Green’s Dictionary of Slang

the good life, a comfortable existence.

1911		Hartford (CT) Courant 6 Dec. 1: (ProQuest Historical Newspapers) The famous wild cow of Cromwell is no more. After ‘living the life of Riley’ for over a year [...] the cow today fell a victim to a masterfully arranged trap, and tonight lies skinned.
1914		T.A. Dorgan in Zwilling TAD Lex. (1993) 54: He’s leadin’ the life of Reilly that cat is.
1918		in Syracuse Herald 29 July n.p.: This is surely one great life. We call it the life of Riley. We are having fine eats, are in a great detachment and the experience one gets is fine.
1919		H. Pease ‘My Name Is Kelly’ 🎵 Faith and my name is Kelly Michael Kelly, / But I’m living the life of Reilly just the same.
1922		Eve. World (NY) 14 Oct. 8/2: [headline] 13-Year-Old-Boy Leads Life of Riley as Stowaway.
1931		W.N. Burns One-Way Ride 310: I’ve got plenty money – yes. But if you think I live the life of Riley you’ve got another think coming.
1934		V.G. Burns Female Convict (1960) 56: Pretty soft! The life of Reilly!
1939		Wodehouse Uncle Fred in the Springtime 10: Pongo was familiar with the expression ‘living the life of Riley,’ and that it was a life of this nature that The Subject had been leading.
1944		A. Kapelner Lonely Boy Blues (1965) 79: You get dames, good grub, goddam good clothes [...] It’s the life of Reilly!
1952		Lait & Mortimer USA Confidential 150: While ‘confined,’ the prisoners or patients live the life of Riley in private rooms with specially prepared meals.
1966		P. Boyle At Night All Cats Are Grey 217: There was the life of Reilly! Owing no allegiance to anyone.
1977		T. Ronan Mighty Men on Horseback 94: The snake lived mainly down in the hold or the bilge and led the proverbial Life Of Riley.
1979		New Musical Express 17 Nov. n.p.: I was living this lovely life of Riley, where I was just listening to the music I liked.
1981		B. Behan ‘The Last of Mrs Murphy’ in After the Wake 18: They had the life of Riley down on the quay, while it lasted.
1990		(con. early 1950s) J. Ellroy L.A. Confidential 257: Mickey languishes in his cell, living the prison life of Riley.
2005		M.B. ‘Chopper’ Read Chopper 4 108: Polish Suzie plans to live the life of Riley with her Norwegian boyfriend.
2021		A. Parks April Dead 99: ‘Staying here in the big house with you making his dinner every night, no boss to tell him what to do. Life of Riley’.