Green’s Dictionary of Slang

1. euph. for a town’s ‘red-light’ area.

1894

Reno (LV) Weekly Gazette and Stockman 16 Aug. 1/5: Another one of the girls on ‘easy street’ [...] got tired of her life and tried to end it last Wednesday with a dose of ‘yen she’ (dregs of opium).

2. a secure, comfortable life; a situation free of problems, esp. material ones, usu. in phr. on easy street.

1889		N.Y. Times 23 Sept. 5: At San Jose the other night ‘Easy Street,’ a new comedy, was given a first production and went very well.
1894		R. N. Stephens Life And Adventures Of Steve Brodie, B. J. 22: As a result he found himself, after having twice worked his way to ‘Easy Street,’ about as poor as he ever had been in his life.
1901		John W. Parks ‘My Susie’ 🎵 I’ll be your own fond honey, / If you will furnish money. / We will live on Easy Street.
1912		Sport (Adelaide) 15 June 6/1: They say Johnny sits behind a nice dry bit and could live in Easy Street for the rest of his natural .
1913		J. London Valley of the Moon (1914) 230: A hundred. That’s what I fought for. It’d a-put us on Easy street for a while.
1920		Ade Hand-made Fables 233: He had signalized his arrival on Easy Street by purchasing a swell Ring of several Carats.
1926		Western Dly Press 9 Mar. 10/4: Easy Street. ‘No one in this street has paid rent, or rates for several years’ it was stated during the hearing.
1932		New Call (Perth, WA) 7 Apr. 3/1: In days that were, big hazard schools flourished in most of the States and the men who made money by running them are in ‘Easy-street’ to-day.
1935		(con. 1920s) J.T. Farrell Judgement Day in Studs Lonigan (1936) 606: I know it’s going to set me up sweet and pretty on Easy Street.
a.1948		(con. early 1930s) C. McKay Harlem Glory (1990) 52: Stop kidding, sweet-back [...] Can’t I see you’re on easy street, you hot dog.
1951		Dundee Courier 22 Aug. 2/6: Champions in Easy Street.
1959		C. Himes Crazy Kill 44: After six months she’d hooked Johnny and landed on easy street.
1965		L. Bruce How to Talk Dirty 70: It was Easy Street from now on.
1878–9		A. Garcia Tough Trip Through Paradise (1977) 172: Maybe next day he is again on easy street.
1979		Fantastic Four Annual 8: I’m sick an’ tired of pinchin’ pennies when we could be livin’ on easy street.
1985		B. Humphries Traveller’s Tool 18: Our home-grown Oz fillum producers were on Easy Street, Fat City.
1994		T. Willocks Green River Rising 105: Guys used to pay me to work in this place. I was on easy street.
2001		K. Sampson Outlaws (ms.) 8: For a while we was on easy street with all the tom in Manchester.
2007		(con. 1962) E. Bunker Stark 13: The next score [...] would put him on easy street.
2022		J. Hannaham Didn’t Nobody Give a Shit 106: I’d be on Easy Street, move outta that house next week.

3. (N.Z. prison) a prison’s low security wing.

2001

D. Looser Boobslang [U. Canterbury D.Phil. thesis] 64/2: easy street n. the low security wing of a prison.