But We Loved is a production of iHeart Podcasts and The Outspoken podcast Network.
I did a show once, I think it was in Pittsburgh or Philadelphia, and this guy came up to me after the show crying and he's like, my lover died of AIDS. I'm going to lose my home because I don't have I can't afford to stay there, and my life has been in and I was thinking about ending it in Da Da Da. You literally made me forget about that for a half hour, and I was like, Okay, I didn't cure anything, I didn't solve any problems, but I gave this person a relief for a half hour,
and maybe that's all it was. But I was like, that's my job.
As a gay kid, growing up religious and in the South, I thought being gay was the worst thing I could ever be. Now, as a journalist, I'm trying to unlearn that by seeking out our history, and what I've found are people and stories full of courage, perseverance, and love. In this episode, we'll meet Cherry Vine, a legendary drag queen who came up in the same drag generation as RuPaul.
We'll learn about how drag has often been a source of escapism for the queer community, and how Sherry Vine was at the center of that during some of the darkest moments in gay history. From my Heart podcast, I'm Jordan and Solve this and this is what we loved. So I actually only recently got into drag. I kind of became obsessed with this last season of Drag Race. I hadn't ever really cared about drag before then, but once I started watching, it was like I was looking
forward to it every single week. And obviously I'm not alone because there are Drag Race watch parties across the country and the Drag Race YouTube account has over a billion views. As to why drag is so appealing to so many of us queer people, there are probably a million reasons, I know. For me tuning in every week to see these queens act ridiculous and where outrageous costumes and make really stupid jokes, It's kind of an escape
and it probably has been for generations. One of the first people to call themselves quote a queen of drag is the former slave William Dory Swan. He would hold these fabulous underground balls called Grand Rags in Washington, DC and his guests would dress up. Given how completely unacceptable it was to be queer in society back then, these events probably would have been everything to guests, an affirming space to be themselves and an entertaining escape from the
painful reality of being queer. This long tradition of drag queens entertaining our sorrows away has continued throughout time. My next guest, Sherry Vine, is a drag legend now with her own variety show on OutTV and millions of views on YouTube. But in the nineties, when she was just starting out in New York City, she was entertaining gay people through an existential crisis. Aids for Sherry, she realized she could make people laugh from an early age. I'm
here with the legendary Sherry Vine. You're here in full drag. I'm gonna describe how you look right now. So I'm there's squeeze your eyes almost tight, okay, gorgeous like almost like Jessica rabbit hair, and a sparkly gorgeous dress that's orange, fantastic cleavage.
All smoking mirrors. It look like a twenty two year old goddess. Just looked like my normal little hooker Barbie itself.
I love that. I love that. So we like to start the show off kind of asking everyone the same question, when did you know you were gay?
So I didn't officially come out until I was nineteen. Then looking back, I mean, I can remember being really young, like maybe five or six or seven, and I clearly remember seeing this guy on a motorcycle in my neighborhood, like he was dating the girl that lived a couple houses down. He was tattooed and rode a motorcycle. And I remember sitting in the front yard like playing with cars or whatever I was doing, and seeing this guy on a motorcycle and being like, oh my god, he's beautiful.
It's so funny because I feel like we all have some similar story, some variation of our motorcycle and basically, yeah, what was it like sort of coming of age as a gay person in the seventies. I know that you came out later.
But my school life was horrible. It was horrible. It was like the classic, you know, bully kind of abuse all and it was really horrifying, to be honest, and I I fought against it so hard. I'm not gay, I'm not gay. I'm okay that I think it just gave those people more. It was just fueling the fire. And I think if I had been in a different state of mind where it's like, yeah, I'm gay, I think it would have burst their bubble and that would
have probably made life a little easier for me. But that's not a way, right, So anyway, it was horrible. I'd have to invent different ways to get home, like every day.
Like I'd walk a different way, and they were bullying you for being gay.
Totally yeah, oh yeah. I would come to school in like skin tight jordash jeans tucked into cowboy boots and a perm. I had a perm and they're calling me bag and I'm like I am not and it's like, girl, you got a perm. So it wasn't even like I was trying to mask it, which I couldn't. There was no I mean I was a big sissy, so there
was no masking it anyway. And then at some point I kind of discovered I think I was a senior actually in high school where I was doing something in theater and on stage and making people laugh and I was like, oh, I'm making them laugh as opposed to you know, they're kind of classically Are they not laughing at me? They're laughing because I'm controlling why they're laughing. And that's when I was like, oh, Okay, this is
going to be a powerful tool. And also in that time didn't have gay and straight alliances like high schools have now, and didn't have Ellen, Will and Grace, all of these things that might have made it easier. Gay representation was not positive. Like I remember seeing the movie Cruising when I was like fifteen, and I remember leaving that movie like that's not I definitely am not that It's about a serial killer within the kind of s and m leather gay community of New York City, and
it was really graphic and dark and scary. Are you had drag queens that were always kind of like the sad, pathetic gay man who did drag for attention or whatever. It's just like there wasn't a lot of positive reinforcing gay a representation. Yeah, my parents loved Carol Burnett's show, they loved the Share Show. So we it would like, you know, a family thing to sit and watch these shows. And my mom will tell a story of like I was like three or four years old and Carol Burnett
would be on it. I would point to the TV and be like, that's what I want to do, Like what do you want to do when you grow up? That? And there was no plan be ever. I mean, it was very clear I was going to be a performer day one, and luckily they were super super supportive about that.
So tell me about how you got into drag.
Well, I consider what I do acting. There was no doubt that I was going to be an actor. And the drag part came about when I was in grad school getting my master's degree in Fine Arts at USC and I had a teacher, Anna Deavere Smith, who's a really amazing, amazing actress. She was the guest teacher, and we had this project where we had to spend time with like three different people, real people, and then write a monologue about the conversations. And I picked this businessman,
like very straight, kind of Wall Street type businessman. I picked this kind of nerdy art director who was actually an art director on The Peewee Herman Show. And I picked this drag queen and West Hollywood who was a little bit more what we would call old school like beaded gowns, glamour like glamour glamour. So in my mind, I wasn't doing drag as much as I was portraying
this character who happened to be a drag queen. And after the presentation, Anna told me a sound and she's like, there's something about when you were in drag that resonated, and she was brutally honest. She pulled me. She was like, you're gonna have a really, really hard time in Hollywood because you don't fit any time. You're not the leading man, you're not Tom Cruise, you're not really nerdy, you're not really offbeat like drug e looking, gangster whatever, like you
don't fit any of the characters. And she said, you're you need to create your own path, carve your own path, find someone to write for you, find a director, create a company, and create work for you, because otherwise you're gonna have a hard time. And I really listened to that, and I really took those words to heart, and that's exactly what I did. So how did you come up
with Sherry Vaughn Well? I started doing performing with my friend Robbie Daniels in La the two of us not in drag, but we would write parodies of songs and one day we wanted to this parody at the Price Is Right, and he wanted me to be the showcase model, and I was like, okay, I could do that, and oh it's drag great and went to my friend Carrie
French's house. She was a burlesque performer. She had like tons of gorgeous costumes and she dressed me, and my friend did my hair and someone else did my makeup and came on stage and I had this voice like, hey, it's me. I'm Shery, and that's literally how I was born. Then I was like, okay, I don't know if I want to be a drag queen full time.
Oh wow.
No, I was like I wanted to be a movie star, so this was still like character work for you for sure. And then I was in a play called Spira Keet that my friend Josh, who wound up being the director of theater tour, but this was in la he had his own theater company there. I was in that play as a man and this woman Robin sang the song black Coffee, this torch song, and I would sit in the wings every night just watching her, obsessed with that song.
I was like, I want to sing that song, but no one wants to see some skinny boy sing that song. So I said, wonder if share what it would happen if Sherry sang that song.
Because you had already created Sherry from like the price is right correct.
But it wasn't like a decision to kind of pursue it as a career. The first time I performed Black Coffee, I had this big blonde bubble wig, and I don't think that I looked glamorous. I was the character is supposed to be kind of like a slightly broken down, tattered show.
Girl, and how did the audience react?
What I walked away with from the audience was I haven't seen anything quite like that. And that's the first time that I really did something by myself as Sherry, and it just like took off. My befriend, Doug, who was living in New York. I told him about doing drag and He's like, I'm going to write a play and you're gonna come to New York and play the mother. I remember having this conversation with Doug where he was like, why are you fighting not wanting to be a drag queen? Like, no,
I'm an actor, I'm not a drag queen. I'm an actor. I'm not a drag queen. Why are you fighting that you doing something that there is an audience for and people want to see? And I was like, maybe you're right. And as soon as I let go of clinging onto what I thought was my dream, as soon as I let go of that and kind of embraced it, I was like, oh, this is one hundred percent the path that I am supposed to be on. Wow. And then yeah,
there was just no out that is amazing. Yeah, and hear we are thirty four years later, which is crazy, but I mean I just clearly remember it. And then that was it. I mean, it just kind of exploded.
What was that like moving to New York doing drag in the early nineties.
I think now a lot of people who start drag are like, oh, I want to be a TV star, I want to be rich and famous or whatever. Great, but that wasn't an option back then. No one was like I'm going to do drags, I can be rich and famous. This was not a possibility.
Wow.
Drag was still was not considered a legitimate art form. It was very fringe and you had to have a calling for it. Now it's very different. So anyway, it just felt like this calling. But like I said, it was a very different time. I remember I lived on Third Street and Avenue C.
That's pretty far out.
Oh and honey, let me tell you in nineteen ninety two, that was no man's land. Wow, Okay it was. You couldn't get a tax viar car in New York City. In New York City, it was real. And I would work at mostly like at the Pyramid in place in the eastward, and I had to walk, and I didn't have any money, so I had to.
Walk in your day drag wow.
And I just remember being like, Okay, this is my time, this is my time to go, Universe, please help me get to Pyramid tonight without being killed.
Yeah, tell me about that. What was it dangerous at that point to be walking around the drug.
Yes, yeah, I mean I'd been chased down the street with baseball guys with baseball bats. I've had bottles thrown at me. I mean, yes, it was dangerous.
It was all around that time.
Yeah, I did kind of become friendly with the guys that were dealing drugs on street corner. I wasn't buying drugs, but I was like flirting and like whatever, and they're like, don't worry, I got you, I got your mama, and they kind of had my bag. And then like a year later, RuPaul's came out with Supermodel, and that literally changed.
Like I can remember the moment where things changed, because one night I'm walking from my house to the Pyramid and people are like you freak, you're a man, and then all of a sudden they're like work Supermodel.
Wow.
Like then literally changed the way people started looking at drag queens and made it a little easier to like walk around.
RuPaul had released the song Supermodel in nineteen ninety two, and its impact was huge. It became a dance floor anthem, but also brought drag into America's mainstream consciousness. Meanwhile, Sherri was having the time of her life in downtown New York City being a full time drag queen. Tell me about what nightlife was at that point being a drag queen in New York.
He had to work every single night of the week, two or three shows whatever to pay rent and live because, like I said, it was not considered a legitimate art form, but it was really fun. It was really really fun New York City in the nineties, there were a million things to do every single night of the week. Wow, Monday through Sunday, there.
Was you're talking about going out, going out.
We would do shows. We'd get paid for that. There was Mark Berkeley ran this empire of big, big gay parties, like huge, big mega parties, and they would pay us just to show up and walk a hang out. We would show up, He'd give us a handful of drink tickets, and we were getting paid to hang out for a couple of hours. Then we'd leave and go. It was somewhere else so you could make a living. Not no one was getting rich, but you could pay rent and get by. There was Squeezebox, which I think started in
nineteen ninety three. Michael Schmidt started it and it was like a gay rock party and it was insane. This just before everyone had a camera on their phone. So, I mean, I can remember Drew Barrymore dancing topless on the bar and getting on Debbie Harry was always there, and John Waters and getting on stage with Green Day and Nina Hagen and Jone Jett. I mean, it was just endless, and it was every Friday night and they need have all these like straight guys who were just like, oh,
this is my chance to kind of experiment. And then there was Bardeaux and it was this live singing cabaret and it was really the only place in town where it was all drag, live singing, and it just really worked. And it was another thing that was just there was a line down the block every night to get in and it was fun. I mean it was the same time as AIDS, but I think the night life was so much fun. Also, in spite of.
AIDS, Sherry was enjoying the nineties New York nightlife scene as a drag queen. New York was affordable and incredibly fun. But at the same time AIDS was happening. For the gay community, this was an extremely dark time and many turned to drag shows as a way to escape the pain of their lives, the loss, the grief, the unfairness it all. Sheery was one of the many performers giving them that escape through her shows. But one signature part
of her drag was that she never got political. So it was a sounds like a really magical time to be working in part of it. Yeah, well, I you know that something about your drag sheery is that you never really get political. It seems that you sort of like to create this atmosphere where the audience can kind of escape almost for a little bit. Tell me about that.
I wasn't consciously trying to not be political. It just was like I was the comedy queen. My job is to make people laugh. I'm very political. I read the news every single morning. I read I think I'm pretty sharp on what's going on in the world. I have an opinion, I vote, but I don't integrate that into my act.
Historically, drag has always been an escape for queer people, the performer and the audience to escape kind of the pain of gay life or queer life. And I wonder if back in the day you were kind of conscious of that.
Well, yeah, I mean certainly. I did a show once, I think it was in Pittsburgh or Philadelphia, and this guy came up to me after the show crying and he's like, my lover died of AIDS. I'm going to lose my home because I don't have I can't afford to stay there, and my life has been in and I was thinking about ending it. In Da Da Da you literally made me forget about that for a half hour,
and I was like, Okay, I didn't cure anything. I didn't solve any problems, but I gave this person relief for a half hour, and maybe that's all it was. But I was like, that's my job.
What was it like being a drag queen in the nineties in New York City, which was sort of like one of the centers of the AIDS crisis.
It was a scary time. It was a sad time, it was a dark time, it was an angry time, and somehow, like I said, I think people were like, I'm gonna go out and have fun. This part of my life is horrible, so horrible and dark. I mean I was going to a memorial service every other week. So there was all that, and then there was just something about I'm going out tonight. I'm going to see this drag show and laugh and I'm gonna get laid
whatever it was, do you know what I mean? Like I'm not going to let it kill me until it kills me or whatever. I don't know.
We actually had someone from Act Up come on the show and she had described one of the most magical parts of Act Up. They would go out to these drag shows and it would sort of be an escape for them to immerse themselves in fun and play while they were outside of that, you know, fighting so hard
to survive. I wonder what was it like to kind of live in between those two worlds, Like, for example, you are an entertainer helping this community kind of have a few moments of living outside of their misery, but then you're also part of the community and you're being affected by the AIDS crisis too.
Well, it was intense. I mean I marched with Act Up in drag. I went to the March on DC in drag. Yeah. I mean, look, I can't think of any one day in certainly the first half of the nineties where I didn't know someone who was dying. Wow. Period, for sure, someone was always dying. So it was. And my best best friend, who had started the theater company with, who was my roommate, died of aides in ninety five.
I mean it was horrible. I remember being in complete denial, like the fact that he could actually really die, And I remember going to see him in the hospital and he was on a stretcher in the hallway because I didn't even have a room, like as sick as he was, we just were kind of like, he's gonna be fine. And then he came home and he kind of was
a bit better. And then, like I said, I think we were all just in denial, like he really wasn't better, obviously, but we were just coming he's home, he's gonna be fine. And we left at Christmas. I went to my parents' and he went to his parents and he never came back. When he died, it was like, wait, how how did that happen? Like it was almost like caught me by surprise that the reality was that this someone like although we had lost so many friends, it hadn't hit that
close to home. And I remember calling my mom to tell her and she just started crying and she was like, how is that possible? No one, no twenty three year old should go through losing half of their friends and the government not caring.
And then you performed at his memorial, right.
Yeah, I mean we one hundred percent. We're going to be in drag and we're going to have laughs, and we're going to celebrate his life and not you know, at pictures of him in a suit. What I remember the most is like even his mom and dad has brought and his sister were all there and no one was crying because we were just like celebrating this beautiful person.
Wow. And was it like that for you, like you would perform in drag at many different les. Wow.
It's weird now being this age because went through the AIDS crisis and then it was like, oh, there's this miracle drug and people are now living longer. Great. Then there's this section of time where I lost lots of friends to drugs. Now I'm losing friends like you know, cancer, heart attack, you know, more natural causes or whatever, because we're all going into our sixties.
Sherri had become the embodiment of living in two worlds at the same time. She was a drag performer, helping her community to escape from the world of AIDS with her comedy, but she was also inside of that community, losing her own loved ones as well. It sounds like being a drag performer is a lot. It's a lot of pressure. Was there ever a moment where you thought, maybe this is too much.
There was one brief moment in my forties where I was like, I'm gonna go back to school. I'm gonna get my PhD, like at Columbia in theater, and I want to teach acting on a college level, like not kids, I want to teach people who are like, this is what I want to do with my life. And then I sat down and I really meditated on that, and I was like, I'm not gonna be happy. I might be able to make myself happy, I will not be happy and I will not be fulfilled.
What about Drag makes you happy?
It's just so fulfilling. And I mean it's like acting. Like I said, I feel like I'm fulfilled as an actor and it's a character as long as people come to the show, and if they laugh and they like it, and or someone likes my videos or someone watches my variety show, then I feel like I'm fulfilled because I'm doing what I love to do, being true to myself of what I really passionately love and the benefit of someone agrees.
You love entertaining people. Yes, given everything that we've talked about, and the episode is kind of about, well, this element of escapism that Drag is for so much of the queer community that watches Drag. The AIDS crisis you mentioned drug addiction now kind of entering into this next stage with your friends. You know what losses and you know what people might be bringing into the venue when you perform for them. How does it feel for you when you see people smile when you're performing.
With everything going on in the world right now, the fact that anyone can smile is a testament. And if you're the person who's kind of responsible for making them smile, then isn't that political? M I mean, I see it as a form of activism.
It's radical.
Yeah, why not? But I went to I don't I really go out anymore because I'm sixty. I mean, I'm and I go to bed. I want to be in bed at ten. I rarely go out. And last night we did the Golden Girls and I was with Kelly Manton. She's like, let's just go and get a drink somewhere. I'm like, you know what, I'm dead tired, but let's just let's go to Hardware and see Shaquita, who I've known for thirty years and I love. She's like, let's go and walking there, I'm like, what am I doing?
Go home, go to bed. I'm like, no, no, And we get there and it's packed, like you can't move, and I'm like looking around, like, oh my god, I'm twice as old as everybody here. And I was like, so what. And she came out and people were losing their minds, screaming and yelling, and I was like, I love drag, not just performing in drag. I love watching Dragon and I always have and it's so exciting. And then I'm looking around this room and like, there's this
debate going on. Trump could win, there's the wars, and there's so much that's horrible, and the fact that this room is packed with people who are like screaming and cheering and laughing being entertained by this performer whose job it is to entertain. I was just like, this is why I love drag.
But We Loved is hosted by me Jordan Gonsolvis. New episodes drop every Wednesday. If you want to write in to tell your story, email us but We Loved at gmail dot com or send us a message on Instagram or TikTok at but We Loved. We are a production of The Outspoken Podcast Network and iHeart podcas. But We Loved was originally developed with Pushkin Industries. Our producers Areshena Ozaki, Michael June, Emily Meronoff, and Joey patt Our. Executive producers
are Me Maya Howard. Fact checking by Marisa Brown. Original music by Steve Boone. Special thanks to Jay Bronson and Roquel Willis. If you loved this episode, leave us a rating and follow us on Apple Podcasts and Spotify, and thank you for listening. I'll see you next week.