Meet James Haake: The Oldest Working Drag Queen

James "Gypsy" Haake

Dancer and actor James “Gypsy” Haake is, according to his Twitter bio, the world’s oldest working drag queen. After a career in show business, he came out of retirement in his 50s to try on his first gown and now, at 86 years old, he still commands the stage with his unique brand of drag-meets-comedy and has no plans to stop anytime soon. Below, Gypsy tells me about his long-standing career, celebrity encounters and what it’s like to live separately from his onstage persona.


hen the curtain opens and I come onstage at Oscar’s Café & Bar in Palm Springs, California, the audience gasps. I parade around in my cobalt blue makeup and beautiful Bob Mackie gown. Then I open my mouth and usually start with, “Ay, how you doin’?” or one of those New York hollers. The audience just goes nuts. They expect me to have an artificial girl’s voice, so when they hear mine, they just don’t know what to do. My gowns are beautiful, but my face will kill you.

I created this character that talks like a man but dresses in really gorgeous outfits with big hats and jewelry. In my mind, I’m not wearing a dress — I’m wearing a costume. The show is a structured theatrical production where I, as Mastress of Ceremonies, introduce actors who impersonate celebrities. That’s what makes our show a bit different from other drag shows.

I never studied comedy, and I was never interested in doing stand-up, but it just came naturally to me with what I do. I’m off the cuff, off the top of my head. Audiences carry me a lot. I can look at the audience and see the history of some of these people because I’ve been around that long. I was in New York for Stonewall and in L.A. for all the AIDS horror in the ’80s. I’ve been around and around. This year, I’m celebrating 67 years in show business, from the stage to films to TV.

I grew up in Morristown, New Jersey, outside of New York City. My family was rather dysfunctional. I was adopted. My mother had two children after I was two years old, and my father put me back in the orphanage each time she got pregnant because she didn’t really want me there. When I was going into high school, I had to live with some neighbors because my father beat me up so much. I do have an adopted niece who is a wonderful woman, so she is my family. I’m not bitter about anything. I wasn’t bitter when I was 14, so I’m not bitter at 86. After all, I’m very lucky.

In those days, in high school in the ’40s, that just wasn’t done

Beginning my freshman year, I would spend my summers at the Paper Mill Playhouse in the town next to mine. I took dance classes as well — tap, jazz, ballet. In those days, in high school in the ’40s, that just wasn’t done. I think there was only one other guy in classes with me.

After I graduated from high school in 1950, I went to an open call in New York for a group of dancers. The company hired chorus boys and girls called “gypsies” — which is how I got my name, Gypsy — to go on tour with famous people and on Broadway. I danced for Broadway musicals and on tours all over the country and in Europe until the early ’60s. Then in the mid-’60s, I got the chance to headline and open my own cabaret, called Gypsy’s, in Manhattan. It became very famous, but when disco and Studio 54 came in around 1978, nobody was going to cabarets anymore. So I retired at a young age, at almost 50. I came to L.A., never thinking anything else would happen.

In 1980, a nightclub and showroom opened in West Hollywood called La Cage aux Folles, named after the movie that had just come out and won best foreign film. The club opened to rave reviews, and I came out of retirement to headline it. I had never really done drag. I had never even worn a dress before; in my club in New York, I had just worn tuxedos. I decided to never wear wigs or boobs, but I’d wear fabulous gowns and six-inch high heels. During the run of La Cage aux Folles, my legs were insured for a million bucks. I still have great legs for 86, if I do say so myself. I modeled my makeup on Agnes Moorehead in Bewitched. I have all this cobalt blue stuff on the eyes and false eyelashes. I’ve been doing that all these years.

By 1983, famous stars like Lucille Ball and Lana Turner had already had their own tables at our club. On Christmas Eve that year, Mel Brooks and his wife Anne Bancroft came to see the show. Mel said, “How old are you, Gypsy?” I joked, “Oh, I’m a baby. I’m 51 years old.” He said, “You’re never too old to become a movie star, and I’m going to make you one.”

And he did. Mel Brooks signed me to co-star with him and Anne in the movie To Be or Not to Be. I played Anne’s dresser, and she coached me every single day for six months during filming. They could’ve hired a coach, but instead she did it personally. We were in lots of scenes together, and I had a big dance number in drag with Mel. My name was submitted by the head of the studio to the Academy for a Best Supporting Actor Oscar. I didn’t get it, of course; I didn’t even get the nomination. But my name was submitted. Since that movie, I have done 20-something films and about 100-some television episodes.

The biggest stir in my career was last summer when Miley Cyrus decided to hire a group of older people for her music video “Younger Now.” I was the second oldest person cast, and I learned an awful lot from that 24-year-old superstar. I also danced with her in her performance at the VMAs. I wore this red beaded dress and leather jacket with an older woman’s face makeup and played Miley’s sidekick. The director made sure I was right next to Miley the whole time. I really got to know her. She would come on the set for the rehearsals and say, “Where’s my Gypsy?” We would joke and I’d say, “I know why you always ask for me — you want to see if I lived through the night!” Even if I wasn’t in a certain take, she would want me to stick around and watch her. I got something that very few people get with these superstars: a true look at what she’s like as a human being. Also, she doesn’t lip sync! She has a very interesting, rich voice, not quite like anyone else’s.

The only serious thing about me is my clothes

For the last several years, I’ve been headlining shows. When I was 68, my current manager and producer, Dan Gore, asked me to headline a show in Lake Tahoe, and I said yes. He asked, “Do you have gowns?” I said, “I have 200.” We became the longest-running show in history there. Then we came to Palm Springs and opened various shows. The last four years, we’ve been at Oscar’s Café & Bar.

The only serious thing about me is my clothes. Every time I come out onstage in a new dress, the crowd doesn’t applaud me; they applaud the gown. When audiences see me, it’s always, “Gypsy, that outfit!” not “Gypsy, god, you look just like an old lady.” It releases me to be myself in a dress. I never lose myself when I’m in costume — I’m always myself, in costume or not. I am who I am.

The Guinness Book of World Records named me the world’s oldest … they called me “impersonator,” but I’m not really. I don’t impersonate celebrities — I’m my own persona dressed up in these costumes. I never put on the costumes or makeup during the daytime unless it’s for a photo shoot or special performance. If you saw me out of context, it wouldn’t really make sense.

Dan, besides being my producer, is also my family. I live in his condo with a dog we got from the shelter. Very few people at 86 have people who care enough for them to help them to keep working, especially in this business. I want to keep working as long as I can. I had an artificial heart valve surgery two years ago, but I’m perfectly fine. I’m always prepared to do whatever I need to do.

Photos by Maggie Shannon.

Jackie Homan

Jackie Homan

Jackie Homan is a journalist, writer, and proud owner of an indoor s’mores maker for the rainy days.

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