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James Whitcomb Riley. com responds to FAQ about the expression "The Life of Riley." 

The expression got started in the 1880's about the time that James Whitcomb Riley started depicting the comforts of a well ordered and prosperous home life in his poems.  These poems were of course very popular.  He "lectured" on them in tours around the country in every city before great numbers of lyceum circuit audiences. Think of "An Old Sweetheart of Mine" who was not just a dream to the gentleman persona of the poem  but who actually was the wife of the dreamer.  What good luck to live in a place where dreams can be true, where homes are happy and the comforts of home life can be experienced!  Why doesn't this happen to me??? We also think of Riley's poems of barefoot boys and girls on lazy summer days, etc.,etc.

 Anyway, the ideal life of carefree, bountiful and yet humble lifestyle and life of "homey dream-come-true" spawned  a comic song by Pat Rooney of the name "The Life of Riley" in the 1880s.  The popularity of the song and the continued popularity of Riley's poems of the nature depicted reinforced each other and led to the entry of the phrase into the American vernacular.  Sue Chapman.

Note:  I remember a television show of this name too. Seems like it might have been in the 50's??? Editor.  A boy living "The Life of Riley" is shown below.

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Click on this thumbnail to bring up the enlarged scan and then click your browser's back button or arrow to return to this page. This is an example of a a book cover of one of Riley's books.  They were the first in the country to use illustrations and helped make Riley's books so popular.  In fact many (such as this one- where we found it) were framed and hung in front rooms at the turn of the 20th century.