dolefulest

The old gentleman he leaned his elbow on the window - sill, and his head on his hand, and looked out of the window, the dolefulest you ever saw, and every now and then he'd fetch a groan.

A Special Providence 1995

There was nothing in the appointments of this simple meal to offend the most fastidious taste, and it was a sight to bring a smile to the dolefulest countenance, to see Rosalind and the magician sitting opposite to each other drinking tea.

Mr. Pat's Little Girl A Story of the Arden Foresters Mary Finley Leonard

The old gentleman he leaned his elbow on the window-sill, and his head on his hand, and looked out of the window, the dolefulest you ever saw, and every now and then he'd fetch a groan.

A Special Providence 1896

It has the poorest millionaires, the littlest great men, the lowest skyscrapers, the dolefulest pleasures of any town I ever saw.

Strictly business: more stories of the four million O. Henry 1886

Upon which Orchis said: 'Why, China Aster, you are the dolefulest creature.

The Confidence-Man 1857