From single motherhood to the college admissions scandal, at 50, she's done holding back. 

Debra Messing
Credit: Tina Turnbow

The last time I spoke with Debra Messing, we were standing in the living room of a Brentwood home kitted to the nines with free goodies, and she was espousing the benefits of celery juice. She was also three days away from turning 50. So when we reconnect five months later, on the day of the Will and Grace reboot’s second season finale, I ask how the landmark year’s been treating her.

“Fifty feels fantastic. Wow, that could be on a T-shirt, couldn’t it?” she says, laughing, before leveling. “Forty was not the greatest. I just assumed that 50 would be more challenging.”

Messing became a household name in 1998, when she brought the spirited and expressive Grace Adler, on NBC’s Will and Grace, into living rooms across the country. When the network decided to do a reboot in 2017, it was only slated for 10 episodes. Neither Messing nor her castmates, she says, had any idea whether there’d be an appetite for the show now. But the ratings are in; its original fans were ravenous, as Messing says many stop to tell her.

“There’s a sense of gratitude for this show because things in our country are so divisive, confusing, and scary. People say that at least they know on Thursday night there’s a half-hour where they can predictably sit down and know that they’re going to laugh out loud. And it really feels like a gift to us to be able to provide that,” Messing says. This go-around, she had one request for producers: make Grace a feminist, like she is. And they did. She’ll shoot season 3 this summer.

If Messing’s trademark physical feature is her cascading red curls, her signature emotional quality is her forthrightness, as she’s among the rarest of Hollywood creatures: a good interview. She's quick with her truth, which has both cultivated an enduring bond with her fans and opened her up to criticism.

Messing has publicly gone up against the New York Times, Susan Sarandon, Megyn Kelly, and Donald Trump, among others. And once she’s in the ring, she rarely drops a fight; when Sarandon demurred after Messing fired shots on Twitter, she continued to twist the knife on Instagram; when Messing was angered by the Times’ coverage of white supremacists, she tweeted that she’d canceled her subscription, then tweeted it again three days later, just to ensure they got the message.

“It would just really go against my nature to have this platform and to just sort of sit back and ignore it,” Messing says. “I don't pretend to have any expertise. I don't report to have a more important voice than anybody else in the world. I just recognize that I have a louder voice than many.”

In using that voice, she has occasionally — and inadvertently — offended those she sought to support, as when she posted a selfie in support of gun control that some perceived as tone-deaf or shared an image of vagina-decorated cupcakes that some criticized for being trans-exclusionary. In both instances, Messing apologized immediately. Calling herself “heartbroken and embarrassed” by how her gun violence message had come across, she tweeted an apologetic note. Upon hearing the response to her International Women’s Day photo, she updated the Instagram caption. Messing tells me she is “a perpetual student.”

As a single mother to 14-year-old Roman, Messing says education is “the most important gift we can give our child,” and her parenting philosophy is to support him growing into whomever he will become. She bristles at the fact that some of her peers seem to have different values here. On the topic of the college admissions scandal, she says it “shines a light on this idea that name recognition, when you're talking about college, is considered so valuable that people will go to extreme lengths to secure that status symbol,” she says. “That people would cheat and spend hundreds of thousands of dollars to secure that tells us that there is something very, very wrong with our educational system.” Not every child will excel in the same way, Messing says.

“These kids are great for who they are; whoever they are, whatever grades they get, if they’re in school and they’re working hard and they’re doing their best, then their best is good enough. I want to celebrate people trying their hardest, whatever that result is. If the result is getting all Cs, then that’s worth celebrating. Whatever school is appropriate for them, that’s worth celebrating.”

Nowhere is the human impulse to compare status more heightened than on social media, of which Messing, the mom, is acutely wary. “The thing that makes me feel the most out of control and anxious is the interaction on social media. It wasn’t too long ago that there were no smartphones; you had to use a telephone or communicate on the computer,” Messing says. “You didn’t have the ability to go into your room, close the door, and communicate with complete strangers.” She calls using these platforms “a continual conversation” between herself and Roman, whom she has allowed to have an Instagram account, so long as it remains private. “The challenging thing at this stage is to support his autonomy, encourage his independence, and respect that he has a voice, but still do my job as a parent to protect him and give him boundaries.”

Debra Messing
Credit: Tina Turnbow

Equipment Jacket; Muzo Earrings.

Tina Turnbow

It’s not all austerity in the Messing household, to be sure. She reportedly commands a quarter million dollars per 22-minute episode of Will and Grace. She lives in an Art Deco-style apartment overlooking Central Park, though it was severely damaged by smoke from a nearby fire right before the reboot filmed, which sent her scrambling into temporary housing. Her jewelry collection is the stuff of legend — in 2017, the Jewelers of America honored her with an award for it — but she says her one desert-island item, without hesitation, would be her mother’s 50th wedding anniversary band. “She passed suddenly, so that’s an incredibly special and meaningful piece to me,” Messing says.

Few of these investments appear on her social feeds, though, which Messing, the professional, says fulfill a primarily tactical function. “Posting on Instagram and Twitter is literally part of my job; letting people know that the season finale is tonight, and posting pictures from it,” she says. (Followers will also find behind-the-scenes snaps, a little Roman birthday love, a puppy here and there, and advocacy information about the many causes she supports.)

Strategic though she may be, Messing is far from a calculated caricature — she's a real-deal actress with her theatrical bona fides in order. She shot out of the cannon in a burst of glitter, starring in Annie and Grease at her Rhode Island high school; winning the state’s Junior Miss competition, where she put her singing, dancing, and acting lessons to work; and playing Harper Pitt in Perestroika, the second part of Tony Kushner’s Angels in America, in its legendary first staging at NYU, where she was a graduate student in Tish’s tiny and near-impossible-to-crack program.

In the intervening years, she’s become known for her full-throated physical comedy; “I’ve sprained my back and neck too many times to remember,” she told the New York Times. But she’s also received critical praise for her dramatic roles, including in John Patrick Shanley’s Outside Mullingar, which received a Best Play Tony nomination in 2014. “The thing that makes theater special is that it is finite. It exists in the moment, in real time, with 1500 people and then that's it,” Messing says, quickly flipping to the other side of the coin. “In my heart, I wish that more people would have been able to see that production, because I really loved it.” This sentiment is true to her astrological identity; Leos are known by their desire to share their work and life with the world.

“I am the quintessential Leo,” she says. “I have a big mane of hair, I like to entertain, I’m social, and I’m very connected to the idea of justice.”

For Messing, justice means throwing her weight behind liberal candidates and policies, supporting the marginalized, and working on women’s issues. She’s testified before Congress about the need for increased HIV prevention funding and treatment in African countries; and has worked with with Population Services International (PSI), a development-focused non-profit garnering support for public health projects in Zimbabwe, Zambia, and Malawi, for more than 10 years. Recently, she joined a campaign against the anti-abortion bill in Georgia, which she calls “extreme” and “very scary,” and which has since been signed into law.

“I am just trying to follow the examples of people who have been trying to equal the playing field for decades,” she says of her advocacy work. To that end, she spoke at the 2016 Democratic National Convention and at the 2017 GLAAD awards, where she received the organization’s Excellence in Media award. She was the first to put E! News on public blast over pay equity on the 2018 Golden Globes Red Carpet. “No one does that!” designer Christian Siriano told Vanity Fair. “It was insane! It was so beautiful to watch.” During a Hollywood Reporter roundtable, she was asked if she had feared the ensuing fallout. “No,” she answered, succinctly.

After years in the public eye, Messing manages to be both steadfast and surprising. She’s unafraid to share her experiences, unafraid to stand firm when convicted, and unafraid to learn from her mistakes. At 50, Messing says, “I feel really clear about who I am.”

Makeup by Gita Bass/The Wall Group. Hair by Peter Butler/Tracey Mattingly. Special thanks to The Standard, East Village.