Messing Up Stereotypes

When Debra Messing heard she’d been cast as Woody Allen’s girlfriend in his new romantic romp, “Hollywood Ending,” she shrieked.

“I was in my car, and I almost caused an accident,” gushes the spunky, green-eyed redhead, best known as the kooky Jewish gal pal to a gay lawyer on NBC’s “Will & Grace.” “I come from a Jewish family from New York, so Woody Allen is almost mythological to me. To star in one of his movies — I was over the moon.”

Messing plays Lori, a ditzy tart of an actress dating a washed-up director (Allen) with one last shot at success. Never mind that the pairing is, well, ironic: Allen’s known for depicting not-so-nice Jewish women (think the nagging mom from “New York Stories”), while Messing’s overturned every Jewish female stereotype on television. Forget pathetic Melissa from “thirtysomething” and obnoxious Vicki from “Suddenly Susan.” The fictional Grace Adler is a hip, gorgeous, lovably klutzy interior designer with way-cool clothes and an unabashedly Jewish sensibility. The character spouts Yiddishisms, reminisces about Camp Ramah, confesses to eating a burger on Yom Kippur and describes her excitement at being profiled in the Jewish Forward. When Grace breaks up with her latest inappropriate beau, she chants, “Baruch Atah Adonai, I’m gonna die alone.”

You could call her the anti-Seinfeld: “I remember thinking Jerry’s friend Elaine was Jewish, then learning she wasn’t,” the Emmy-nominated Messing, 33, told The Journal. “Then I thought, Seinfeld’s friend George must be Jewish, but his last name was ‘Costanza.’ It’s like the sensibility was Jewish but the characters weren’t. Which is why I encouraged the ‘Will & Grace’ writers to include more Jewish references for my character. I thought it would be great if Grace were open and unapologetic about being Jewish; if her Jewishness were just a fact, the way it’s a fact that Will is gay. I thought it would be neat and an inside joke for my family if we could have smart jokes that revealed Grace’s Jewishness, while at the same time making her endearing to the audience.”

“Will & Grace” co-creator Max Mutchnick, agrees: “Grace doesn’t fall into any of those categories that have stereotyped Jewish women,” he told The Journal in a 2001 interview. “She’s strong, she’s pretty and she’s a proud Jewish woman.”

If Messing projects a certain vulnerability as Grace, it’s because she’s had some practice. “I never felt beautiful growing up,” confides the 5-foot-8 actress, who was born in Brooklyn but raised in rural Rhode Island. “I didn’t think my big hair was attractive. It took me a long time to come to terms with my looks.”

It didn’t help that Messing — the daughter of a jewelry executive active in the Rhode Island Jewish Federation — was one of only a few Jews at school. When she was in the third grade, a boy pushed her and called her a “kike” (around the same time, a swastika was painted on her grandfather’s car). “I felt the desire to lie and say I was sick on Yom Kippur, because kids got mad and thought it was unfair I got the Jewish holidays off and Christmas, too,” Messing recalls. “I did feel different being Jewish. I felt like an outcast throughout elementary school.”

She escaped into the Jewish milieu of Woody Allen’s films, which were de rigueur in her childhood home. Messing also nursed a wicked crush on actor Dustin Hoffman, became a bat mitzvah at a Reform temple and trekked to Brooklyn to visit her Jewish relatives. During one such visit, her mother, Sandy, a onetime professional singer, took her to see “Annie” on Broadway. Messing, then 7 years old, leaped out of her seat and declared, “I’m going to be Annie one day.” By the age of 16, she was playing the role in a high school production, though her parents insisted she attend college before drama school.

So Messing was off to Brandeis University, where she says the heavily Jewish population proved “shocking but, ultimately, a relief. It was amazing to not feel ashamed, to not have to make excuses for my holidays and to meet people who’d had similar family experiences.”

After graduating summa cum laude from Brandeis, Messing earned a master’s degree in theater from New York University and became the quintessential struggling actress — until her father revealed he’d invested her bat mitzvah money and parlayed it into $30,000. The funds helped sustain her until she began landing roles such as a scheming sister on “NYPD Blue” and Jerry’s elusive ideal girlfriend on “Seinfeld.”

In 1995, Messing snagged the lead in the Fox series, “Ned and Stacey,” though she bombed her initial audition. “They said I was too wholesome,” she recalls, with a groan. “They wanted a neurotic Jew from New York, and I said, ‘Hello, I’m right here.'”

If Stacey was Jewish in name only, Grace Adler is anything but. While “Will & Grace” broke ground in 1998 as one of the first network series to feature an appealing gay main character, it was a first for another reason: “There [hasn’t] been a more positive role model for Jewish women on television in the past 50 years,” as the Forward put it.

Messing, oddly, expresses surprise when told about the Jewish community accolades. “No one’s articulated that to me, but I consider it a huge honor and a privilege,” she says. “I had hoped Grace would be to Jewish people what Will is to gay people.”

While Grace has never seriously dated a Jewish man, Messing wed Daniel Zelman, an actor-screenwriter, in a ceremony conducted by a rabbi in September 2000. The couple attended High Holy Day services in Los Angeles last year (they live in the Hollywood Hills), though Messing describes her Jewish identity as “more cultural than institutionalized.” She performs her share of tzedakah by supporting charities such as the Gay Men’s Health Crisis and Best Friend’s Pet Sanctuary.

Another Messing contribution to the Jewish zeitgeist: “Will & Grace” director James Burrows calls her “Juicy,” the Jewish Lucy, because of her prowess for physical comedy. Anyone who remembers the exploding water-bra episode understands why critics agree she’s a sexier, contemporary incarnation of Lucille Ball. Even Allen noted Messing’s comic ability and cast her in a cameo in his 1998 film, “Celebrity.”

The audition, she recalls, was unorthodox: Before asking her to read, she says, “Woody stared at me for 30 seconds, and I stared back.”

Starring in “Hollywood Ending” also proved daunting. “Woody doesn’t give you the entire script, which is the actors’ bible, so that’s very disarming,” Messing says. “Then he sort of leaves you alone for a long time and doesn’t say anything and just lets you find your way. Often you don’t rehearse and you get only one take; it’s so fast it makes your head spin.”

Messing’s career trajectory has been equally head-spinning. She’s appeared on every magazine cover from Cosmo to Glamour and recently flexed her dramatic muscles by portraying Richard Gere’s doomed wife in the “The Mothman Prophesies.” She says her goal is “to work within all mediums and to switch genres as often as possible.”

Playing the very un-Grace-like Lori in “Hollywood Ending” has helped. “It’s been an amazing experience,” she says. “To star in a Woody Allen movie — as his girlfriend, no less — has been a real-life Hollywood ending for me.”

The film opens today in Los Angeles and May 15 at the Cannes Film Festival.