Tell Shelley Anne: Interview With Grae Phillips

By Shelley Anne Baker

This interview originally ran on TGForum and was reprinted here with Shelley Anne’s permission.

Born in Montreal, Canada, Grae Phillips came to national attention in the ’80s and ’90s by appearing on over a dozen talk shows, entertainment programs and news broadcasts. Among them were the Jenny Jones Show, Geraldo Rivera, Sally Jessy Raphael, Montel Williams, Evening Magazine, News for New York, 9 Broadcast Plaza, Jane Whitney, Real Personal with Bob Berkowitz, City Magazine, and the Phil Donahue Show. The Donahue appearance brought in its highest-rated show that year.

For decades, Phillips performed in New York City’s top nightclubs and cabarets including an Off Broadway One Woman Show at the Nat Horn Theatre. The National Enquirer wrote a featured article about Phillips’ beautiful singing voice and branded him “A Real-Life Tootsie.”

At present, Phillips is filming a documentary on his extraordinary life journey entertaining as a woman and all the challenges that it brings.  The Grae Phillips Album was released in 2022 and can be streamed on Spotify, Apple Music, iTunes, Amazon, Pandora and Deezer.

Shelley: How did you enter the world of drag performing?

Ms. Phillips: It came about from a singing audition I had done for a new Broadway show called Taxi Dancer held in New York City. I received a phone call shortly after the audition from the producers and they scheduled a call back for me. However, when I met with them, they had something quite different in mind. The year was 1983 and Boy George had top hits such as Karma Chameleon, Miss Me Blind and It’s a Miracle. They felt that I had a unique singing voice, and they wanted like to develop it. However, they wanted to produce me as a woman and go further than Boy George. I remember thinking, what is so scary about becoming a woman? Wouldn’t it be an awesome experience? Besides whom will ever know as I am thousands of miles away from my home, I laughingly thought.

Shelley: Has your career been as exciting as it appears?

Ms. Phillips: Absolutely. In the beginning I had no idea if I could pull the illusion off. They tested me in several venues. I remember walking on stage at the Helmsley Palace in New York with the Stewart White Orchestra and thinking, can this be real? Can I really do this? The room was filled with 700 dinner guests, and I heard a thunder of applause ripple through the ballroom. I suddenly realized the applause was for me. I had just been announced as a singer from Atlantic City, and the reality hit me. Yes, this is real, and I took to the stage.

Shelley: You have assembled quite an array of costumes. You must have a large closet.

Ms. Phillips: Yes (LOL). They could take up an entire room easily. While photographing them for my documentary, I realized that each one had a great back story and an emotional memory for me. Costume #28 is a gorgeous black slim fitting dress designed by Mancini (not the musician) and I wore it several times including my engagement at Studio 54, where I had a devastating run-in with Boy George. Or Costume #42, I wore while singing at the old “Bon Soir” club (then called Sanctuary) where Barbra Streisand got her start in 1962. I spent many evenings there after my performance chatting up a very young and sweet Chastity Bono, before she transitioned to a man.

Each time I unpacked a gown, a memory would surface. A lime-green sequined jacket reminded me of a disappointing performance I did for Andy Warhol and yet another was perfect for an exciting night I received an award for the Advancement of Theatre in New York. The memories kept coming. View my costume gallery online.

Shelley: From my perspective, you have been quite an inspiration to others. 

Ms. Phillips: I have been fortunate to receive quite a bit of mail over the years, especially after performing on the Donahue Show. The letters were wonderful, and I had the opportunity to meet many of the girls at the Southern Comfort Conference of Crossdressers at the Sheraton Hotel in Atlanta. I was asked to be a guest speaker and headliner at the Conference in 1998, and it was a wonderful experience.

At the conference I met many professionals, lawyers, businessmen, even politicians. I identified with these men and women for the courage it took to explore their own personal natures as well as taking the risk to be themselves in a world that can be dangerously judgmental.

In the final moments of my performance at the Gala dinner, I decided to do a Victor/Victoria and pull off my wig. It was symbolic, because out of the hundreds of men and women I had met over the weekend there were still some that seemed a bit shy and insecure about their looks. They felt they were not pretty enough and a feeling we all experience. To me they were all gorgeous and I wanted to remind them that the makeup, the wigs, the dress, the shoes are all external aspects and what is important is what is inside, and “how” the experience feels. It is just a means to an end, and that end is how we express love, to each other and towards ourselves.

Shelley: Prior to performing, what was your personal life like with family, and friends? 

Ms. Phillips: Interesting enough, I come from a family of females. I have a twin sister, an older sister and two younger sisters. My mother was very special, very beautiful and loving. My father dismissed me at a very young age, and eventually passed away from his alcoholism. Today, they continue to be very supportive, and we are all very close.

Shelley: Obviously, you love music. What specific musical training have you had?

Ms. Phillips: I began performing quite young. I attended a Theater College, also trained as a vocal major at a second college and had been studying dance with Les Ballets Jazz in Montreal for seven years. I began singing in nightclubs and concert venues by the age of 17 and at that time I was fortunate to win a recording contract with the group Crossroads of the CJAD radio station search for Canadian talent. I recorded my first single at Listen Studios in Montreal. The name of the song was Broken Dreams. Ironically my dreams would eventually be broken at that young age but only to be healed when I was reborn as Grae Phillips and then those dreams started to come true.

Shelley: Is New York City your favorite city to entertain in?

Ms. Phillips: New York, Aspen, Toronto, Montreal, Atlantic City, all are favorites and wonderful cities to explore. Of course, I spent the most time in New York, so I knew it best.

Many nights after my Follies show at club Tatou on East 50th St., I would hail a cab and go out for dinner. It was always late, around midnight and since I was dressed as Grae it was fun to experience the city on this level. When the full realization hit me that I could pass completely as a woman, the world opened for me. We would head over to restaurants like Chez Josephine on west 42nd which was a place I adored with its French European atmosphere. Jean Claude, the proprietor would send over champagne, and we always got a great table. I had started a fur collection that I would wear out. I loved a good reveal, and when the maître d’hôtel helped me remove my coat/fur I would always have something on worth noticing.

If we finished early enough, we would head over to the Crystal Room at Tavern on the Green among the tiffany-stained glass and baccarat chandeliers. My favorite drink there was a very dry vodka martini, or two or three. The Russian Tea Room on 57th was fabulous for late-night dinners as well, and all the Broadway crowd would be there. One night I wore a red fox trimmed fur coat from Morgan’s furriers with a red sequin flapper dress under it. It was a unique time, a magical time and it often felt like I was part of a Woody Allen movie.

Shelley: Other than drag performing, what is one thing people would be surprised to know about you?

Ms. Phillips:After leaving New York I took a four-year break from entertaining and attended university studying psychology. I switched programs and received a diploma for Computer Animation in Cinema and television from College Inter-Dec.

Shelley: Any final words?

Ms. Phillips: Thank you, Shelley Anne it has been a pleasure to share my story with you and your readers. I created a Facebook page this year documenting my experiences and I post each week. I am inviting your readers to visit. They can view my costume gallery and read the stories associated with each outfit as I post new blogs. I love to read comments. Click here to visit.

I wish our entire community a wonderful holiday season and may 2023 [originally written in 2022] be the best year yet for making dreams come true.

Editorial update: I also interviewed Grae, which will follow tomorrow. In hindsight, I now know she was the person I serendipitously watched on TV in my youth, not wanting anyone to know what and why I was watching. Grae will be involved in filming a documentary on her life next year and I am under consideration (no pressure there…) to participate (sure I have co-starred with Adam Driver and Greta Gerwig). In all seriousness, it would be such an honor. Ladies like Grae made me know, before Al Gore invented the internet, that there were others like myself in existence. Her courage was a guiding light! More tomorrow….

And more of Shelley Anne to come!