The Life of Riley, with William Bendix in the title role, was a popular American radio situation comedy series of the 1940s that was adapted into a 1949 feature film and continued as a long-running television series during the 1950s, originally with Jackie Gleason playing Bendix's role. The show began as a proposed Groucho Marx radio series, The Flotsam Family, but the sponsor balked at what would have been essentially a straight head-of-household role for the comedian. Then producer Irving Brecher saw Bendix as taxicab company owner Tim McGuerin in Hal Roach's film, The McGuerins from Brooklyn (1942).

The Flotsam Family was reworked with Bendix cast as blundering Chester A. Riley, a wing riveter at the fictional Cunningham Aircraft plant in California. His frequent exclamation of indignation became one of the most famous catch phrases of the 1940s: "What a revoltin' development this is!" The radio series also benefited from the immense popularity of a supporting character, Digby "Digger" O'Dell (John Brown), "the friendly undertaker." The expression, "Living the life of Riley" suggests an ideal life of prosperity and contentment, possibly living on someone else's money, time or work.

Rather than a negative freeloading or golddigging aspect, it instead implies that someone is kept or advantaged. The expression was popular in the 1880s, a time when James Whitcomb Riley's poems depicted the comforts of a prosperous home life, but it could have an Irish origin: After the Reilly clan consolidated its hold on County Cavan, they minted their own money, accepted as legal tender even in England. These coins, called “O'Reillys” and “Reilly's,” became synonymous with a monied person, and a gentleman freely spending was “living on his Reillys.” Thus, the radio-TV title has an ironic edge.

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