Oprahphilia, by trey anthony
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Oprahphilia, by trey anthony

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Illustration by Sasha Plotnikova/Torontoist.


A veteran of the Toronto theatre scene, playwright and producer trey anthony is best known for turning her one-woman play ‘Da Kink in my Hair into an international success story, selling out the Princess of Wales Theatre in Toronto, as well as shows in London (U.K.) and San Diego. She has earned four Doras and four NAACP awards and created a national television series based on the play. Trey is currently producing her brother’s debut play, Secrets of a Black Boy, which opens September 23.
Since she was a child, trey has idolized Oprah Winfrey, whom she credits for much of her success, but the two had never met. Winfrey was in town this week promoting
Precious, a film she executive-produced with Tyler Perry, and trey was determined to connect. She recounts the experience for Torontoist.

I had priority seating for the screening of Precious, and before I got there, one of my industry friends called me and said, “I have to let you know that there’s a private reception with Oprah before the film, and you need to get into that. But I don’t know how to get you in.”
The screening started at 9:30, but I got there at 8 and locked eyes with some guy wearing a headset. His face lit up, and it turned out that he recognized me from ‘Da Kink In My Hair—so I thought it was my chance. This is me being proactive: it may have involved a little bit of lying. I said to him, “I hear there’s a VIP reception happening, and I need to be at it.” So, it wasn’t really a lie, because I did need to be there. Technically.


“Oh, you’re looking for the VIP reception!” he says, assuming that I had been invited. “You have to come with me, and I’ll bring you to the green room.”
My mother always taught me to act like I was supposed to be somewhere, even if everybody knows you aren’t. I walked into the green room and spotted the co-director of TIFF, whom I know, and he looked very stunned to see me. He walked over to me and kissed me on both cheeks, clearly surprised.
I knew my ass wasn’t supposed to be there, so I tried to redirect his attention. I said, “Hey, how’s your family? How’s your sister? I’m so proud of you! What a wonderful program this year!” He was responding, but I could see the wheels turning in his mind, and he didn’t have the heart to ask me to my face how the hell I got in there.
Then, out of the corner of my eye, I spotted Oprah’s hairdresser, André Walker, and her makeup artist, Reggie Wells. They waved me over, saying, “Hey, we didn’t know there’d be more black folks up in here,” and ended up being very friendly and incredibly personable.
When Reggie asked what I did, I told him that I was one of the first African-Canadian women to have her own prime-time show on a national network here in Canada. He was very excited for me and encouraging, but as I was having this conversation, I could sense a rumbling happening off in the corner. I looked over and could see the co-director talking to two women on headsets, and it was clear my time in Oprah’s atmosphere was coming to an end.
The two women walked over. “Um, do you have verification to be here? This is a private event, and you need an invite to be here.”
I pretended to be quite stunned and made this whole big show of looking frantically through my bag for the so-called invite that I knew I didn’t have. Since I knew I would find no ticket, I became bold and acted like I was being wronged.
“I’m trey anthony, and I have my own TV show, and if there is a VIP event for the entertainment industry, I feel like I should be here!” It was all for show, but I did have a point: like Andrea Case, Karlene Nation, and Jean Carter, I’ve accomplished a lot as a Black woman in the Canadian entertainment industry. Here is a reception for a Black entertainment icon, and none of us in the industry were invited to represent our local Black entertainment scene. Aside from Oprah’s hairdresser and makeup artist (and the co-director of TIFF), I was the only person of colour in the room. And I wasn’t supposed to be there.
I pointed at the co-director. “Ask him! He knows me!”
And they said, “Yes, well, he’s the one who said that we need to get verification from you.” So, I smiled meekly, knowing the game was up, and was escorted out in deep shame.
Back to my seat. Kicked out. But when Oprah finally came out to introduce the film, I was in my glory. My idol of twenty years was right there. With three hundred people between us. I’ve come this far and she’s sitting right there, and I can’t meet her. So I let it go, thinking that there was a bigger purpose in store. God wanted it to happen another way and at another time.
As I was watching the movie, I realized that I needed to go to the bathroom. My partner Lori told me that the film would be over in twenty minutes, and that I should hold it. There was a thing in my head, however, that said, “Go. To. The. Washroom.” I left, and there were restroom signs pointing both upstairs and downstairs. I went up.
Because I wanted to look really great that night, I had on two pairs of Spanx and a full-body girdle. I thought that if I had the chance to meet Oprah, I needed everything to look on-point. To go to the bathroom was a big deal while wearing all that, so it took me quite a bit of time, and while I was wrestling with my undergarments, I thought to myself how funny it would be if I met Oprah Winfrey in a bathroom while trying to do up my Spanx.
As I left the washroom, coming up the stairs was Oprah Winfrey, shoes in her hand, and followed by her bodyguard.
It was me, Oprah, and the bodyguard alone in this small little space. Oh my God, trey, pull yourself together.

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Oprah Winfrey and Tyler Perry arrive at Roy Thomson Hall. Photo by mrvmedia.


I turned to her, and I don’t know where it came from, but I declared, “Ms. Winfrey, my name is trey anthony, and I am one of the first African-Canadian women in Canada to have a prime-time TV show on a national network. I want you to know that I used to rush home every day to watch you, and I feel that if it wasn’t for you, I wouldn’t have a TV show, because you made me believe that it was possible for a woman who looked like me to be on TV. You are my mentor and such an inspiration from afar.”
She shook my hand and said, “Thank you. Good for you. Good luck.” And then she headed into the washroom.
I watched her go and tried to figure out what I was going to do next. I had to do something important.
“Ms. Winfrey!” I called again to her as she returned, taking out a DVD I had in my purse. Preparation; you have to be prepared for any opportunity. I may never have this chance again in my life, and I need to be bold. I want Oprah to see the documentary on ‘Da Kink, and I want her to know what I’ve done. I asked if she would accept the DVD.
“Yes! Thanks, trey.”
As this was happening, my best friend Rachel happened to come up the stairs and witnessed my Oprah moment, and as soon as it had begun, it was over.
Oprah took my DVD and brought it back to her seat. The only thing that was running through my mind is that my two-decade-long dream had finally become reality. This meeting was something that I had affirmed to myself for so long.
As Oprah descended the stairs, Rachael ran to me and we fell apart, trembling and shaking.
I believe in treating people with respect and living in a truthful, positive, and honest way because I feel like the universe rewards those who do so. This, I believe, is how this meeting happened.
Twenty years. Twenty years, Oprah, and it finally happened.

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