Robert E. Sherwood won the Pulitzer Prize for Drama three times (1936, 1939, 1941).
| Year | Contest | Category | For | Sources |
|---|---|---|---|---|
| 1941 | Pulitzer Prize for Drama | Pulitzer Prize for Drama | There Shall Be No Night | 1 · 2 |
| 1939 | Pulitzer Prize for Drama | Pulitzer Prize for Drama | Abe Lincoln in Illinois | 1 · 2 |
| 1936 | Pulitzer Prize for Drama | Pulitzer Prize for Drama | Idiot's Delight | 1 · 2 |