Part of the fourth-grade curriculum in the author's district is the creation of a self-portrait. This is always a challenge for both the students and the author, because it is so difficult for beginners to draw a satisfying drawing of a face, whether it is their own or someone else's. In the past the author tried many formats and materials to make this lesson more successful and fun, including learning to mix tints and shades in painted portraits, and constructing Cubist-style abstractions in collage. This year, with a special focus on the arts of Africa, in which the masks were especially appealing to students, the author tried something different. She combined a classic lesson on portraiture with the creation of a mask. To get them thinking, she showed a video about the variety and uses of masks in all cultures. With Halloween just around the corner, the lesson was further enhanced by timing, since the holiday always gets the students thinking about and looking at masks. This lesson in portraiture enabled her students to understand and appreciate the mask as an art form.