For the Love of Hamilton. In this inaugural edition of a regular feature profiling those who have chosen Hamilton as home, we talk to playwright Sky Gilbert. Skip to main content
Celebrating all things Hamilton / Welcome Message
City Life

For the love of Hamilton

love of Hamilton

This regular HAMILTON CITY Magazine feature will highlight people, from all walks of life, who have embraced Hamilton as their new home. 

Outstanding and sometimes outrageous, the one-and-only Sky Gilbert once called Toronto home. But it’s been 18 years since he arrived in Hamilton, where he established the hammertheatre in 2007 at the old Ancient Order of Foresters building in the James Street North neighbourhood and was artistic director until 2018. Gilbert talked to HCM about moving to Hamilton, his recent theatrical work, upcoming projects and his sometimes, controversial opinions on LGBTQ+ issues and the challenges of gay life today in the city.

What attracted you to move from Toronto to Hamilton? 

It has a lot to do with my partner, I didn’t want to move at all. We had an apartment in Toronto, near the gay village, where I’ve always lived. It was sudden: ‘We should move to Hamilton.’ He took me to Hamilton on the bus to look around the city. My partner didn’t really like Toronto. Hamilton has a working-class vibe and he liked it. 

We moved here because he wanted to. I found it a bit scary at first but then we started to make friends here. And then at his urging, I started to do art here – a lot of visual plays at the (former) Artword Artbar that was on Colborne off James Street. It was very welcoming. Once I got started doing work here and making friends, it grew.

Now, I’m happy to be living in Hamilton. Lately, when I go to Toronto, the commute has become more difficult, and more irritating. Living in that atmosphere of glass tower condos, you can’t get anywhere, and a lot of the gay community on Church Street in Toronto is starting to disappear. I grew up in Don Mills so going downtown Toronto was exciting. I need the big city, but I love living in Hamilton. And Toronto is only a short ways away.

Sky Gilbert moved to Hamilton at the urging of his partner 18 years ago and has made the city his home. Portrait photos: Jon Evans

What neighbourhood do you live in, and why did you choose it? 

Now I live in downtown Hamilton – the Beasley neighbourhood. We bought our house for $90,000 in 2004, and now it’s worth seven or eight times that. We wanted to move downtown and there was actually a gay culture in downtown Hamilton when we moved here, a gay book store, some bars. So that was part of it. And I wanted to be near the bus and trains so I could get to Toronto when I needed to.

What do you love best about Hamilton? 

There’s a definite lack of pretentiousness in Hamilton – and the working-class culture that has helped define Hamilton was a big attraction. What I really like – I’m basically an uptight white guy – I’ve loosened up so to me – there seems to be a relaxation around a lot of things, around sexuality. Believe it or not, a lot of people assume that working-class people are homophobic, but that’s actually not true, it’s a lot more complicated than that. In my view, middle-class people are just as homophobic, but working-class people seem to be more honest about it, which means you can talk about it. Middle-class people lie about it. And in Toronto, you have extreme poverty and extreme wealth. It’s very off-putting. Where here in Hamilton, you have a mix of working and middle-class people.

You left behind a very successful legacy including being co-founder and artistic director of Buddies in Bad Times Theatre. Your recent play Pat and Skee was a tremendous success at Theatre Aquarius earlier this year. So, what’s in store for Sky Gilbert — do you have any theatrical plans for the coming year? 

I’m currently working on two projects in Toronto and one project in Hamilton. It’s pretty amazing that I can actually do this. I’ve approached Mary Francis Moore, artistic director of Theatre Aquarius, with a new idea. And she approached me with a new space at Theatre Aquarius — a smaller space but it inspired me. So, I’m proposing a really queer play for Hamilton, a kind of an experiment for Theatre Aquarius, so we’ll see what happens. 

I have two projects in Toronto. They’re both really out there. I received a Canada Council grant for one of them before COVID. It’s called Kink Observed. It was written in response to what I would call the demonization of gay male sexuality that happened with the Bruce McArthur murders. You had to read all the stuff about him. He hung out at the bar I hang out, The Black Eagle on Church. OMG, the sub-text that all these men got killed from the Eagle. I think it’s the best bar in Toronto now in my view, and the gayest gay bar. So, the play is trying to make people understand gay male sexuality at a time when I don’t think people talk about it very much. So that’s what Kink is. The other play is a collaborative project with a small group of actors and some creative people who will design it. 

I’m also working on something called Who’s Afraid of Titus – which is my experiment in Shakespeare directing, which is something I want to go into. I’ve written two books about Shakespeare theatre, the recent one I’m waiting to see if and when it’s going to be published. So yes, one of the ways I want to expand my horizon as a director is to direct Shakespeare. We workshopped this play a year ago, but we didn’t get to put it on because of COVID. But it was very exciting. It came from the performers and they want to keep working on it. Hopefully, we’ll get some funding for it.

What in Hamilton surprises and delights you? 

What I like is that the arts and music is really prevalent and has been for years. The great galleries that were on James Street North like the You Me Gallery and Hamilton Artists Inc, which have been here for a very long time. The music scene — you can feel it in this city. The musicians who’ve been working and living here for years, and if they’re living here, it’s because they want to do their work. It was one of the big surprises about Hamilton – the extent of the music scene.

I’d also say that the Hamilton art scene is very much connected to visual arts and music. The theatre scene is mainly amateur theatre. I have nothing against amateur theatre but it’s a different thing from professional theatre. So, when I came here, I spent a lot of time fighting to get the arts council in Hamilton to give funding to artists for theatre. I had to literally try to educate amateur theatre people who would say, ‘Why do you want handouts from government?’ I told them a lot of work is done by grants. It’s wonderful to have a live amateur theatre scene. It would be wonderful to have a professional theatre scene. 

What would you like to see change, grow, and improve in the city? 

I would like to see the people of Hamilton celebrate the essence of Hamilton more, instead of saying ‘hopefully we can be like Toronto’. Hamilton has something else to offer. You have this working-class milieu, this sense of real artists doing real work. And there’s still space to be had, it’s relatively inexpensive. Why not celebrate that? 

When American filmmaker John Waters came to Hamilton, he really liked it. He compared Hamilton to Baltimore or Brooklyn — compared it to the idea of a city adjacent to a big city. You can live in Brooklyn. You can do art in Brooklyn. It’s almost impossible to live in Manhattan, and you can’t afford to do art in Manhattan. I think that’s important to be yourself. Be Hamilton. 

What is one thing you would brag about Hamilton to outsiders? 

The physical beauty of Hamilton. It is far more beautiful than Toronto – look where Hamilton is located. Toronto has the lake, but Hamilton has the lake, it has the bay, Cootes Paradise, the Mountain Escarpment, the valleys, and so much more. So, it’s the physical beauty of this city which never goes away. I used to see Hamilton driving along the QEW to Buffalo, where my dad lived, and you’d see the bridge and the factories and smoke and think, ‘Ugh, Hamilton.’ That was the way we always thought of Hamilton. Then you drive into Hamilton along the 403 near Cootes Paradise, and you think ‘Wow, it’s so beautiful.’ So, the arts scene, the immense beauty of the city’s geography and the houses. The beautiful old houses in Hamilton. They’re not going to be turned into condos like what they’re doing in Toronto. They are literally razing the history of Toronto …Toronto’s history is disappearing.

Hamilton’s LGBTQ+ community has grown over the years but there is no central “gay neighbourhood” like there is in Toronto. The WELL is the first new LGBTQ+ bar in Hamilton in years. Is this a Hamilton thing? 

It’s like this everywhere…everyone’s online. People have less sense of community. And I think there’s a real problem for gay men. I come from the era of meeting people in person, not online. I’m not a fan. There’s a lot of people still closeted. A lot of people don’t want other people to know they’re gay, a lot of people who are still ashamed of it as much as people like to pretend everything’s all hunky-dory. So basically, gay men have gone into hiding again – online. That’s the way I feel. I’ve been ranting and raving about this for years and it doesn’t make me very popular in the gay community. I call it the assimilation of gay life and culture. A lot of gay people insist there’s nothing different with them from straight people except the fact they’re attracted to a person of the same sex. I just don’t agree with this. I’ve worked on gay culture for years. I’m part of it. And I think there is such a thing. And of course, I’m ambivalent about it. Gay bars, drag and pornography aren’t perfect but they’re part of our culture. It’s not going away. Men and women will always be attracted to those aspects of gay culture.  

The trans community has taken over the politics. Part of it is that gay men never took their ownership of gender. When I was at Buddies, I was a drag queen. And that caused me a lot of grief in the gay community. People would ask me why Sky Gilbert is representing us as a drag queen and a slut, and that I should be a nice guy in a suit. Some found it disgusting — Divine was the old view of gays, and now we’re in a new era and we’re not like that. I’ve always been very open about doing drag. I love doing drag, but I have this beard now and I don’t like drag queens with beards. It’s just not right. A lot of gay men still have ambivalent feelings toward drag. This is part of the reason you don’t have a downtown gay culture. That’s my analysis why you have a lot of gay men living like straight people in Hamilton, but I’m just not that person.

Sky Gilbert says drag isn't always embraced in the gay community. Photo: Submitted

What’s your take on Hamilton’s LGBTQ+ community? 

Hamilton’s LGBTQ community has the possibility to be much more open and much more interesting because of what I said about the working-class attitude to sexuality and tends to be more open about sex in general. The former Embassy Club was beautiful in its early days – a world-class nightclub in an old bank, with a stunning chandelier and balconies, pool tables, dancing, etc. It had such a diverse crowd, everything from baby dykes, old fags, drag queens, some straight people, and others, all mixed up. This only happens in the smaller cities. People came there from all around. A lot of gay bars in Hamilton used to be more like (restaurant) places with bright lighting. The Well is really unpretentious in a very good way, so there’s hope for Hamilton’s gay community. 

I don’t think we’ll ever see a lot of gay clubs again, but we’ll see. It’s a good question. I have a very pessimistic view that we’re going to go through a period – we’ll see how much oppression comes from the repression. I just wrote an essay for an online publication about the new homophobia in the trans movement. I just read a book that suggests gay liberation is fundamentally racist. There are people in the trans movement and gay men that don’t want to stand up for gay rights. People used to come up to me in Toronto and it really meant a lot. They would say, and sometimes very conservative gay men, they’d stop me on the street and say, ‘I could never do what you do, but it’s really important that someone is doing this – saying I’m a drag queen and a slut. Someone has to push the boundary.’

But if everyone’s sitting around and saying, “We’re not like that, we’re really nice people, we don’t do anything bad.” People think they can appease the haters. It doesn’t work, the haters will still hate. They won’t back down.  We may go through a period of protest – it will be interesting to see if all the oppression and repression will finally make the gay community stand up again and say this is who we are. 

Sky Gilbert says he loves the lack of pretentiousness in Hamilton and working-class culture that has helped define the city
was a big attraction. Portrait photos: Jon Evans

A Renaissance Man 

A successful playwright, writer, director, filmmaker, actor, poet, professor, a proud gay man — and occasionally a drag performer — Sky Gilbert was co-founder and artistic director of Buddies in Bad Times Theatre in Toronto for 18 years. His plays have been produced in New York City Chicago, San Francisco, Houston, Phoenix, Vancouver, and Montreal. Gilbert has received three Dora Mavor Moore Awards (Toronto's "Tony") — for playwrighting; the Pauline McGibben Award for theatre directing, and was the recipient of the Margo Bindhardt Award (from the Toronto Arts Foundation), and the Silver Ticket Award (from the Toronto Alliance for the Performing Arts). In 2014 a street was named after Sky: Sky Gilbert Lane.

Gilbert started making films in 1990 and has written, directed and produced three films which have played at film festivals around the world, including Hong Kong, London, San Francisco, L.A. and Melbourne. He has published five novels and his fourth novel, An English Gentleman, received Canada's ReLit Award in 2005. In 2006, Dr. Gilbert was named University Research Chair in Creative Writing and Theatre Studies at the University of Guelph. Sky Gilbert is a controversial but creative, artistic force in Canada. 

If you'd like to be featured in For the Love of Hamilton, please contact

Arts for All