dr_fission wrote at 2008-06-10 22:49:45
The earliest reference date to the actually phrase "Life of Reilly" that was mentioned in the previous answer, 1919, corresponds quite nicely with the arrival in New York of the famous British foreign agent, Sydney Reilly. He was a Russian Jew (or Jewish Russian if you prefer) who played fast and loose with both his considerable accumulated wealth and the laws of whatever country he happened to be in. His motives were honorable, but his methods were questionable at best. Regardless, he was as flamboyant as he was mysterious. Reilly was the character upon which Ian Fleming based his popular spy novel series, James Bond.
Gena O'Leary wrote at 2009-03-30 04:31:20
The phrase 'Living the Life of Reilly' is actually much older than the 1880's. In Ireland during the 1300's the O'Reilly clan gain influence in the church and even had their own mint. At that time all coinage throughout Ireland was known as Reilly's. Of course this was declared illegal coinage by the English. However, the times were so good that the saying developed, hence 'Living the Life of Reilly' sometimes used or heard as 'Life of Riley.'