Etymology
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cheerless (adj.)

"devoid of comfort, without joy," 1570s, from cheer (n.) + -less. Related: Cheerlessly; cheerlessness.

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gloom (n.)

1590s, originally Scottish, "a sullen look," probably from gloom (v.) "look sullen or displeased" (late 14c., gloumen), of unknown origin; perhaps from an unrecorded Old English verb or from a Scandinavian source (compare Norwegian dialectal glome "to stare somberly"), or from Middle Low German glum "turbid," Dutch gluren "to leer." Not considered to be related to Old English glom "twilight" (see gloaming).

Sense of "darkness, obscurity" is first recorded 1629 in Milton's poetry; that of "melancholy, dejection, cloudiness or cheerless heaviness of mind" is from 1744; but gloomy with a corresponding sense is attested from 1580s.

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bleak (adj.)

c. 1300, bleik, "pale, pallid," from Old Norse bleikr "pale, whitish, blond," from Proto-Germanic *blaika- "shining, white" (source also of Old Saxon blek "pale, shining," Dutch bleek, Old High German bleih, German bleich), from PIE root *bhel- (1) "to shine, flash, burn," also "shining white."

The original English sense is obsolete; the meaning "bare, windswept" is from 1530s; the figurative sense of "cheerless" is from c. 1719. The same Germanic root produced Middle English blake "pale" (Old English blac), but this fell from use, probably from confusion with blæc "black" (the surname Blake can mean either "one of pale complexion" or "one of dark complexion"). Bleak has survived, not in the "pale" sense, but meaning only "bare, barren." Related: Bleakly; bleakness.

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dismal (adj.)
Origin and meaning of dismal

c. 1400, "unlucky, inauspicious," in dismal day, earlier as a noun, in the dismal (c. 1300) "in days of misfortune or disaster, under inauspicious circumstances, at an unlucky time," from Anglo-French dismal (mid-13c.), apparently from Old French (li) dis mals "(the) bad days," from Medieval Latin dies mali "evil or unlucky days" (also called dies Ægyptiaci), from Latin dies "days" (from PIE root *dyeu- "to shine") + mali, plural of malus "bad" (from PIE root *mel- (3) "false, bad, wrong").

Through the Middle Ages, calendars marked as unlucky two days of each month (Jan. 1, 25; Feb. 4, 26; March 1, 28; April 10, 20; May 3, 25; June 10, 16; July 13, 22; Aug. 1, 30; Sept. 3, 21; Oct. 3, 22; Nov. 5, 28; Dec. 7, 22), supposedly based on the ancient calculations of Egyptian astrologers.

By 1580s the English word had been extended to "gloomy, dreary, cheerless," and was used to describe physical surroundings, sounds, or anything else felt as tending to depress the spirits. In North America, it was the name given along the seacoast and sounds around North Carolina to tracts of swampy land and dead trees (1763). The dismal science (1849) was Carlyle's name for "political economics." Related: Dismally.

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dark (adj.)
Origin and meaning of dark

Middle English derk, later dark, from Old English deorc "without light, lacking light or brightness (especially at night), obscure, gloomy;" figuratively "sad, cheerless; sinister, wicked," from Proto-Germanic *derkaz (source also of Old High German tarchanjan "to hide, conceal"), which is of uncertain etymology. For vowel change, see marsh.

Application to colors, "not radiating or reflecting much light," is from late 14c. Of complexion, "not fair," from early 14c. Figurative sense of "obscure, not easily understood" is from early 13c.; that of "sullen, sad" is from 1590s. Meaning "concealed, secret" is from late 14c. Dark Continent "Africa" (1828) combines several figurative senses (earliest references are in missionary publications). Theater slang for "closed" is from 1916.

Dark Ages "benighted time in history, period of ignorance" is attested by 1739; the specific focus on the centuries of the early Middle Ages in Europe, from the fall of Rome to the revival of secular literature, is from 1830s, from dark in a sense of "characterized by ignorance, backward in learning, void of intellectual light" (late 14c.). 

Dark horse "competitor for honors or office about whom nothing certain is known, or whose identity is at first concealed," especially, in U.S., politics, "one who is unexpectedly brought forward as a candidate in a convention," 1842, is an image from horse racing, of horses whose performances or capabilities are not generally known, in which dark is used in its figurative sense of "unknown."

Moonraker is called a "dark horse"; that is neither his sire nor dam is known. ["Pierce Egan's Book of Sports," London, 1832] 
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