RuPaul confides in Bowen Yang about his career ‘scars’ and verging on Emmy history

RuPaul and Bowen Yang spoke together for almost an hour in a wide-ranging conversation.
(World of Wonder; Chris Pizzello/AP)

RuPaul Charles and Bowen Yang are unquestionably LGBTQ+ trailblazers. Over three decades, the towering Supermodel of the World has brought the art of drag into the mainstream with an individual career that has defied the odds and spearheaded a global franchise that is the Emmy-winning “RuPaul’s Drag Race.” The multitalented Yang is not only the first featured player (as opposed to full cast member) from “Saturday Night Live” to earn a supporting actor in a comedy nomination, but also the first Chinese American. They are on the verge of landing in the record books this Emmy season and they also have, for lack of a better word, history.

Here, The Envelope listened in as the two pioneers talked to each other on a video call — RuPaul from Los Angeles and Yang from New York — about Emmy history, mentorship and the power of “Dynasty.”

Their conversation has been edited for length and clarity.

RuPaul Charles: I haven’t seen you since we did “SNL” together. But I have a lot of great memories from that happening.


Bowen Yang: Do you?

RuPaul: But the No. 1 memory is us in the sketch that got cut. Where we’re the bitchy coal miners.

Yang: Am I one of the only people in television history who’s thrown a drink in RuPaul’s face? I can’t believe I got to do that.

RuPaul: Oh god, it was so funny.

Yang: I’m bummed that it got cut. I don’t know how you feel about this, when things like this happen, when you’re so racked with disappointment. I remember that was one of the most disappointing shows for me because I was so emotionally invested, because it was you. I was like, “Who else is going to come along who I’m so inspired by? Who I’ve looked up to for so long? Who’s done so much?”

RuPaul: But that sketch, it does live on YouTube. And it is ha-larious. It is so twisted. So twisted.

Yang: I remember you and [“Drag Race” executive producer] Tom Campbell sat in an office with me and James Anderson, the cowriter on that sketch. We were just quoting “Dynasty” for hours, and I was like, “This is heaven.”

Bowen Yang as The Iceberg That Sank the Titanic and Weekend Update anchor Colin Jost.(Photo by: Will Heath/NBC)
Bowen Yang as The Iceberg That Sank the Titanic and Weekend Update anchor Colin Jost
(NBC/Will Heath/NBC)

RuPaul: How did you get introduced to “Dynasty”?

Yang: I was introduced very late to “Dynasty” because my parents didn’t know what TV was. I was probably introduced when I started doing comedy in New York with my friend Oscar Montoya and he was like, “We should reenact the scene from ‘Dynasty.’” It was when Alexis [Joan Collins] and Dominique Deveraux [Diahann Carroll] were fighting. Not the scene that we had based the coal miner sketch on, but when they finally come to blows in someone’s bedroom.

RuPaul: On [“SNL”], you went from writers room to featured player. What was the chronological order?

Yang: I auditioned a handful of times to be in the cast. I was like, “It’s never going to happen but let’s just have fun with it.” This was right around the time when I listened to your Marc Maron [podcast] interview. It was just so illuminating and it was like, “Just don’t take life too seriously.” I really kind of sustained that idea throughout my audition process. Then by my final meeting with Lorne [Michaels] ... he hired me as a writer. He had the intention of putting me on camera but he kept saying, “You’re going to be scrutinized in a way that other people might not be, and so I want to make sure that you’re set up for success as soon as you’re thrown out there in front of the camera. Because you are going to be evaluated differently, based on these things that are not in your control but are completely dictated by what society thinks.”

Speaking of mentorship, do you feel like you are now starting to look back on “Drag Race,” as this figurehead, as someone who is able to launch careers? In ways you’re changing the material reality of these people who come on the show. Is there a throughline into what you hope is upheld by these girls leaving the show and performing outside of it?

RuPaul in full drag  Credit: VH1
RuPaul in a moment from “Drag Race.”

RuPaul: I hope that what we go through here, in the process of creating the show, and making and filming the show, they can carry that experience with them. Because our challenges are based on things that I’ve done in my career and crafted to challenge a person to be willing to die in their old self and be reborn into their higher self.

Yang: That happens all the time.

RuPaul: All the time. And that is life. You have to be willing to let go of old ideas and open yourself up and channel the source. So that’s what I hope the girls continue to do. And it’s not easy to do.

Yang: So, this is my first Emmys campaign event and I’m thrilled that it’s with you. What advice do you have? I mean, you’ve collected plenty of hardware here. What’s your advice on campaigning, in general?

RuPaul: Honestly, it’s a cliché, but being nominated, the period of being a nominee, it’s a long period and it’s so exciting because it’s sort of a very exclusive club. And you’re nominated and I think it’s the first time it’s ever happened where a featured player on “SNL” was nominated.

Yang: For a featured player, but it’s a matter of timing. Back in the day when you had Eddie Murphy pop off, I mean, the Emmys, the categories were different back then. I’m just the beneficiary of really fortunate timing in all of this. It’s great. But this is what I always take away from you, “Don’t take life too effing seriously.” But then isn’t campaigning for Emmys, the pageantry of this, isn’t that taking life seriously?

RuPaul: Well, I’ll tell you what it is. It’s taking all of the people who work with you to help create this incredible machine of comedy and beautiful pictures, it takes their work seriously. Because you represent all of the people at “SNL,” and all of the comedy clubs you’ve visited, and all of the people who have supported you throughout your career. That’s the serious part. The fact that you’re being recognized is recognizing all of those people. So yes, it’s important to not take life too effing seriously, but there are things that one should take seriously. And that is the kindness and love and support that all the people who have championed you throughout your life — this is actually for them.

Yang: I want to ask you about something else that’s historical. You are maybe on track to be the most awarded person of color in Emmy history. Does that mean something to you? Because I think even if it doesn’t, it still is tied very neatly into the fact that you, as RuPaul, have put more Black and brown queer people, trans people, what have you, on TV than anyone else, ever. Ever!

RuPaul: It does mean something to me. I have all the scars to show you from a career in show business. Actually, I climbed up on stage, the first time for money, in 1982 and I’ve been doing it ever since. It’s been a long, hard road, but I have enjoyed every minute of it. I dig being creative and music and colors and shapes and the laughter from people and discovering something really beautiful in these contestants, every season. So, the history sort of means other people are keeping track of things.

Yang: Yeah, yeah.

RuPaul: I’m keeping track in my heart and in my experience and in my own story. What it means to other people, that I’ve been the first to do this, or in history, or all that stuff, that’s great. That’s fine. But for me, it enriches my experience. What other people think of me is none of my business. I didn’t get into this thing to try to get other people to like me or love me or validate me. I did it because I have to do it. I did it because I love to create. I’d be doing this had I not become famous. I’d be doing this in some form or fashion.

Yang: I got really drained recently, when I was going to Pride events in the city. Things were reopening and COVID cases weren’t too bad here. So, I was kind of out and about. I love meeting people, but I did find myself feeling drained by the end of each experience, being like, “Oh, people are really coming at me with their emotions.” And that’s beautiful, but I feel like there was procurement that was taken out of that. What I realized was, in order to recalibrate, the only way to give back to yourself is to create, to make something for you. And it’s not a self-serving thing. It’s not selfish. It’s something that is necessary, in order to keep moving through it.

RuPaul: That’s right. That’s that touchstone to your heart and the thing that gets you out of the house and that drives you forward. Because it cannot be for the validation of people outside of you. We’ve tried that trick. It never works. And I can understand. Every time someone says, “Oh, you’re the first this. Oh, you’re the first time ...” People right now are obsessed with, “You’re the first in history to do this.” It’s like, “Wait, what? Oh, great. That’s not really why I’m doing it, but I’ll take it.”