What does the phrase “on Easy Street” mean and Where does it come from?

The phrase “on Easy Street” means: Having an easy living; in comfortable circumstances; prosperous; riding on the gravy train.

American slang from the close of the nineteenth century.

The earliest record of this imaginary street in the Dictionary of American English takes it to George V. Hobart’s It’s Up to You (1902), in which the author tells of a young man “who could walk up and down Easy Street.”