In 1935 a man won an Oscar for a film called How to Sleep, in which he essentially napped on camera. That man was Robert Benchley, who publicly claimed to be profoundly lazy while producing over 600 essays, 48 short films, and reshaping how an entire nation laughed. The contradiction is the whole story.

We dig into whether Benchley was the patron saint of failing upward or whether his lazy, befuddled persona was a meticulously crafted shield protecting a sensitive, fiercely moral man. From a devastating childhood loss to the Algonquin Round Table to Hollywood, we trace how grief built a comic mask that still shapes comedy today.

• The crushing childhood moment when his mother cried that the wrong son had died, and how it forged his unthreatening persona
• His Harvard graduation essay written entirely from the point of view of ...