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| Title | Artist | Medium & Support | Creation Date |
| Untitled (Gold Boot, To Buzz Miller) | Warhol, Andy | Watercolor, ink, and collage on paper | 1958 |
| Freedom, A Fable: A Curious Interpretation of the Wit of a Negress in Trouble Times | Walker, Kara Elizabeth | Illustrated book | 1997 |
| Let's Talk | Piper, Adrian | Screenprint on paper | 1992 |
| The Boot Black | Bishop, Isabel | Graphite on paper | 20th century |
| Lady Catherine to Elizabeth Bennett, from Pride and Prejudice | Bishop, Isabel | Pen and wash on paper | 1944 |
| Boys Selling Newspapers | Sloan, John | Charcoal and graphite on wove paper | 1903 - 1916 |
| I was Cleopatra Once, She Said, from the book "Archy and Mehitabel" | Herriman, George | Pen and ink on paper | 1930 |
| Illustration from the book "Archy and Mehitabel" | Herriman, George | Pen and ink on paper | ca. 1930 |