When you say that somebody is “living” or “leading the life of Riley”, what you are implying is that he/she is leading a very comfortable life. He/she is leading the kind of life that all of us wish we had — a life where one doesn’t have to work hard, or spend sleepless nights worrying about making ends meet. When you lead the life of Riley you lead a very “cushy” life.
Here are a few examples. * While Prabha worked all day, Sunil stayed home living the life of Riley. * The young couple moved into a big house and led the life of Riley. Origin of this expression: Well, no one is really sure as to who this Riley was. Some scholars argue that this Riley (originally spelt “Reilly”) referred to the character that appeared in a song written by Pat Rooney in 1890. In the song Riley says if he ever became the President of the US then “New York” would “swim in wine when the White House and Capitol are mine.” It tells you something about the kind of President he would have made, doesn’t it? Some others argue that it was an American poet by the name of James Whitcomb Riley who gave rise to this idiom. Apparently, Riley (1849-1916) wrote sentimental poems about young boys, which were very popular during his time. The poems told the stories of young boys lazing around during the summer without a care in the world — wandering about barefoot, swimming in the river and fishing.