Sorry, no online dictionaries contain the exact phrase most depressing.
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Reverse dictionary results:
1. worse
2. worst
3. nadir
4. bad
5. bleak
6. deplorable
7. disgraceful
8. dismal
9. gloomy
10. grim
11. lamentable
12. pathetic
13. pitiful
14. regrettable
15. sad
16. tragic
17. unfortunate
18. hole
19. pit
20. gruesome
21. sombre
22. touch
23. touched
24. typing
25. black
26. depressed
27. fark
28. blue
29. chill
30. chills
31. cold
32. dump
33. pitting
34. shadow
35. sorry
36. oppressive
37. blueprint
38. dingy
39. jack
40. jacked

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