Living the life of Riley means living the easy life, an existence marked by luxury and a carefree attitude. The term living the life of Riley is an American phrase, it first appeared in the early 1900s. There is some suggestion that the idea of a gentleman named Mr. Riley enjoying a luxurious, easy life is suggested in several earlier vaudeville songs, though the phrase living the life of Riley appears slightly later. In the beginning, Riley was also spelled as Reilly, the only spelling now recognized by the Oxford English Dictionary is living the life of Riley. The term living the life of Riley spread across American training camps during World War I, soldiers wrote home using the phrase, which popularized it. By the 1940s the term living the life of Riley was well known enough to be used as the title of a popular radio comedy, The Life of Riley, starring William Bendix. Note that Riley is a proper name, and is therefore capitalized.
Most of that was Malaysian taxpayers’ money and it was used to buy artworks and fancy real estate, make a movie, and generally allow its youthful directors to lead the life of Riley. (The Myanmar Times)
Murderer Cameron Mansell is “living the life of Riley” with ready access to a computer and television as a medium security prisoner while withholding the location of his victim’s body, according to the dead man’s father Laurie Puddy. (The West Australian)
By contrast, the similarly aged, similarly divorced and similarly dating George Clooney was depicted as a merry bachelor living the life of Riley. (The Guardian)
Shameless: Meet the shoplifter mum who lives the life of riley paid for by YOU (The Daily Express)