In the ghost-hunting community, this mournful spirit is known as "Our Lady of the Spoons of Damocles."  From UNC Chapel Hill's 1970 yearbook.

"He followed her into the tree."  From The Enchanted Bird by Antoinette Decoursey Patterson and illustrated by Elizabeth Pilsbry, 1917.

From Saint Mary's 1937 yearbook.

Poseidon's sea serpent appears in the next panel.

Cassiopeia figures into the previous panel.

From Magazine of Horror, 1969.

We checked, and it turns out to be true -- happiness is, indeed, an overhead projector, and as this technology becomes increasingly obsolete, sadness spreads across the globe.  From Wake Forest's 1975 yearbook.

Reblog if you ride a budget turtle or sometimes go out in your shell.  From L'Impartial de l'Est, 1905.

From The Foolish Almanak, 1906.

"I am naughty."  From Colorado College's Nugget yearbook of 1954.

Like caterpillars spinning wombs out of sunlight, so are the days of our lives.  (By the way -- notice the tree bark -- dozens and dozens of caterpillars are inching their ways up the trees!)  From Lustige Blätter, 1918.

As a general rule, never hold your marotte upside down in front of a giant skull with a sword piercing one eye.  An ounce of prevention and so on.  From Tulane's 1896 yearbook.

A ghost toast.  From Le Courrier Français, 1889.

From Washington University's 1909 yearbook.  See How to Hoodoo Hack a Yearbook.

From Cine-Mundial, 1935.  See Crossroads Chiromancy: The Secrets of the Glowing Red Hands.

From Swarthmore's 1932 yearbook.

From A Book of Fairy-Tale Foxes by Clifton Johnson and illustrated by Frank A. Nankivell, 1914.