Also in 2006, Hewlett wrote and starred in the off-Broadway production of Humans Anonymous, and the winner of Best of Fringe and Best Ensemble at the Toronto Fringe Festival.
In 2012, Hewlett was cast in the Canadian teen drama series Degrassi: The Next Generation as Margaret Matlin, a role she played until 2014. In 2013, she starred in Jeremy Lalonde's low-budget comedy feature film Sex After Kids. In 2014, she was cast in the comedy television series The Stanley Dynamic as Lisa Stanley and in 2016, she guest starred on the Starz series The Girlfriend Experience, based on Steven Soderbergh's film of the same name.
