The origins of the phrase in question are somewhat ambiguous, but the general consensus is that it refers to one who lives or has lived a relatively prosperous life. No matter where the phrase was birthed, it has found universal acceptance as a catchphrase for one who leads a blessed life, if not one of ease. Although it is rather dated, 'the life of Riley' is one very familiar to this writer, as to many who follow in the footsteps of Jesus who was the Messiah of Israel & are willing Vessels of His Glory!
Some may accuse me of arrogance, even of dishonesty, but I believe that when we love our neighbor as we love ourselves & treat others as we would like them to treat us, we will, more often than not, receive blessings in accordance to those we freely bestow! This is a verily Scriptural principle, one espoused & practiced by Jesus Himself. Many there are who, when faced with trials & tribulations, like to blame it on some outside force ( such as 'Satan' ), not willing to accept the responsibility for their own actions or failures.
Some Christians are their own worst enemies; they have missed the forest for the trees, so to speak! So intent are they on what they call our 'Final Reward' that they are often blinded to the importance of being human. We were not awoken simply so that we could go to some place called 'Heaven' when our biological bodies perish; we were placed on this earth to spread the Good News that the Creator has deemed to live in relationship with the Creation!
Life, when you think about it, is ALL about relationship; whether good or bad, relationship defines our very existence! You've no doubt heard the phrase, 'no man is an island'. While it is possible to live as a hermit for a time, it is impossible to live for ANY length of time without the blessings of some sort of relationship. Human beings, in order to sustain biological life, must rely on some sort of relationship, even if they have the capacity to rule their own provender. There are plenty of ready examples out there of men & women who have withdrawn from society for a time to follow their own pursuits, to make their own way, in a manner of speaking.
Try as you might, there is no way to live in this world without relying on relationship; relationship sustains all life! Just as a plants wilts & dies without the proper combination of soil, water & sunlight, so this human experience cannot persevere without relationship of some sort! One MUST have relationship with others in order to sustain life. Anyone who believes they can make it own their own, if they're honest with themselves, soon finds themselves to be dead wrong. Life was meant to be lived & it cannot be without relationship of some sort, good or bad. Even a bad relationship may sustain life for a time, but if it does not turn to good, the life sustained, like a plant, will wither & die!
There are countless people out there who seem to think that they can call themselves Christians & yet live without the Communion enjoyed by the Body of Christ! Without the necessary relationship with those of like faith, the Faith of Christ, they will soon begin to lose the vigor of those associated with the Body. By cultivating the necessary relationship with the Community of Faith, our humanity will flourish & bear fruit to the advancement of the Kingdom of our God & Father!
Life, when lived according to the basic principles given earlier, from the teachings of Jesus, is blessed beyond measure! This is not to say that if you do everything right, you will be living on easy street all the time; by no means, but when one lives by these principles, religiously, one will begin to realize the silver linings to every dark cloud. They will begin to take responsibility for their own actions or inaction & rather than blaming all their problems on someone or something else, will begin to learn from their mistakes & draw strength from trials & tribulations!
As humans, being Vessels of His Glory, willing or unwilling, we get to choose whether we will live a blessed & prosperous life, or whether we will be an adversary to ourselves & fail to grow where we are planted. To a great extent, humanly speaking, how we face our challenges ( we ALL have them ) determines whether we live 'the life of Riley', if we wither & die. I don't know about you, but no matter the challenges I face; I want to live!
Charles Haddon Shank