[2] Originally from Mississauga, Ontario, Cullen released her debut album Garden Path in 2000.
[3] She followed up with So Much, an album of jazz standards, in 2002,[4] before returning to original folk-pop songwriting for 2004's Uneven Hill.
[5] During her early career, she kept these two sides of her artistic personality separate, recording distinct albums and distinguishing her live performances as being either folk or jazz shows; during her tour to support Uneven Hill, however, she decided to instead start integrating the two genres.
[6] Her song "Away So Long", cowritten with Brian MacMillan, was the winner of the 2005 Colleen Peterson Songwriting Award.
Her next album, 2006's Calling for Rain, was an album of covers of artists such as Joni Mitchell, Gordon Lightfoot, Richard Thompson and Randy Newman, done in a style that incorporated both pop and jazz influences.