Maude Maggart is the voice of a generation, even if the generation isn't hers. At the Algonquin Hotel's Oak Room last month, in her New York solo cabaret debut, she wore a pink beaded gown with a scarf draped over her elegant neck, and the chatter of the crowd hushed as she began to sing. Maggart has a sound that swells out of the past: a sweet, unadorned soprano with a fast vibrato that floats straight from the memory of such great 1920s torch singers as Helen Morgan and Libby Holman. If you close your eyes, you can almost hear the crackle of a Victrola. Not every cabaret starlet launches her career at the Oak Room, the venerable spot where Dorothy Parker and her vicious circle once lunched, and that now features some of the top cabaret talent in the world (Harry Connick Jr. and Diana Krall both got their start there)

But Maggart, 28, is no ordinary singer. The scion of a musical family-her sister is the pop singer-songwriter Fiona Apple-Maggart has been championed by two of cabaret's biggest stars: the sharp chanteuse Andrea Marcovicci and the renowned pianist and singer Michael Feinstein. "Maude is wise beyond her years," says Feinstein, who introduced Maggart to the city's cabaret scene in his 2001 Christmas concert. "She has a great connection with everything she sings, which is something that you can't teach." On Monday 8, Maggart kicks off a weekly engagement at Danny's Skylight Room, performing songs made famous 50 years before she was born.

To hear Feinstein and Marcovicci talk about her, you get a clear impression that the torch song is being passed. Poised and lovely, Maggart comes from a line of show-business troupers. Her grandmother debuted on Broadway at the age of 15 in the Ziegfeld Follies-esque George White's Scandals of 1926; her parents, Brandon Maggart and Diane McAfee, are Broadway veterans who met while performing in the 1970 musical Applause (Fiona Apple uses her middle name professionally). Maggart stayed in New York with her mother after her parents' separation and trained in music and dance at the La Guardia High School for performing arts, better known as the Fame school. ("Nobody danced or sang on the tables," she says with a sigh. "Not even at lunchtime.")But she spent summers with her father in California, where she met the Broadway lyricist Marshall Barer (Once Upon a Mattress). "Marshall would throw these crazy parties every Sunday at his house in Venice-he called them his Sunday soirees," Maggart recalls. "People would gather around his white piano and perform. My sister sang the first songs that she wrote there."

Marcovicci and Feinstein were sometime guests at these evenings, and Barer eventually cast Maggart opposite Feinstein in a Los Angeles staging of his musical A Happy Lot. Later, while singing at Barer's 1998 funeral, the young singer caught Marcovicci's ear. "This child was up there singing like an angel-a piercingly haunting angel," Marcovicci says. She contacted Maggart immediately and offered to help hone her act. Maggart was thrilled at the prospect, having idolized Marcovicci for years. "I saw Andrea at the Gardenia in Hollywood for the first time when I was 16 or 17, and I rushed home and wrote pages and pages in my diary about how special it was," she recalls. "She was like a spell caster. It was the experience of appreciating a song for its craft: how it was constructed and how it could best be expressed." When Marcovicci reached out to her, Maggart says, she already knew that she was interested in a career in the arts, but was unsure whether to pursue music or dance. At Marcovicci's urging, she put aside her other interests and "just fell into cabaret." It was Marcovicci who first suggested that Maggart's voice was ideally suited to the songs of the 1920s.

"Maude has a voice we haven't heard in 60 years," she says. And as Maggart immersed herself in the old songbooks, she discovered the classic melodies and witty double entendres of a bygone era. "Some of the greatest songwriters were writing then: Cole Porter, Hoagy Carmichael, George Gershwin, Rodgers and Hart," Maggart says. "I sing the songs basically the way they were written, because they are perfect. They're simple and complex at the same time." But Maggart faces an uphill climb if she is to achieve success anything like her sister's. Cabaret is not lucrative and is largely ignored by the mainstream music press; most of the attention it does draw is reserved for established international performers or theater stars. What's more, performances can be daunting, especially for a singer still finding her bearings. "Cabaret is brutally honest in its parameters," Feinstein says. "It is vérité; the intimate exposure to the audience strips a performer to his or her essence." Maggart adds, "If you're being truthful, it comes off-and if you're faking it, that comes off too. I have a friend who used to say that he wouldn't go to a concert unless he could see the person's eyelashes. In cabaret, you can pretty much see my eyelashes wherever you are."

Maggart plans to cultivate the ambience of a Prohibition-era speakeasy in her weekly show at Danny's-"When the show is done, I can play hostess, like Helen Morgan did when she ran her own club"-and hopes to attract a crowd that may not know much about cabaret, but would embrace it as part of the lost art of sophisticated dating. "The songs are still applicable to romance," she maintains. "It's an experience of another time-like when you come across an old book or movie and get lost in that world."

In time, Maggart's enthusiasts expect her to develop a loyal following that will appreciate her unique talents. "It's strange to say, because she's my older sister, but I feel so proud of her," Apple boasts. "She has taken a raw, pure love of something and made it beautiful. And she's got this fucking charisma-you just want to keep on looking at her. She's a sight to see."

Maggart has not yet decided where the future might lead her, or even if she will stay in cabaret. But for now, she's delighted to be right where she is. "You get to dress up and look pretty every night, you sing your favorite songs for an hour, you make people laugh and move them-and that's your job!" she says. "And hopefully, you break even, you know?"