| River Vista | | 1936 | | | |
| Riverside Plant | | 1928 | | | |
| Rivulet | | 1936 | | | |
| Road to Bafwasende | | 1933 | | | |
| Road to Berlin Heights | | 1929 | | | |
| Road to the River | | 1933 | | | |
| Road to the Valley | | 1928 | | | Third Prize |
| Road to the Valley, Kinsman Road. | | 1919 | | | |
| Roadside Landmark | | 1935 | | | |
| Roaring Bessemer | | 1931 | | | |
| Rockport Harbor | | 1937 | | | |
| Rocks and Clay | | 1938 | | | |
| Rocks and Fog | | 1924 | | | |
| Rocky Inlet | | 1938 | | | |
| Rocky River | | 1925 | | | |
| Rocky River Valley | | 1919 | | | |
| Rodolpho | | 1926 | | | First Prize |
| Rolling Hills | | 1930 | | | |
| Rolling Hills | | 1930 | | | |
| Romance of Steel | | 1928 | | | First Prize |
| Romsdalen, Norway | | 1924 | | | |
| Roofs | | 1936 | | | |
| Rooftops in Frankfurt | | 1931 | | | |
| Rose | | 1931 | | | |
| Rose Lake | | 1936 | | | |
| Roses | | 1939 | | | |
| Rosina | | 1930 | | | Third Prize |
| Rough Country | | 1931 | | | |
| Roumanian Rhapsody | | 1939 | | | |
| Round about Cleveland | | 1937 | | | Honorable Mention |
| Round Brass Box with Enamel | | 1927 | | | |
| Round Copper Box | | 1927 | | | |
| Round Pewter Box | | 1933 | | | |
| Roundhouse Rays | | 1936 | | | First Prize |
| Rounding the Bend | | 1932 | | | |
| Roviana | | 1925 | | | |
| Ruby | | 1929 | | | |
| Ruby | | 1930 | | | |
| Ruby | | 1931 | | | |
| Rue De L'Asile de Nuit | | 1931 | | | |
| Ruff Takes a Nap | | 1930 | | | First Prize |
| Ruins | | 1933 | | | |
| Ruins of Athelstan | | 1925 | | | Honorable Mention |
| Rural | | 1935 | | | |
| Rural Architecture | | 1939 | | | |
| Rural checkerboard | | 1938 | | | |
| Rural Hospitality | | 1934 | | | Honorable Mention |
| Rush Hour | | 1939 | | | |
| Rushing Water | | 1939 | | | |
| Russian Dancers | | 1929 | | | Third Prize |
