The earliest example of a playbill is this one from the Charleston Theatre in 1805 (huh, who knew smo(a)king wasn’t allowed).
This one from 1821 is for William Macready at the Theatre Royal, Covent-Garden in London. Macready was the preeminent Shakespearean actor in England of the early 19th century. His first tours of the US (in the early 1840’s) were a rousing success.
This engraving is of Edwin Forrest, the leading American actor of the early 19th century. He and Macready (above) began a feud in the mid-1840’s that became quite vicious…
So vicious, in fact, that during Macready’s last tour of the US in 1849, supporters of Forrest used immigrant/nativist tensions to spark the Astor Place Riots of May 10, 1849, that killed over two dozen and injured over a hundred. The story is fascinating and is well explored in Nigel Cliff’s The Shakespeare Riots.
The next few playbills are for Edwin Booth, the greatest American Shakespearean actor of the second half of the 19th century.
Not satisfied with being an actor, Booth also became a theatrical entrepreneur, building his own theater, modestly (not) named Booth’s Theatre in New York.
Though the preeminent American actor of the late 19th century, he is mostly remembered now as the brother of Abraham Lincoln’s assassin, John Wilkes Booth.