In 1993, Cassidy was honored by the Washington Area Music Association with a Wammie award for the "Vocalist Jazz/Traditional" category. The next year she was invited to perform at the event and chose to sing "Over the Rainbow". A "Washington Times" review of the event called her performance "a show-stopper". She took home two Wammies that night, again for "Vocalist Jazz/Traditional" and also for "Roots Rock/Traditional R&B". For a brief period that year, Cassidy signed a deal with Blue Note Records to pair up with pop-jazz band Pieces of a Dream to release an album and tour the country. She sang two tracks in a mainly instrumental album. It was a musically unsatisfying experience for her.