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File consists of audio-visual material relating to Winsom's exhibitions and projects. Optical disks contain a digital catalogue for Rousings (2004) featuring Winsom's artist statement, video footage from the opening of Iconography of Divination (2003) at the A Space Gallery, and "OYA + Yemaya," a movie by Winsom. Also includes the movie All Eyes on Africa (1993) by Clem Marchall on VHS and a VHS tape titled "Interview Grand Cayman - Looking for perfect teachers 2004."

File contains a binder that was made for Winsom's 50th Birthday, containing notes and letters from friends and family. Includes the letter that was send out inviting people to participate, invitations to a party that was held at A Space Gallery to celebrate Winsom's Birthday, and party guests' notes to Winsom. Winsom's headshot is attached to the cover of the binder.

File consists of textual records relating to Winsom's grant applications and awards, as well as grant and award programs that Winsom sat on the jury for or participated in. Includes records relating to the Toronto Arts Council Foundation 2002 Awards, an invitation to a Gala Dinner for the Minister's Forum on Diversity and Culture (2003), a schedule for the ceremony relating to Winsom's Honorary Doctorate from OCAD University (2015), and related documents. Also includes records relating to Winsom's participation in the jury for the First Visual Arts Students Awards for the North York Board of Education in 1995, the Mid-Career Artist's Grant from the Ontario Arts Council in 1999, and a program for the 17th Annual Harry Jerome Awards in 1999. Winsom was commissioned by The Black Business & Professional Association to create a work for the Harry Jerome Awards, which is discussed on page 3 of the program under the title "The Fabric of Life."

File consists of records relating to Winsom's exhibitions and projects, predominantly in the 2000s. Includes promotional material such as brochures and flyers, as well as other ephemera. Includes records relating to The LOMO Project: Toronto is Neighbourhood at A Space Gallery, Omiala: A Festival of New Black Culture (2004), the Spirits of Power art auction, Niagara: Between Time and Place (2000), and others.

File consists of an instructional document relating to photocopy lifts, a type of image transfer created using a matte or gloss liquid medium. Also includes colour and b&w prints on vellum and one emulsion transfer on a canvas panel that Astman used in teaching. Two of the vellum prints are taped to a poster board for display in the classroom.

File consists of instructional teaching documents regarding transferring images onto fabric using freezer paper, four prints of image on fabric pieces, and samples of freezer paper. Also includes one colour print on tissue paper.

File consists of a black and white image transfer print of an image of a backyard or garden, made using Liquid Light from the Rockland Colloid brand, a b&w photographic emulsion.

File consists of "The Deadline" (1996), a comic created by Helene Astrom (Contemporary Photography Department at OCAD), a production still from Blackmail (1929), directed by Alfred Hitchcock, two emulsion transfers and instructional documents regarding image transfers.

File consists of an image transfer print from "Scenes from a movie for one," on a metal plate coated in encaustic wax that Astman used in teaching. The plate was originally wrapped in a sheet of paper with handwritten notes.

File contains personal records relating to Winsom's travels and activities. Includes a photocopy from a Belize travel guide, a flyer for Whisky Hill Craft Gallery, records relating to celebration of life services for Madgery and Leonard Gardner, and other event invitations and travel records. Also includes a series of loose pages of math notes that are unlabeled, but are possibly Winsom's schoolwork, or work that she graded as an instructor.