11
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What does this list represent?

20 (e.g.)
20 (exactly)
20 (compared to 350)
20 (compared to 3)

20 (e.g.)
20 (when scored by the NY Giants in 1991)
20...21...22...23...
20 (when the last in this list)

Hint:

Result of rifle placed by oaf (7)

Hint 2:

Dude found in part of Guam? Why? (3)

Hint 3:

MST3K movie has Chet troubled in mill (8)

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  • 1
    $\begingroup$ Sorry are those numbers hinting at wordlength or its position on the list? $\endgroup$ – Prince Deepthinker Nov 18 '20 at 7:57
  • $\begingroup$ The hints are cryptic clues ended by the number of letters in the answer. $\endgroup$ – Exal Nov 18 '20 at 8:26
5
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Lot of credit to @Stiv for this who got the final answer when I was turning down a large rabbit hole (see edits for a laugh).

Logic at the bottom for the starting point, though I think it was almost impossible before the hints.

These are all relating to:

The song lyrics for Heartaches By The Number, specifically the last word in each line (assuming you're not looking at a version that combines pairs of lines)

20 (e.g.)

Number

20 (exactly)

Score

20 (compared to 350)

Less

20 (compared to 3)

More

20 (e.g.)

Number

20 (when scored by the NY Giants in 1991)

Win (this really threw me - knowing nothing about American Football, googling it showed me the Giants had a mediocre 1991 season after winning the previous Super Bowl. Didn't realise it had been in January

20...21...22...23...

Counting

20 (when the last in this list)

End

Logic for identifying the connection:

Hint #2

Dude found in part of GUam? WhY? (3) => GUY

Hint #3

MST3K movie has Chet troubled in mill (8) => MITCHELL (only possible anagram of chet inside mill, plus on a list of MST3K movies)

So that gives us

Guy Mitchell, for which the only reference I can see is [this singer]. Can't see how any of his songs listed are relevant to the clues though3.

However, having now solved Hint #1

Result of rifle placed by oaf (7) => FALLOUT (FAL + LOUT)

It turns out that:

Heartaches By the Number was a Guy Mitchell song featured in Fallout: New Vegas. So presumably all the clues refer either to the game, or to heartaches, or troubles

Puzzle title:

The second half of the first line of Heartaches By the Number is "...troubles by the score". 20 = a score, title is literally "troubles" by(beside) a score

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  • $\begingroup$ You might be on to something here - that song has the lyric rot13("Gebhoyrf ol gur fpber") and many others like it - since that has a numeric connotation to '20' that's a very strong connection... $\endgroup$ – Stiv Nov 18 '20 at 17:14
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    $\begingroup$ Ha! Had just added that, snap! $\endgroup$ – Mohirl Nov 18 '20 at 17:17
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    $\begingroup$ I've got it! But you made the breakthrough so I think you should post it: each line is rot13(n pyhr gb gur ynfg jbeq va gur svefg 8 yvarf bs gur fbat: ahzore, fpber, yrff, zber, ahzore, jva, pbhagvat, raq) $\endgroup$ – Stiv Nov 18 '20 at 17:27
  • $\begingroup$ Also, this is the relevant match for the 1991 reference. $\endgroup$ – Stiv Nov 18 '20 at 17:34
  • $\begingroup$ Hey, thanks a million. Added the answers in, I was heading the wring way. That one you linked had really thrown me - googling it put me a year out $\endgroup$ – Mohirl Nov 18 '20 at 17:42

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