Known for her brassy style, and big Broadway belt, O'Shaughnessy's three-decade career began informally as a child. She and her family would gather around the piano after Sunday dinners while her grandfather played and sang all the standards of the day. "I had a childhood so good that I was embarrassed by it," she muses. "I had a very functional and supportive family." Up until a point.
While O'Shaughnessy used to delight her neighborhood with backyard shows that were something right out of a Hardy Boys film, her mother had a more practical career in mind for her daughter. In spite of O'Shaughnessy's success as a performer in Gilbert and Sullivan operettas at Arlington High School, her mother persuaded the Arlington High School thespian to drop acting for a career as a medical secretary. Soon after, O'Shaughnessy got married and started a family. It would be eight years before she would perform again professionally.
Marital conflicts and the urge to perform sent O'Shaughnessy searching for her high school drama teacher, Ludvio Einsick, who had founded the Winchester Staff and Key Society, devoted to performing Gilbert and Sullivan. "I was five-months pregnant with my third child, and still I went to audition for him -- and I got the job. At seven months pregnant I was performing in the chorus of H.M.S. Pinafore." But it was in The Yeoman of the Guard in 1968 that she got her first real break: Egged on by a colleague to audition for a principal role, O'Shaughnessy nailed the part of Dame Caruthers. She recalls, "This encouraged me to take voice lessons, which then opened up a huge field of music for me."
Armed with a growing repertoire, O'Shaughnessy played wherever she could, from weddings and bar mitzvahs to coffeehouses and senior living centers. "My mantra was 'work everywhere, work everywhere, work everywhere,'" she quips. On a date in the early '70s, O'Shaughnessy disclosed her career ambition to be a singing waitress. And it was in 1978 that she landed her dream job at Romie's in Danvers. After failing to land a job there a few years earlier, a determined O'Shaughnessy put everything she had into the second audition, producing a belt that she never knew she had. Romie's turned out to be everything she was looking for in a job. "We worked our tails off, three shows a night, five days a week, but it was the best place to learn your patter, and how to improvise on the spot."
During her time at Romie's her gay male colleagues couldn't help noticing O'Shaughnessy's vocal resemblance to another famous belter with heart: Judy Garland. They turned her on to Garland's Live at Carnegie Hall recording, and that clinched it for her. "My mother told me that Garland was the best singer because she [understands] the lyrics," O'Shaughnessy remembers. Her biggest supporter at Romie's was her colleague and friend Richard Collins, who finally persuaded O'Shaughnessy to get up and sing a song during his own cabaret act at a gay club in Worcester called The Male Box. Knocking out a Garlandesque "Rock-a-bye My Baby," O'Shaughnessy was offered a string of gigs right then and there.