might still make the videos in his apartment, but he notes the apartment is a bit bigger now, and he’ll eventually get successful enough to find a separate workspace. He continually hears from new fans who thank him for relieving the stress of an administration they find oppressive.
The videos also got him back to his original dream of being a live performer. On this tour, he’ll interact with some of his more popular videos and stretch a bit. “This first incarnation of the live show is really all about the music,” he says. “I say it’s kind of a musical celebration of the demise of our country. But it’s all my greatest hits. So there’s a big screen behind me and interactive videos that segue into the musical numbers, and I do them all live. And there’s some stand-up comedy woven in, and a Q&A. And it’s a whole hodgepodge.”
Performing for a live audience is a dramatic shift from making the videos. Rainbow is a one-man operation, doing everything from video editing and production to his own makeup (which he notes is all from Duane Reade). The only thing he doesn’t do himself is play the instrumental tracks. Everything else is created in his apartment in Queens, each video taking roughly 48 hours to produce.
It’s quite a different experience to stand in front of fans and get immediate feedback. “Anyone who does Internet content of any kind will tell you it’s a very isolating experience to actually make it,” he says. “So to even be able to tour the country and be in cities I’ve never even been to before and be greeted by theaters full of hundreds and sometimes thousands of people is amazing.”
Rainbow’s fanbase can be a dedicated bunch. He sometimes sees them wearing his signature pink cat-eye glasses. But what has surprised him most is how earnest they can be. “When I make the videos, my intention is just to be silly and make people laugh and be amusing,” he says.
‘I heard from Andrew Lloyd Webber when I did a parody of “Jellicle Cats.” . . . I mean, it’s crazy.’
“But I hear ‘thank you’ about 700 times a day. I never expected to get so much gratitude, but I think it’s just a testament to how important humor and musicals, musical comedy, can be in times of peril. It certainly always has been for me.”
At the Wilbur Theater, May 17 at 7:30 p.m. Tickets $38, 617-248-9700, www.thewilbur.com
At the Elliot Norton Awards, Huntington Avenue Theatre, May 21 at 7 p.m.. Tickets $35, www.bostontheatresceneNick A. Zaino III can be reached at firstname.lastname@example.org.