Alexandra Grey's True Hollywood Story Is Breaking Barriers

Alexandra Grey was the only eighth-grader in her middle school's production of the musical Once on This Island. Though everyone else in the cast was in sixth grade or below, it didn't matter. The young actress knew she had found her passion.

Grey's life has been an uphill journey toward stardom ever since, but it hasn't always been easy. After the traumatic experience of being disowned by her foster parents and a stint experiencing homelessness, she made a courageous decision to leave the South Side of Chicago and pursue her destiny in Los Angeles. Grey arrived with nothing but $30 and a dream, but now she's finally getting the credit she deserves.

In the last few years, Grey has earned critical acclaim on shows like Code Black, Chicago Med, The Alienist, How to Get Away With Murder, Transparent, and Drunk History (as Marsha P. Johnson), the last two earning her well-deserved Emmy buzz. Roles in Lee Daniels's Empire and HBO Max's Equal, as legendary trans socialite and chef Lucy Hicks Anderson, have further secured her place as one of Hollywood's biggest on the rise stars.

Still, when she was growing up in Chicago, Hollywood felt light-years away. "I didn't have the language for it, but I always knew that I liked being the life of the party and being outgoing and making people laugh," she says.

Dress by Genny. Heels Vince Camuto.

It wasn't until a coworker encouraged Grey to move to L.A. and become an actress that she even considered it a possibility. At the time, she had just graduated from community college and had been kicked out of her foster home.

"I was like, what do I have to lose?" she remembers. "So I just said I'm going to go to L.A. and I'm going to be an actress." Six months later, she was in Hollywood on her first movie set.

Of course, being in the right place at the right time is nothing new for Grey. No matter how challenging the dream might be, when she decides she wants something, she goes for it. Her star power was evident as we chatted during a Zoom call in early January. Grey's smile lights up a room. She's funny, sweet, and speaks with such conviction that it's almost impossible not to hang on every word.

"I said, 'God, if it's your will for me to go here and make it, I'll do it,'" she remembers of her flight to L.A. "It was the emptiest plane I have ever been on. There were maybe seven or eight of us. I had this whole row to myself and I was in tears the whole time, thinking, What am I doing?"

Grey's fear was short-lived. Submitting numerous applications for background work in TV and film to make ends meet financially as well as get her foot in the door paid off.

"I remember getting to the shelter that night. I checked my email -- I had a little tablet -- it said, 'Congratulations, you've been cast as a background character in this feature film, and it's going to shoot in three days,'" she recalls.

Turns out, she was one of three extras chosen to audition for a small speaking role. Though she didn't get that role, it ended up being a clear sign she was on the right track. "So I was on a set my second day in L.A. while I was in a shelter," she says. "I just remember feeling like, Oh my gosh, I asked God on that plane to give me a sign that this is what I'm supposed to do. And he gave me that sign."

Grey spent the next five years grinding, living in and out of shelters, working everyday jobs, and taking any acting role she could, no matter how small. Then in 2015, the opportunities began to grow.

Full Look is Maxrieny by Sara. Shoes by Giuseppe.

That year, Grey, also a singer, made it to the executive producer round of American Idol before she was turned away. She also auditioned for the lead in Lee Daniels's Star, a role that ultimately went to Amiyah Scott. But Daniels was so floored by her audition that he promised to cast her in a future role -- and he did.

"I was like, wow, that's another sign for me," she says. "Look how close you came to getting on American Idol. Look how close you came to working on a Lee Daniels show. Keep going!"

Less than a month later, Grey booked her first big guest star role -- as Elizah Parks in Transparent. "I was determined after hearing Lee Daniels's [promise]. I was determined to never hear 'no' again."

Daniels went on to hire Grey to work on six episodes of his monster-hit Empire as trans singer Melody Barnes. The actress still gets emotional speaking about the role. "A lot of people don't value the Black trans story," she explains. "I really love that they honor that she was an artist and she was a singer and that they trusted me to take on such a big role."

Her character was so beloved by fans that she instantly started trending on Twitter. It was a vindicating moment not just for Grey but for other Black trans actors.

"We're bankable and we're marketable, baby. People don't care that we're trans. They want to see good acting. They want to see good writing," she says. "I've played a superstar. I've played a murderer. I just played a rock and roll person. The sky's the limit."

Despite the passion, Hollywood, it seems, takes a while to catch up. In recent years, the entertainment industry has been criticized for continuing to cast cis people in trans roles. But according to Grey, many critics are missing important points in the discussion.

"We don't even get invited to play the roles, and sure, we don't want men dressing up as a woman playing our roles. If you want to cast somebody, cast a cis woman, because at the end of the day, it's still a woman," she explains. "I don't think it's that we're trying to police it and say, 'You can't do this.' It's like, no, there are many capable actors out here." And those actors deserve a shot too.

Dress by Monte The Label. Jewelry by David Yurman.

Make no mistake; Grey is keenly aware of the role she plays in blazing a trail, placing her alongside other trailblazers like Dorothy Dandridge, one of Grey's role models and the first Black actress nominated for a Best Actress Oscar. She's also aware that more trails have yet to be cleared.

"I think the fact that there's only been one Black actress to win Best Actress after what -- 60 or 70 years at this point? It's a shame," she says. "[Dandridge] made it easier for Black girls and it may take another 20 years for us to get to the point where it's just a part of the norm for trans people to exist on television and to win Emmys and Oscars."

As for the future, Grey is continuing to follow the signs. Expressing her desire to work with such greats like Lena Waithe and Justin Simien as well as mainstream directors like James Cameron and Steven Spielberg, above all she yearns to tell stories that are uniquely about Black trans women, including those from history.

"Any chance I get to pay homage to the people that have come before me and have lived so that I could live and stand and be as proud as I am today, I always jump at that opportunity," she says. "It's important for Black trans women to see themselves, and I want people to know that, hey baby, they're telling our stories. So I don't want fame. I don't want any of that. I want to be a light because I know the impact it has."

She continues, "Imagine if there were 15 Laverne Coxes or 15 Candis Caynes. I think that allows trans people and trans women of color to see themselves and say, 'Wow, I can do anything, because look... she did it.'"

On Jake & Ryan: full look and accessories by Louis Vuitton, shoes by Giuseppe. On Alexandra: dress by Annakiki, jewelry by David Yurman.

This feature is part of a three-part cover story of Out's 2021 Hollywood Issue. Alexandra Grey is featured on the cover alongside Ryan O'Connell and Jake Borelli. It is the first print issue under the editorial direction of editor-in-chief David Artavia. The issue is out on newsstands on March 3, 2021. To get your own copy directly, support queer media and subscribe -- or download yours for Amazon, Kindle, Nook, or Apple News +.

Photography by Easton Schirra, assisted by Danya Morrison.

Styled by Aisha Rae with assistants Angel Cross and Tashie Pollard. Makeup by Dillan Pena. Alexandra's hair by Lisa-Marie Powell. Jake and Ryan's grooming by Sonia Lee.

Art Direction by Ben Ward. Shot on location in Boyle Heights. Special thank you to Jake Noonan.