Jenny Pacquette was raised in a musical family. Her grandfather and two uncles were involved in country music, while her father performed in a popular '70s rock band. As a teenager, she briefly considered studying classical music and was accepted at the Boston Conservatory of Music, but decided before enrolling that her future lie closer to her musical roots. She began performing powerful, rock-inflected contemporary country music, and received her first big break in 1998 when she won the state and regional competitions for the Country Music Association of America contest. After performing at the national level of that contest, she decided to form a band and released her debut album in June of 1999, Time Will Tell. Her follow-up album, See What You Do, was released in June of 2000. The success of both albums also helped earn her opening gigs with artists like Alabama, Jo Dee Messina, Billy Ray Cyrus, Tanya Tucker, and Joe Diffie.
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