I, Sky Gilbert, the happy outcast

Theatre's enfant terrible on his new novel I, Gloria Grahame, cruising at the age of 60+, the naughtiness of art, and the practicalities of maintaining an open relationship

In a Gilbertesque twist on the usual order of things, I first saw Sky naked, then met him in person. Before his relationship with Buddies in Bad Time Theatre soured, he was a regular on its stages and the very avant-garde production of Lulu back in 2018 put the entire cast au naturel in the final act. Author of many novels, one of Canada’s most produced playwrights, thrice Dora winner, University of Guelph Prof Dr. Schuyler Gilbert was living a comparatively quiet life of an elderly gay statesman when he found himself at the centre of a purity spiral scandal, cancelled from the theatre that he founded with a group of friends before the current crop of activists were a twinkle in their parents eyes. The online shaming raged for days, and the theatre itself produced a live-stream of the round table on hurt feelings. (Look for Sky’s Quillette pieces on this surreal episode.) Arts media didn’t know what to make of it and hedged or sat on their hands. It’s when I emailed him, never having met him before, to essentially say WTF?!

We started hanging out and got together with two other artists, then each of them dipped into their own networks and it looked like there was some critical mass for a free speech coalition for the people in the arts and book publishing. Then the covid pandemic hit and atomised us all back into our private lives. But Sky and I kept hanging out. He’d come over from Hamilton to his usual guest house on Church for the weekend, and when every door in town was closed and everybody saw in other people only vectors of disease, there we were, frozen-ass, walking over grimy black ice of the downtown East End, talking loudly through our scarves, alternating disbelief, anger, sorrow, and sometimes even worked it up to mirth, over the state of things.

Through all that we’d share bits and bobs about our writing, and I did hear occasionally about the novel he was working on. It was eventually acquired by Russell Smith at Dundurn and came out in autumn last year. I adored it from page one. It’s wickedly funny, in both of its voices, the hapless elderly gay narrator and his literary drag persona, based on a Hollywood tough broad in the mold of Mae West. The two share a story (and shame) of an unseemly desire – for a much much younger person. Over the voices of Denton and Gloria, comes the play Denton wants to produce about Venus and the much younger Adonis. Phaedra and Hippolytus make an appearance. Shakespeare, this being a novel by Sky Gilbert, never leaves. If I made it all sound like a grad school essay, it’s anything but. It’s naughty, not a little trashy, and did I mention funny. And full of compassion for human sins and failures.

I.

Sky Sky Sky. The scene in the arts council, where Denton needs to explain the political relevance of his proposal to the grant officers. You know that with that in, nobody was gonna dare touch this book, put it on award shortlists, review it in the mainstream media.

I’ve accepted my outsider status in the Canadian literary scene long time ago. I was lucky if I got reviewed in the mainstream. And now I think until I die [giggles] I may never again be reviewed in large papers. I’ll have to wait till I’m dead.

The gays are out of the mainstream again.

Yes, they had melded into the trans politics and the antiracist politics and that’s what they’re about. I understand that. I’ve already abjured that. The only thing is now, can I find an editor or publisher now and again who is going to publish my work. And I suppose… when I have that feeling that I get when I write something that I worry isn’t going to get published, or that it’s too dangerous – that’s a good thing.

The three interviews at the arts council, it’s like having to solve three riddles in a fairytale. One was, how dare you create a male character who’s pretending he’s female – without it all being about trans people. The second is why is a man playing a female role when there are not enough roles for women in theatre (which is true). The final one was why would we fund another one of the “white male” projects again. It’s so cringe, that whole process, but he improvizes the answer for the final one and it’s suddenly insanely funny.

The “Uncle Tom’s Cabin” was a total accident, because I remember thinking he had to pull something out of his ass at that point – and I looked it up, and it was a code word for an actual entry point on the Underground Railroad. So I thought, this is too felicitous. I have to use it.

My editor helped a lot with the second dialogue that the woman delivers. “You’re taking away our voice” etc. But I do have some experience with that. I did a play years ago that’s never been published, A Few Brittle Leaves, it was extremely successful with audiences, with Gavin Crawford and Ed Roy in lead roles. It was inspired by the novels of Barbara Pym. I have this fascination with English female novelists of the 1930s-40s-50s. So the production was well received but when I went to get it published, I was told We just feel this is taking away parts from women. It was written for Gavin and Ed to play women. Gavin really played as a woman; if you didn’t know it was Gavin, you wouldn’t be able to guess. Ed kind of did it the drag style; he played the crazy character, he was extremely funny and clownish, whereas Gavin was subdued and very sympathetic. The play was supposed to be about spinsters, and how gay men have a lot of spinster mentality. That’s what I wanted to write about. How we have this notion that we have to get with a man, that we would be otherwise alone… there are similarities. It’s like this book, really. Nowhere does it say here that this is Gloria Grahame talking. It’s always Denton, making up Gloria Grahame.

Ed Roy and Gavin Crawford in A Few Brittle Leaves. Photo by Tanja-Tiziana / Buddies in Bad Times Theatre

And then there’s Venus, speaking through both of them. But what’s also funny about the arts council scenes is… the guy who’s policing race is only a fraction the ethnic minority for which he is a self-proclaimed spokesperson.

One of the things that came up late in the edit was the painting of Kent Monkman in the arts council office. I’ve only met Kent a couple of times and he was charming to me, but I know my friend Gavin is friends with him and I worked with his ex partner… I got a recommendation for the book from Tomson Highway, and I don’t think Kent and Tomson have different views on sexuality; Kent Monkman identifies as a drag queen; he may also identify as two-spirited but he’s also a drag queen. If you look at the way he presents that character [Miss Chief Eagle Testickle], it’s also extremely sexual. Drag is sexual which is also why I don’t think it’s a great idea to teach it in kindergarten.

Now of course Kent too has gotten in trouble. Which I find fascinating. He painted laughing Aboriginal women in a painting in which a dildo was being shoved up Trudeau Jr’s ass. I don’t understand why all this sudden pursed lips-ness over that laughter. But it’s the essentialist thing again; he’s a man, so what can he know about women.

II.

I wanted to ask you about aging and dating. There’s a lot on aging in the novel. I think you’re open to talking about the fact that you have an open relationship?

Yes, I think it’s important that I talk about having an open relationship because open relationships are an important aspect of what gay men have to offer – culturally. And lesbians too; alternative relationships, bunch of lesbians living in the same house, ex partners who remain friends, there are all kinds of ménages. Lesbians have their own versions of alternative relationships.

Do you date online? It’s a young person’s game, I think.

I don’t date online. When covid hit I had to do a little bit of it and I hated it. I didn’t understand it; I would never do it. I’m glad – well, knock on wood -- I hope I don’t ever have to go on Grindr and such. It's not for me. I'm not looking to date, I'm a 'bathhouse/ backrooom' type guy.

So do you just go to bars, like Denton?

Yes. But I have much more fun than Denton does, I’m much more in control of my sexuality than Denton is. I don’t obsess about students, and I have a partner. Generally speaking, there’s much ado about nothing when they’re going on about how hard it is to be an old gay man. Denton is an example of someone who falls through the cracks, but the bear culture makes a place for older gay men. It’s the hairiness, fatness… it’s furry-fat men as opposed to boys. Men of authority, older, all that stuff… that’s bear sexy. It’s a little bit sexist, bear culture, even. And I have some of that, I have a little bit of bear in me. But Denton is a girly, older man.

He’s feminine.

And I’m effeminate but I’m also bear-looking so as long as I don’t open my mouth—and if men aren’t too sensitive to me being effeminate, then I can get by, but if you *look* effeminate, yes it’s harder for older men. There’s a bit of a problem. The other thing that the effeminate men have going for them and I don’t have going for me is that if they assume a certain role, in gay culture everybody knows how to deal with them. It’s like, gay men will fuck them, they can dominate them.

Does effeminate always = bottom?

Not always, but one of the problems I have getting laid is that I’m kind of a secret bottom. I’m not that much of a top! People will take one look at me and they’ll want me to dominate them. That’s their fantasy about me. I can do it if they’re really cute, but I don’t really want to do it. If I want to get laid fast, all I really have to do is *play what I look like* -- try to be what is expected of me based on my physique.

It’s stupid and horrible. It’s like going to the gym: it makes a difference. Go to the gym, get some muscles. Anybody can do it. It’s tedious, horrible and superficial, but.

When you’re an older effeminate man actually, you can play that. Denton talks about that a little bit, how he can go to a party and someone would take one good look at him and it would be evident to them that he’ll be the passive partner. But of course, aggressive top femmes also exist and that’s fine too.

I would just say for myself, I can’t complain about my sex life. The only problem with me is that I – to get very personal, I have a tendency to be, because I was in the closet for thirty years…

Is that true?

I came out at the age of 29. I spent my adolescence here in Canada and was in the closet until I was 28-29 and it really screws you up. So I would say I tend to be… I don’t think I’m a sex addict but I’m sort of compulsive about it. If you want to know why gay men act like adolescent girls, it’s because they didn’t get to be adolescent girls. You need to be sexual and romantic and have boyfriends and girlfriends when you’re a teenager. You need to go through that. You need to flirt. Romeo and Juliet, that’s normal.

OK but let me put this argument to you. Doesn’t it get tiresome? You’re in your late sixties, you’re cruising every weekend. Do you ever think, omg I just want stay home of a weekend, host a literary salon or something.

Ha, no, it’s my life.

Where’s the pleasure in it?

Danger. There’s an element of danger; with me it’s not a huge problem in the sense that I don’t court real danger very much, but there’s an element of that. You don’t know what’s going to happen, you don’t know who you’re going to meet.

I’m shy, believe it or not. I’m a performer, I can perform easily. Nothing I feel better about than this kind of thing where you’re interviewing me or I’m standing in front of a group or I’m teaching or acting, anything involving performing is fine. But one-on-one, going to a party and being with people, I am rather shy. Sex is a way to start the conversation. I’m not saying I become friends with people I have sex with, because I rarely do but the actual act of having sex is a kind of conversation. It’s being social. Sometimes I’m not very social and then I have sex. Then come the danger, the mystery, the surprise. Also it has a lot to do with rebellion. With not wanting to be told what to do.

Your Gloria Grahame is like that.

I think spending 28 years really policing yourself… I cant’ tell you what I went through. I bought dirty magazines, I threw them out, I tried to purge myself from homosexual desire.

Was your family super religious?

No, we were Presbyterian; my family wasn’t religious but I will say that I come from a family of ministers. My grandfather, my great uncle and one other person, all Anglican ministers. But it wasn’t that the family was very religious. Okay this is what I think is. I was a good boy. And there are good boys and bad boys. And I was a good boy. My boyfriend’s kind of a bad boy, and that’s one of the things that I find attractive about him. He was a naughty teenager; I wasn’t. My friends were doing LSD, they were having rumbles, this is the Sixties, I didn’t do any of that stuff. When I read my journals now, they’re all about trying to be not attracted to men. I can stop being attracted to men. Endless work. Endless self-examination. Now I think after so many years of trying to fight it, it’s hard for me not to just enjoy. The going out, the cruise, the chase.

The thing about cruising and anonymous sex is – it looks so non-verbal. People don’t default to language.

Yes that’s interesting, I have a lot of sex where not a word is spoken. A lot of queer people are not like that, my boyfriend is not like that, he has lots of friends he has sex with, but for me the two domains are separate. Whatever.

I am being honest with you because they are a lot of gay men like me. There are a lot of men like me. And some women. I mean, it’s like… it’s an important aspect of human condition which nobody ever talks about any more. And there was a time when I came out in the late 1970s, early 80s, when people were talking about promiscuity and alternative relationships and they were valorizing it and not demonizing it. And that’s just gone. So it is important for people to talk about it.

But it is a little more difficult [giggles] as you get older and less ambulatory. I always say I’ll probably end up going to a strip club in a wheel chair. I don’t really care.

I have to read this bit from the book because it’s very apropos. This is Gloria.“Those who are disgusted by love and sex will be a long time regretting a life they never had; or maybe they won’t regret it, which is even worse. No, I’m convinced that moralists live on morality the way chameleons (so they used to think, in olden days) live on air. Beauty and pleasure and happiness are just so incredibly rare that when they happen to you, you must experience them. You must. That’s my advice. I can die now. I can die now because I have lived – but I don’t intend to die any day soon. So there, moralists.”

This rings true. I think desire is good, I think this drive is good and vital. I used to think the opposite of this constant desirous state is contentment and tranquility, but I think its opposite is actually more akin to depression.

No I think you’re right. It’s a kind of hedonism, and it’s what Oscar Wilde’s favourite philosopher Walter Pater described as “burning with a hard gem-like flame”. That is what everyone should do. He talked about the senses and experiencing life and it was all very scandalous and sinful and shameful, and he was basically saying that it’s fine to have sex.

I firmly believe that a lot of the pain in the world comes from repressed people. I believe that there’s actually the old-fashioned evil, but I also think that a lot of the self-righteousness and the horribleness that people inflict on others has to do with their own unhappiness. When you’re a happy person, when you are fulfilled, as I feel I am, I feel I’ve had a very good life and am trying to continue to have one, you don’t really feel the need to inflict pain on other people. I think most people don’t, if they’re content. If they’re not content, they do sometimes have the need to attack and criticize and put down.

OK but what about the arguments like Marcuse’s ‘repressive desublimation’ (essentially, when something presents itself as liberation and is actually a new form of control) and Foucault saying that sexuality is not being repressed but continuously produced as a form of normative control through our endless talking about it and obsessing about it…

I’ll tell you a story about Foucault. A friend of mine here in Toronto used to know Foucault and had sex with him, they were fuck buddies. This may be an anecdote but we know that Foucault was for the longest time against “gay liberation”, and he actually had the experience of coming to Toronto with my friend and the thing that Foucault allegedly said was “When I saw the swaying asses on the Pride floats, I understood gay liberation.” I think he finally understood it being about having unashamed sex.

OK, yes, there is a rosy myth that if nobody was repressed, everything would be fine.

Right? And capitalism uses that.

Mmmyeah but I think we live in a very anti-sexual, anti-body, puritan society. I’m not saying that it’s the key to ending all repression…

But sex is everywhere. In the movies, advertising, the 24/7 internet porn.

Yes but I think that pornography is essentially anti-sex. You would have pornography, always, just like you will have S&M always – and they’re not necessarily bad things -- but our societal obsession with pornography and S&M and the infantilization of young women and all this, it’s all extremely fucked-up. It’s a type of Victorianism that we still live with.

It’s hard for me not to like porn because for a long time that was my only way of having a relationship with another man: through looking at a porn magazine. That’s before there were videos. But I firmly believe that this notion that we live in a pro-sexual society because there’s all this sex around is BS. There would be less sex around, if people had more actual sex. There would be less representation, exploitation of it -- because people would just be having it.

So the end result of this massive availability of commercial porn is actually a sort of desexualisation in real life?

Yes. There are young men who can’t have sex with women because they need the kind of scenarios they get used to where they’re being very dominant and the woman’s being very submissive, or they’re being abusive etc. -- they need that to be turned on. And they can’t find women who are like that and whose bodies look like that.

Life is social, a live interaction. That’s the way people get married, have babies, that’s how things are done. We’ve build everything around going to the marketplace and meeting people and socializing. So this switch is very scary.

A book of autofiction with ECW Press, Sad Old Faggot: A Novel (2016)

III.

There’s another bit that I wanted to read at you. Gloria is so good on this. “There’s something pathetic about the masterly male, if one looks at him in a certain context… [A]ll this kingship on the part of men – in other words all their imagined prowess and power – is pathetic and rather funny, and inevitably sexy. Look at how hard they try to personify all that they are cracked up to be.” Masculinity = a masquerade?

Speaking for myself, I felt all these various pressures growing up: do sports, perform sexually, achieve, all of these things were part of being male. A lot of people would look at me and say You should do football. And there was all this body correction. The way I talk with my hands. “Why do you use your hands like that, and so much”. I didn’t even know what they were talking about, I was just being myself. And when I went to acting school they couldn’t get past my mannerisms. Instead of allowing me to play women, fops, cross-dresser roles, my hands had to stop moving.

I was very conscious of that kind of policing, and when I did drag I could suddenly use this natural thing to be graceful and fluid in my physical expression.

I don’t think people know how oppressed men are. The way they express their frustration is through aggression because of course that’s what they’re supposed to do. It’s just a mess.

I think that being a man or being a woman is - whatever you are. It’s biologically decided which one of the two you happen to be, but from there really being a man or a woman is whatever you wish to be. You define it. I remember having a lot of insecurity about my father seeing a photo of me in drag in which I’m extremely beautiful. And it was all a bit fuzzy. Great big flattering photo of my face, I’d done my makeup right or something. It was in my sister’s apartment and she had it on her desk, and I remember my father picking it up, Who’s this? He couldn’t believe it. He knew about my doing drag, but I don’t think he ever saw me in drag. He looked at it… and I could tell he was frightened. ‘Coz I was pretty.

I remember talking to a therapist at some point, and I remember him saying Wouldn’t it be great if your dad could open up to the idea that there are different types of masculine men. Perhaps you could open him up to the notion that there are different ways of being.

How did he take it when you came out?

Oh the stories about my dad are funny. I brought him up from Buffalo to Toronto, to have lunch with me. He was kind of prepared. He met me at the Royal York, I remember him coming off the train. I said I have something to tell you and he said Don’t tell me. I said, What are you talking about. He said I know what you’re gonna tell me and there’s no need for you to tell me. Because I know. When I queried him he said he knew because I didn’t like throwing the baseball. This was his way of saying I know you’re gay. And after that there was an edict that I couldn’t talk about being gay around the house, and by then he was married to my step-mother. So when I came to visit him I couldn’t talk about it which was difficult because I was starting to run a gay theatre company and all this stuff.

He totally came around, totally changed. But it took some time. He lived to be 90 and before he died he was giving me books and saying Read this, it has a wonderful introduction where the author talks about how much he loves his gay son and it expresses my feelings completely.

My mother, I know that she blamed herself for my gayness. She believed in that popular theory from the 1960s and 70s – and my mother was a kind of a smothering gay men’s mother but I know a lot of straight men who have mothers exactly like that and it didn’t make them into fags.

And when I came out to my mother, she went Oh no big deal, sure, fine. But then I began to realize that she always resented it whereas my father reacted negatively at first and then began to embrace it. And he loved Ian, my partner, whereas my mother and Ian developed at best a grudging respect for each other.

IV.

I wanted to conclude by returning to Denton. Denton Moulton. Even his name is funny. But it all gets rather dark and sad near the end. It reminded me of The Pianist by Elfriede Jelinek.

I felt bad that it didn’t work out between him and the young guy. My partner was sad that they didn’t get together but I know that there’s a part of him that is irritated by the really old men and the really young boys situation. There’s a forty-year difference in Denton’s case. A) you have very little in common, and B) you have the capacity with that kind of age difference to completely dominate somebody. For instance, the relationship between Christopher Isherwood and his boyfriend who was 14 or something when they got together. And then lived in his shadow. He became a painter but his life was all about Isherwood. He turned into Christopher Isherwood in a way. Fine. Maybe that’s what he was, maybe he was an acolyte, a follower, but I have all sorts of problems with 65-year-olds and 25-year-olds entering relationships. I don’t think it’s really good for either party. So that was in the back of my head when I split Denton up from his former student.

But they could have at least had an affair? But no, you’re so cruel and so accurate: their fantasies don’t match.

I know I know… I tried to explain this to Ian too. The book is in part about how the man like Denton is not allowed to be happy. It’s what he’s saying throughout the book; people just want me to go to a hole and die. I upset them. I’m effeminate, I’m alone. I’m obviously gay.

Well there’s that terrible line, said more than once, “my place is lower than the ground and my fate is to roll in the dirt”.

Yeah. I think that’s the self-loathing that we live with as gay men quite a lot. And it’s very important to talk about that. Gay men go about being cheery – but they have a lot of self-loathing and people around them have a lot of disapproval and revulsion. I wanted at the end to be almost like an angry thing – Denton had to be a total outcast, someone who accepts his fate.

My work is totally centred around that kind of honesty. I’m honest about my life too. And so if I try to write a book that was acceptable, I can’t imagine what that would be like. I sort of tried. I tried to write books that were genre books, mystery books. I tried to sell a novel about JD Salinger, I took it to an agent -- that’s when I almost had an agent, or tried to get one -- and the agent said This character is just so narcissistic. I’m like, yeah, I think he probably was.

But let’s put the self-loathing business aside and end with this. What gives you joy these days?

The novel doesn’t finish on a sad note either. Denton finds Venus in himself. It’s an ecstatic ending!

I would say my creative work has kept me alive through all of this. Sex, very important. And my friends and my partner and all the people I love in my life. Those three things are important to me and they bring me a lot of joy. Those are all things that are worth living for.