In 1996, Amy Sky released her 2nd breakthrough album "Cool Rain" (her first, 1989's "A Breath Of Fresh Air" was shelved and finally released around 2010)and starred in a Toronto production of the musical "Blood Brothers" with David Cassidy and Michael Burgess. After being nominated for two Juno Awards, including best songwriter and best new artist, she released "Burnt by the Sun" in 1998, which also earned a nomination for best songwriter. The string of radio hits these albums produced garnered her three SOCAN awards. 2001 saw the release of "Phenomenal Woman", which was followed in 2003 by Sky's fourth album, "With This Kiss", a romance collection. In 2007, EMI released "Life Lessons: The Best of Amy Sky". In 2008, Sky released a holiday album, "The Lights of December". Between 2005 and 2012, she focused on her songwriting and producing for other artists.