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Where did that come from - Live the life of Riley
Stan St. Clair

Though archaic now, in the 1950s this was still very common in the U.S. to mean a life of ease and prosperity. This phrase, according to some, was popular as far back as the 1880s in England, when the poems of James Whitcomb Riley depicted comforts of prosperous home life. 

Indeed, he may have been the original “Riley.” It was spread with the Irish/ American soldiers in the U.S. Army during World War II.

The first known published citation is in a letter from a Pvt. Walter J. Kennedy who was stationed at Camp Dix, New Jersey, which was published in The Syracuse Herald on June 29, 1918 under the heading, “Great Life, Writes Soldier at Camp.”

“This is surely one great life. We call it the life of Riley. We are having fine eats, are in a great detachment and the experience one gets is fine.”

Later that year The Bridgeport Telegram published a letter from Pvt. Samuel S. Polley, who was stationed in France.

“They [German officers] must have led the life of Reilly as we caught them all asleep in beds ...”

The phrase reached the wider public via the 1919 song by Howard Pease:  

“My name is Kelly:                                                                                                                      “Faith and my name is Kelly, Michael Kelly, but I’m living the life of Reiley just the same.”