During his first two years at Harvard, Benchley worked with the "Harvard Advocate" and the "Harvard Lampoon". He was elected to the "Lampoon"s board of directors in his third year. The election of Benchley was unusual, as he was the publication's art editor and the board positions typically fell to the foremost writers on the staff. The "Lampoon" position opened a number of other doors for Benchley, and he was quickly nominated to the Signet Society meeting club as well as becoming the only undergraduate member of the Boston Papyrus Club at the time.