If someone lives the life of Riley, they have a very enjoyable life because they have plenty of money and no problems. He was living the life of Riley while we had barely enough to eat. It was like paradise. It was just like living the life of Riley. Note: People sometimes use the verbs lead or have instead of live. These people moan about their lives when in reality they're having the life of Riley. Note: This expression often shows disapproval or envy. Note: This expression probably comes from a song `Is That Mr Reilly', which was popular in America in the 1880's and described what Reilly's life would be like if he was rich.