Here's a cuneiform machine from Le Rire, 1903.

Writer's block is actually a fear of death.  From Ulk, 1919. 

"It was to be the effort of his life," from Ghosts I Have Met and Some Others by John Kendrick Bangs, 1898.

You've heard the ocean in a seashell, but listening to a tiny typewriter offers descriptive (if grandiose) reports of seaside conditions.  From Jugend, 1911.

"And sat looking at it far into the night."  From A Stumble on the Threshold by James Payn, 1893.

From Die Muskete, 1914.

You've heard of "the diminishing size of the typewriter market" (over at Wikipedia's entry on the Smith Corona), and it's true: it's the market that got small, not the typewriter.  The caption to this postcard reads: "The 14-ton giant Underwood Master operating daily at the New York World's Fair 1939."

By John Francis Knott for the Dallas Morning News, June 7, 1945 (scanned by the DeGolyer Library).

Here's how writer's block works, from Tommy Toddles's Comic Almenak, 1862.

From Songs of Singularity or Lays for the Eccentric by the London Hermit, Walter Parke, 1875.

From Love's Provocations by Cuthbert Bede, 1855.

This unusual typewriter keyboard layout offered a way to take dictation from a dictatorial dictator.  John Savard tells us that "in 1937, Portugal's dictator Antonio Salazar decreed the use [of this keyboard]."  

Was an Underwood typewriter once elected president of the United States?  Election Administration deputy director William C. Kimberling explains: "In the evolution of the Electoral College, there have been some interesting developments and remarkable outcomes.  Critics often try to use these as examples of what can go wrong.  Yet most of these historical curiosities were the result of profound political divisions within the country which the designers of the Electoral College system seem to have anticipated as needing resolution at a higher level."  Our illustration appears in Business Journal, 1912, p. 26.