My Grandmother, Pitseolak, Drawing represents Pitseolak Ashoona (about 1904-1983), grandmother of the artist Annie Pootoogook, sitting in bed and drawing the landscape seen through a window. The room and its contents are rendered in simple lines. Some details, like the speckled flooring and the quilt seams, contrast with the large coloured surfaces. As usual, Pootoogook diverges from traditional Inuit imagery to depict the reality of everyday life in Cape Dorset. By referring to her grandmother, she underscores her artistic heritage and highlights drawing as a means of cultural resilience.

Born into a family of Inuit artists, Annie Pootoogook began her career at the Kinngait Studios, in Cape Dorset. She is renowned for drawings that chronicle the everyday life of her community, some depicting violence or domestic abuse. Gaining recognition in the Canadian contemporary art milieu, she won the Sobey Art Award in 2006. The following year, she was invited to Documenta 12, becoming the first Inuit artist to participate in the contemporary art exhibition held every five years in Kassel, Germany. Pootoogook died tragically in Ottawa in 2016, leaving a widely acclaimed artistic legacy.