Kaleb Robertson has been dreaming up new and creative events here at the Gladstone since 2005. He’s reached legendary status at the hotel, having held a slew of roles, ranging from server to Director of Cultural Programming, DJ, drag performer, Trivia host extraordinaire, and even the MC at our Staff Christmas Party. The Gladstone wouldn’t be the same without him.
Kaleb sat down with us to chat about his history at the Gladstone, his love of hosting and performance, and his popular event series, Music Bingo, which happens every Wednesday in the Melody Bar.
You’re a very special member of the Gladstone Hotel, and our most versatile host and performer for events. Could you tell us about your history with the Gladstone and how your role has evolved over the years?
I’ve always lived in Parkdale, so the Gladstone is a fixture in my life. My first shift with the Gladstone was in December 2005. I worked in the cafe, which at the time, did not have a kitchen or food service (though we did have one fancy coffee machine that remains today, so I’m probably quite the expert with it). I worked there for about a year and a half, and while there I started throwing events in the ballroom as well as attending a lot of the old classic events such as Hump Day Bump and Fox Hole. Then I left to do other things for a while, and I came back through a request — “Hey could you come help us out a couple hours a week to do social media?” Five years later, I had become the Director of Cultural Programming, a role I created myself. I mean, if nobody’s going to give you a fancy title you’ve gotta make your own up.
How did you decide to start throwing events?
A lot of ideas came out of being in this creative space. So many people with fun ideas! You throw them around and sometimes stupid sounding ideas end up being really fun. One day we were sitting around the office, talking about our favourite 90s television shows, and thought, wouldn’t it be funny to do a 90s show trivia night?
When did you realize you were really onto something?
We tried it out, and right away the room was packed. It was overwhelming. Once we had a Seinfeld room crammed with over 250 people. We were doing the Elaine dance-off when somebody tweeted from the back of the room, “I’m at Seinfeld Trivia and Scott Speedman just sat at our table”. Then I was approached by Harper Collins, because they were releasing Jason Priestly’s memoir and they asked if we could do a special trivia night for it. I jokingly replied, “Only if he’s going to be here!” Two months later, I was hosting our trivia night in a room full of 90201 fans with Jason Priestly and Brendan Walsh on stage with me. Jason Priestly and I actually held hands. That night was probably one of the biggest highlights. 3.5 years later, I’m still doing TV trivia and people are still requesting shows and asking when you’re doing Party of Five again. Who knew that this was going to be my life, but it is!
Can you tell us a bit more about what it was like growing up and performing?
I feel like I’ve always been a performer, even though I’ve never been professionally trained. First, I performed the gender role according to expectations in this world. The stage stuff came later. When I moved to Victoria for University, I realized there was this world of drag where I could gender-bend and have fun. This all kind of culminated into “The Me Show,” a performance I did at Rhubarb at Buddies a few years ago, where I explored gender in general, and specifically in the ways I performed it, both in my day-to-day life, and on stage. That was about 5 years ago, I’d like to go back to it, as there’s a lot of stuff I want to re-visit.
How did your drag character Miss Fluffy Soufflé come to be?
Miss Fluffy Soufflé is my alter-ego. She came at a time in my life when I needed some inspiration. I entered a competition on Church Street and it turned out that all my fears about drag and the gaybourhood were true. It was a really racist, misogynist, fat-phobic environment. But I also had a lot of people appreciate what I was doing, even though it started out as really trashy and basic. But that was kind of the point. I wasn’t going in with amazing makeup and this glamorous persona, because that’s not me. I glue stuff to my face to make it sparkle. I wear clothes that sometimes I get at Forever 21 or sometimes that I’ve created, and I entertain people.
What do you enjoy about performing in drag?
It’s all about putting myself on stage and other people getting to feel comfortable with that. Or if they are uncomfortable, asking themselves why they feel uncomfortable.
This year it took me out of town, to Sudbury, to DJ their Pride prom, which was amazing. I hosted Toronto’s Pride Prom at Buddies on Pride Week, and a drag event at the Yorkville public library where I read storybooks to children. At this point I feel like Fluffy has now developed from this raunchy sexualized person to someone who has access to youth, to show them that you don’t have to be the best person at makeup, or have a cinched waist and big fake breasts to be on stage and do performance. I just am who I am, so getting to people that way has been really cool.
What do you love most about hosting and performing?
My favourite part of performing is the political aspect. I’m openly queer and trans, and I’m fat, and I dance up here all the time. I want people to see this person on stage — this body, and this identity — and I also want them to have a fun time. If someone who has never met a trans person before is at first like, “Who is that?” or some cases, like, “What is that?”, by the end of the a four minute song or night of trivia, they don’t care who I am because they’re having such a great time. When I’m hosting, it’s my space and I’m creating a safe space.
What does safe space mean to you at your events?
A safe space means I’m not saying anything racist, homophobic, or ableist.
So for example, Music Bingo’s all about fun, but I will still call shit out if it’s relevant. If Cher’s “Gypsy’s Tramps and Thieves” comes on, I will say, “This song could never be made now, could it?” or, “This isn’t OK is it?” I will talk about BLM, and Orlando, and rape culture, all under the umbrella of having fun at an event.
A couple weeks ago, I refused to play the song “Blurred Lines.” At first I said, “I’m going to skip the next song,” and everybody went, “Ooh, why?” I told them the song, and mentioned the recent Stanford rape case, and that there are no blurred lines, and it’s bullshit, and people applauded. Afterwards, somebody approached and said, “Thanks for doing that.”
I also feel very lucky to have a place like the Gladstone where I know everybody is gonna have my back. I feel that way about putting on events here, attending events here, and being on stage. I feel the same about inviting people into the space, with the washroom policy being that people can go into the washroom that they identify with, the fact that there are also gender neutral washrooms, as well as the physical accessibility of the space. No matter the event, everyone is welcome at the Gladstone, and if you’re not down with that you’re asked to leave.
Who comes to Music Bingo? What is the crowd like?
It has been interesting because such a diverse group of people comes. We celebrated both a 72nd and a 19th birthday last week, and an ESL class has come a couple times, and big groups of friends. People sometimes come in and they’re nervous, because it’s their first time, but as soon as you put down the bingo dabbers they get really excited because they don’t usually get to play with bingo dabbers.
What do you think the audience enjoys and takes away from it?
People always walk out with a smile and an Instagram picture of them and their friends having a good time. But hopefully not a hangover!
For a lot of people who come, Music Bingo is their first time at the Gladstone. Then they find out about all the other events we do here in the Melody Bar on a weekly basis, or about the 37 artist-designed hotel rooms.
You’ve seen it all at the Gladstone. Can you think of a story or memory from your time with us?
Having been at the Gladstone for so long, not a lot surprises me. You see people in drag in the middle of the day, or an opera that moves around the building, or one of the world’s greatest graffiti artists, Sheppard Fairey, making an artwork on the back of the hotel. Everybody that comes here has stories. People get excited about all the celebrities that have been here. It could be an artist that nobody would recognize except for the person working the front desk, who happens to love his paintings. Or it’s Patti Smith staying here, or Sandra Bernhard having lunch in the cafe. For all these people it’s just a super casual place to be.
But one fond memory I have is from when I was a server. I used to have to come in super early, and since not many people arrived at 6am, I would flip over an ice bucket and relax. But I always knew I had to wake up properly when Hank the Gladstone Cowboy came in, because I’d hear the click of his cowboy boots as he arrived. Hank worked at the Gladstone for years and was known for singing Karaoke and operating the elevator. I’d hear his heels and perk up so he could get his muffin and coffee, tip the remainder of his change, and be offended if you tried to give it back. It’s also people like Hank who have contributed to making the Gladstone such an amazing place and memorable place.
Also, when Jason Priestly and I held hands.
Thanks so much Kaleb, and see you at Music Bingo, Wednesdays from 7-10pm in the Melody Bar all summer long! RSVP to the Music Bingo Facebook group here.