See Also: DEJECTION, EMOTIONS, GLOOM

1. As full of sorrow as the sea of sands —William Shakespeare
2. Could feel it [the sadness] pierce him like a foreign body in his heart —Amos Oz
3. Crest-fallen as a dried pear —William Shakespeare
4. Crest-fallen as a spy who had been caught by a thief —Victor Hugo
5. Depressing as the last day of fishing —Robert Traver
6. A feeling of sadness that is not akin to pain, resembles sorrow only as the mist resembles rain —Henry Wadsworth Longfellow
7. (Scarlett) felt bereft, as though she had sold one of her children —Margaret Mitchell

   The sadness which inspired the comparison was that experienced by the heroine of Gone With the Wind when she sold her lumber business.

8. Felt melancholy grip him, like a pain in the heart —Mary McCarthy
9. (I felt depressed,) filled to the neck with sadness like a carafe with bad wine —T. Coraghessan Boyle
10. His heart throbbed like a bruise in the sigh —Norman Mailer
11. His heart would sink down to his bowels like lead —Thomas Wolfe
12. Looked and acted like a man who had just driven home from a couple of heart-rending funerals —George Ade

    See Also: FACIAL EXPRESSIONS, SERIOUS

13. Melancholy as a discarded statesman —William Mountford
14. Melancholy as a fiddle with one string —Thomas Holcroft
15. My heart is within me as an ash in the fire —Algernon Charles Swinburne
16. My heart was as lead —Jack London
17. Pathetic as all final efforts —Alice McDermott
18. Pathetic as an autumn leaf —George Moore
19. (A low call,) plaintive as a shepherd calling, to sheep who need no strident invocation —Arthur A. Cohen
20. Sad as an eagle without wings, sad as a violin with only one string —Jean Rhys
21. Sad as night —William Shakespeare
22. Sad as professional mourners —F. Scott Fitzgerald
23. Sad as twilight —George Eliot
24. Saddening as a forest fire —Robert Traver
25. Sad like graveyards —Terry Bisson
26. Sad … like somebody who’s pilot light got blown out a long time ago —Susan Kelly
27. Sadness … gnawed like a rat at his mind —Roderic Jeffries
28. Sadness, like that inspired by a grave strain of music —Joseph Conrad
29. Sadness that, over the years, had gathered in his chest like matter in a clogged drain —Joyce Reiser Kornblatt
30. There would come, like water washing over a sunken buoy, the little knell of sadness —Hortense Calisher

Just as similes are used to give dramatic beginning to literary works, they can also be used to wind things up, as demonstrated by this final sentence from Calisher’s novel, Point of Departure.