Cabaret singer Maude Maggart comes from a family steeped in the world of professional entertainment. Her maternal grandmother, Millicent Green, appeared in George White's Scandals of 1926 and met Maggart's grandfather, Johnny McAfee, when she successfully auditioned to become the girl singer in the Johnny Hamp Band in 1937; McAfee was a reed player in the band and, after they were married, he moved on to the Harry James Orchestra. Maggart's parents, Brandon Maggart and Diane McAfee, were Broadway performers who met when they were both cast in the 1970 musical Applause. Her younger sister is pop singer/songwriter Fiona Apple. She was born in Manhattan and raised in Los Angeles until the age of seven, when her parents separated and she moved with her mother and sister back to New York. There, she attended La Guardia High School of Performing Arts (the high school immortalized in Fame). She was living with her father in Los Angeles in 2000 when she began performing at open-mike nights, notably at the Gardenia in West Hollywood.
Initially mentored by Andrea Marcovicci, Maggart was introduced to New York's club scene by Michael Feinstein, who had her make a guest appearance on his Christmas show in 2001; she made her formal nightclub debut at Danny's Skylight Room in Manhattan in 2003 with a program devoted to songs of the 1920s. It formed the basis for her self-released debut album, Look for the Silver Lining, just as her next show, The Talk of the Town: The Music of 1933, inspired her second album, With Sweet Despair, in 2004. By then, she was appearing at the prestigious Oak Room of the Algonquin Hotel in New York. Along with other stints at such clubs as Feinstein's at the Regency in New York, the Plush Room in San Francisco, the Colony Hotel in Palm Beach, the Savor Room in St. Louis, and Schroeder's in San Diego, this helped her win the MAC Award for Best Female Debut in 2005, and the same year she earned awards for special achievement from Time Out New York and Back Stage magazines. Her third album was Maude Maggart Sings Irving Berlin, reflecting the evening of Berlin's early songs she was performing in 2005. On March 13, 2007, she released Live, a CD culled from shows at the Gardenia and the Oak Room, and based on the 2006 version of her nightclub act, which she called Comes Love and dedicated to her grandparents. Meanwhile, she had already premiered a new version of her act, dubbed Good Girl/Bad Girl.