How to Sleep is a short comedy film written by and starring humorist Robert Benchley. Filmed and released by MGM in 1935 (as part of their "Miniatures" series), it features Benchley as a narrator as well as film subject, discussing four parts of sleep -- causes, methods, avoiding sleep, and waking up.

The production was inspired by a Mellon Institute study on sleep commissioned by the Simmons Mattress Company. It was filmed in two days, and featured Benchley as both the narrator and sleeper, the latter a role Benchley claimed was "not much of a strain, as [he] was in bed most of the time." Benchley was in fact a last-minute participant. As his son Nathaniel Benchley recalled, "How to Sleep was supposed to be a Pete Smith short, but Pete Smith was sick. It was going to be a thing on Simmons mattresses; they had this film of quick shots showing how many positions you take during an evening's sleep. They tried to have somebody else do it, who couldn't make it, and they finally came to my father and asked if he would try to do it. That's what finally wound up being How to Sleep."The film was well received in previews and was promoted heavily, with a still from the film being used in Simmons advertisements. The only group not pleased was the Mellon Institute, which did not approve of the studio mocking their study.How to Sleep won an Academy Award for Best Live-Action Short Subject in 1935. MGM kicked off an entire series of situation-comedy reels, each 10 minutes in length, showing Benchley giving mock-instructional lectures (How to Be a Detective, How to Rest, etc.) or coping with household situations (An Evening Alone, Home Movies, etc.).

How to Sleep is included as an extra on the DVD of the 1935 Marx Brothers feature film, A Night at the Opera, and is also available on the DVD set The Robert Benchley Miniatures Collection.