Newspapers were blowing about the road and pavement, and Broadway looked seedy, like a slovenly woman just out of bed. On almost every street corner there were elevated chairs with shoe-lasts sticking up and people sitting comfortably in shirt-sleeves getting their shoes shined. They gave one the impression of finishing their toilet on the street.

Charlie Chaplin
From: My Autobiography (Simon & Shuster, 1968)

2010 | San Francisco Transbay Terminal
Photograph by Shawn Clover

1857 | Honoré Victorin Daumier
Mr. Hume fantasizing about Julius Caesar polishing his boots

19th Century | The Little Shoe-Shine Boy
By Comte de Charles Philibert Lasteyrie du Saillant

On a more sober and necessary note, ready and waiting on the streets leading into the City that were tramped every morning by ranks of City workers, were rows of shoeblacks: in the days before routine street paving, every respectable worker needed to have his shoes cleaned after walking to work. In the early part of the century, blacking, or shoe polish, came in liquid form, and boys equipped themselves with paintbrushes, enquiring, ‘Japan your shoes, your honour?’ Blacking paste became available in cake form from the 1820s. 
Judith Flanders
The Victorian City. Everyday Life In Dickens's London (Atlantic Books, 2012)

From The Album "Street Life In London"

It was so easy to use that shoeblacks vanished from the streets, but in 1851 the Ragged School set up a Shoeblack Society, and soon their red-coated shoeblacks were seen throughout the city at fixed pitches. The charge was 1d for brushing a gentleman’s shoes and trousers, from which the boys earned about 10s a week in summer but in the winter only half that. (This is surprising: one would have expected the wet season to require more shoe-cleaning, not less.) 
Judith Flanders
The Victorian City. Everyday Life In Dickens's London (Atlantic Books, 2012)

1922 | Le Prix Courant magazine
Montreal, Canada

1935 | Fortune magazine | Grand Central Station

1937 | Shoe-Shine Stand Built Like Merry-Go-Round

That’s probably one of the most direct messages in the world (“If You Don’t Work You Can’t Eat.”, ED). You know, a man looking for a job today looks for a special kind of job; he should first go get a job. I started as a janitor, a shoeshine boy. I shined shoes in front of a radio station—27 years later I came back and bought the station. 
James Brown
Interviewed by Glenn O'Brien (Interview October 1984)

CA.1911 | Baker Shoe-Shine Stand | Anaheim, California
Source: CaliSphere, University Of California

1955 | Vivian Maier | Untitled (Boy shining shoes)
Source: 1stdibs.

2010 | Shoeshine stand | 12th Street | Oakland, CA
Photograph by Lauren Crabbe

1877 | John Thompson & Adolphe Smith
The Independent Shoe Black

And now a word from our sponsor:

1942 | Claire Trevor for Shinola
Golf shoes by I. Miller

1942 | Shinola Cleaner and I. Miller shoes from I. Magnin, Hollywood