Debra Messing: No Fear of Failure

For Debra Messing, winning and losing are both valuable tools for learning. With a new home, a new boyfriend and new career choices, the star of Smash and Will Grace talks about taking risks and learning to love “the gift of change”

by Leah Rozen
debra messing image
Black Fleece by Brooks Brothers tuxedo shirt and silk tie; brooksbrothers .com. Ralph Lauren Collection suede heels; Martin Katz 18k gold ring with white and yellow diamonds;
Photograph: Ari Michelson

Smash kicked off to enthusiastic reviews and solid ratings. Critics and fans, however, soon grew disenchanted with the personal melodrama of its story lines, including one in which the married Julia beds an actor played by Will Chase, whom Messing is now dating in real life. For its second season, both Smash and Messing’s character received makeovers—Julia’s husband, son and unflattering scarves all went -missing—but the reboot didn’t take. Ratings sank perilously low, and at the time of our lunch, a cancellation appeared all but certain. It is a prospect that fills Messing with sadness. “I loved Smash,” she says. “It made me happy to return to the world that first mesmerized me as a child: the lights and glamour of Broadway musicals.”

She remembers being five or six and, despite her fear of the garter snakes lurking in a swamp below, crossing a wobbly wooden-plank bridge to get to an island behind their house. Her father had dubbed it Gilligan’s Island, after the ’60s sitcom. “I honestly think I made it over because I wanted to be Ginger so badly,” she says, recalling the movie star among that show’s shipwrecked characters.

Messing was born in Brooklyn but moved at age three with her parents and older brother to East Greenwich, a small coastal town in Rhode Island. She first ventured onstage at age eight, portraying a blind girl in a play at summer camp: “I wanted to know what it was like to feel blind, so I rehearsed with my eyes closed—and fell into the orchestra pit.” Undeterred, she became a regular in school theatricals, adopted Fame(1980) as her how-to guide and set her sights on a stage career. “It’s the cliché: I didn’t feel entirely accepted as myself, and taking on another character, I felt completely free to be bold, eccentric and assertive,” she says.

She also competed in beauty pageants, winning the Miss Pre-Teen Rhode Island title, though her tiara was tarnished when classmates dubbed her Miss Latrine. As a senior, she entered the Junior Miss contest and won at the state level but failed to become a finalist in the national competition: “I learned that disappointment was a necessary part of the path I was taking.”

Geography dictated her college choice. After being rejected by her brother’s alma mater, Brown University, in nearby Providence, she opted for Brandeis in Waltham, Massachusetts, because it had an excellent theater program and “was close to home,” she says. “I was not brave enough to go very far.” She thrived in its competitive atmosphere (“You’d go to the library to get reference material, and it would be ripped out of the book so the next person couldn’t get it!”), graduated summa cum laude and then won a coveted spot in the graduate acting program at New York University. She loved the program, especially its emphasis on tackling roles that seemed an unlikely fit. “It was all about taking big risks and learning how to embrace failing big because the only way you were going to get better was by failing,” she says.

After getting her degree in 1993, Messing quickly landed a plum part in a production of The Importance of Being Earnest at a well-regarded theater in Seattle. But to her dismay, she soon realized she was a confirmed homebody: “I’m in this great theater in this great part, and I find myself profoundly homesick. I’m not a gypsy.”

First published in the June 2013 issue

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