First of all, who was he? Impossible to say for sure. My usual sources cannot, in fact, even agree on the spelling of the name: while most agree that it is Reilly, two of them suggest that it is Riley, and there is even one candidate for O'Reilly! Good Irish names, all of them, but the expression, in fact, was coined on this side of the Atlantic. Whether his name was Reilly or O'Reilly, the person referred to seems to have been a character in an American song popular in the late nineteenth or early twentieth century.

There are two candidates: one, "Is That Mr. Reilly?" comes from 1882 and was written and performed by the vaudeville performer Pat Rooney. It concerns what the hero of the song, a man named Riley, would do if he suddenly struck it rich, promising, among other things to "swim in wine when the White House and Capitol are mine": he intends, in other words, to lead the life of Riley! This song was championed as the origin of the expression by John Bartlett, of Bartlett's Familiar Quotations fame, but the critic and essayist H. L. Mencken believed that the expression derived from.yet another song, written around the turn of the century by Lawlor and Blake and titled "The Best in the House Is None Too Good for Reilly." James Rogers, of The Dictionary of Clichés muddies the waters somewhat by telling us that the name of the Pat Roney song was not "Is That Mr. Reilly?" but "Are You the O'Reilly?" and even quotes the refrain:

Are you the O'Reilly who keeps this hotel?

Are you the O'Reilly they speak of so well?

Are you the O'Reilly they speak of so highly?

Gor blime, O'Reilly, you're looking well.

It is quite possible, of course, that Pat Rooney wrote and began performing two songs in 1882, and that they had similarly but not identically named protagonists. Whatever the case, there do seem to have been several songs involving a Riley or Reilly or O'Reilly touring the American vaudeville circuit in the last two decades or so of the nineteenth century, all of them featuring protagonists who could very well have inspired the popular expression: Riley and Reilly are pronounced identically, of course, and the difference between "the life o' Reilly" and "the life o' O'Reilly" when spoken aloud is minimal.So it is quite possible that the hero of one or both (or all three, if there were indeed three) of these songs―and of any other, as yet undiscovered, Riley/Reilly/O'Reilly vaudeville songs from the same period―could be the person referred to. Indeed, it is possible that the protagonists merged in the public mind, and provided the origin of the carefree Reilly of the expression.

But the Reillys (hoever spelled) from the world of vaudeville song are not the only candidates. There remains a contender who was a real person: in the QPB Encyclopedia of Word and Phrase Origins, Robert Hendrickson concludes a mention of the Bartlett and Mencken choices as follows: "Yet the Hoosier poet James Whitcomb Riley (1849-1916) may just lend his name in some way to the saying. Riley's simple, sentimental poems depicting the lives of barefoot boys loafing and living a life of ease in the summer, were immensely popular at the time the phrase came into use." It is true that in past days poetry, especially sentimental poetry of the type Hendrickson describes, had a far greater audience than it has had in latter days. It is even possible that the name of the poet became confused with the vaudeville-song protagonists who led similarly carefree lives.

In Common Phrases and Where They Come From, John Mordock and Myron Korach go a bit farther, suggesting that Riley may have contributed to the expression not only through the carefree, idyllic existence of his characters, but also through the (bad) example of his own life. Noting that the poet is sometimes depicted as "one of the laziest men ever to come out of Indiana," they go on to say

Before his recognition as a poet, his neighbors often wondered about him. He left school at sixteen and occasionally worked odd jobs. He often appeared in the streets of Greenfield, Indiana, more than slightly inebriated, indulging himself with many a lark and spree. In fact, Riley was considered the town loafer. Mothers taught their children not to live the "life of Riley."

A bit fanciful, perhaps, for it does not explain how the expression could have spread beyond Greenfield, Indiana to the whole of North America (and beyond): something the itinerant nature of vaudeville and the wide popularity of Mr. Riley's poetry both do. But who knows for sure? the language develops in wonderful ways!

Incidentally, the expression "Gor blime," pronounced gor-blimey, in the O'Reilly refrain quoted above is a British-English corruption, still used today, of "God blame me [if what I say is not the truth]," and a Hoosier, for those of us who are not Americans, is a native or resident of the American state of Indiana. Why? . . . Well, perhaps another day!

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