Diva Friday: Alexandra Billings

As I lay languishing for a leading lady to lavish with my literary laudations (don’t mind me, it’s been a long week), I got the following text from my friend Sarah:

“Guess who’s Grand Marshal of the Pride Parade on Sunday? Alexandra Billings!”

And so that was it. This Diva Friday, let’s rejoice the singular sensation that is Alexandra Billings.


I became acquainted with Miss Billings about nine years ago, when Sarah, our good college friend Bernadette (not Peters! But my, how fun that would’ve been!) and I took a very impromptu trip from Albion, MI to Chicago. I had a sudden urge to see a show in the Big City, and Google directed me to a production of Gypsy at some place called The Bailiwick.

Having been a long-time fan of the musical Gypsy, I was excited to see a professional production. The four-hour drive to Chicago was a blast, and we made it with just a few hours before curtain. I went to the box office to collect my ticket, and on a table next to the box office window was a magazine spread about the star of Gypsy: Miss Alexandra Billings.

As I scanned the article while waiting for the box office guy, I read the following:

“Alexandra Billings is the premier, Chicago-based transgender performer of our time, and she is now starring as Mama Rose in Bailiwick Repertory Theatre’s production of Gypsy.”

Wow! This was gonna be SOMETHING! Still a small town boy, I ran out and told Bernadette and Sarah what I had learned. Wow! Our first transgender female, live – up close! And in a show I adore!

Well, it was a very basic production, with a piano, bass and drums. Very store-front theatre. But Miss Billings was dynamite. What a voice! And what star power! It’s a performance that stuck with me for some time.

When I got home, I did my research on Miss Billings, learning all about her powerfully dramatic story and bought her CD: Being Alive. Bernadette, who was a foreign exchange student from Austria, was equally amazed — even doing a speech on Miss Billings for a class later that year.

Sadly, for whatever lame reason, I haven’t seen her perform live, since. And she’s currently living in Hollywood with her partner of nearly 30 years.

She’s not only a stunning performer, but also a staunch character, as was the focus of her recent WTTW documentary: Schoolboy to Showgirl: The Alexandra Billings Story (Which I also missed…the hell??)

I’ll be there cheering her on come Sunday!

For more information on Alexandra, visit her web site.

To close us out, Miss Billings in her element. Take it, Alexandra!

(Special bonus! Katie’s Corner!):

(Special *special* bonus! Alexandra vlogs on her way to an audition for a CBS pilot. Side note: This is pretty much me when I drive to work. It’s like a cast of characters in my Subaru!)

Visit previous Diva Friday columns.

One thought on “Diva Friday: Alexandra Billings

  1. Thanks you writing about my client and longtime friend Alexandra. I have been her producer since the early nineties. Gyspy was aspecial project that I co-produced, it was a joy. The CDs “Being Aleve” and the followup “The Story Goes On” are still selling. If you wish to see Alex perform while she’s in Chicago this summer, I am producing a benefit for Bailiwick Theater on July 26th at 8pm. Alex is appearing in it as well as Alanda Coon, Jeremy Rill and others. You can google and get the information – it’s at the Center on Halsted. Thanks again!
    Lampkin Music Group

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