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| Title | Artist | Medium & Support | Creation Date |
| Boys Selling Newspapers | Sloan, John | Charcoal and graphite on wove paper | 1903 - 1916 |
| Zizi | Castaldo, Amaylia Chlarina | Charcoal on paper | 1906 - 1987 (artist life dates) |
| Lesbian | Castaldo, Amaylia Chlarina | Charcoal on paper | 1906 - 1987 (artist life dates) |
| Margaret | Castaldo, Amaylia Chlarina | Charcoal on paper | 1906 - 1987 (artist life dates) |
| The Mystic Return | O'Brien, Edward | Silverpoint, graphite, and ink on paper | 1974 |
| Portrait of Artist's Wife | Trebilcock, Paul | Black chalk on paper | 20th century |
| Woman Seated in a Wicker Chair | Sargent, John Singer | Pen and ink on wove paper | ca. 1920 |
| Couple on a Park Bench #16 | Bishop, Isabel | Pen with wash on wove paper | ca. 1945 - 1947 |
| Two Girls at a Soda Fountain (recto); Man and Woman Seated (verso) | Bishop, Isabel | Pen and wash on paper | ca. 1950 |