A betting hint is a TIP, though, and who has TIP in their name?

Ah! TIPTOE, the observant and philosophical fox in Book One. :D

And over we go ...

Y'know, he always has sounded like a refugee from Narnia. Proof, perhaps, of the old theory that the east-facing Narnia map and the west-facing Middle-earth map are supposed to back onto each other, making 'The Magician's Nephew' the canonical origin of Men in Arda? Further evidence is found in the fact that only a little fiddling lets you line the End of Narnia nicely with the Fall of Numenor and the Change of the World...

Anyway, no, and it's not a hint (or tip) to a gambler.

hS

For a couple of pins, says Troll, and grins ... is the Troll gambling 2 pins?

Is it Troll, or the Tom of the same song?

It is not. This is a named character, who is specifically noted to be unmarried (unlike the rest of the three (I SAID FOUR)).

hS

For some reason, it reminds me of the certain group of four, but only one of those is unmarried, and they're the answer to another clue.

Shortened road could be 'ROD', and Pin - Fin, so the answer could be Finrod.

What, Frodo? This is not an LotR clue.

Nope - the road isn't short (and the troll's pins aren't relevant either).

Some thoughts:

-What is a road made of?
-What hint might a gambler (accidentally) give?
-'a misspelled Hobbit' does not refer to a specific hobbit.

hS

I thought of one of the TAR-s, but then thought that too much of a leap from 'road.'

TAR-TELPERIEN.

Perian misspelt. One of three, but should have been four, (damn you, Ar-Pharazon!) ruling queens of Numenor. I guess she was the only unmarried one of the four.

A gambler might 'tell' someone a hint by accident?

Nothing is too much of a leap! :D:D:D

(This is not actually a statement of gameplay philosophy, fear not.)

In games like poker, the involuntary habits which reveal what a player is thinking - such as tapping their fingers on the table, or blinking rapidly - are known as tells.

URWEN - An ancient city (now? then? Start huffing less) with an older and sadder name.
NIENNA - An endless Elvish gift: one German backwards cries.
CELEBRIMBOR - Retro voting is full to the-- but dull, topped and tailed by an artisan.
OAKENSHIELD - Not ash, and not the dead one, but good for protecting a wandering king.
MITHRANDIR - Lisp, Miss, and dispose (of) fire/a dwarf back to one wearing blue (blue?).
MAURA - Mother, you are a-- no, cut that down, wounded one.
IRIME - I rhyme! Or is that frost? Hang out in Hithlum and you'll see (probably).
TAR-TELPERIEN - A road, a short gambler's hint, and a misspelled Hobbit for the second of three (FOUR!).
THEODRED - If you don't know Latin, fear God and guard the ford.
EARNUR - Make lots of money! Say "He know(s) you," and ride to the city.
DAERON - If Weasley was a werewolf, he might live a wolf, but he would... play music!

Theme: Unmarried characters

Over to you, I think, Pervinca.

hS

Another great password, Huinesoron!

Here we go again, then:

1. One who loves the dark side swallows double zero, two directions and a note here?
2. Crooked cross. Destruction. And here we are.
3. Circle that draws lines?
4. Charged component in great turmoil for her.
5. Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
6. In him, a palindrome girl meets a sailor.
7. See the back of the article here, mon ami.
8. He’d be a palindrome, but a note becomes a point.
9. Thank you, trumpet, for perplexing him!
10. He really is almost human!
11. Mix female-born herb for him.
12. Beleg returns, with noted change and edge. Denethor’s little son completes him.
13. Call, master, and see him.
14. Den inside undisclosed igloos? Yes, initially. There they are!
15. This time, a glaring palindrome!
16. Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

12. Celebrimbor?

Indeed!
 

1. One who loves the dark side swallows double zero, two directions and a note here?
2. Crooked cross. Destruction. And here we are.
3. Circle that draws lines?
4. Charged component in great turmoil for her.
5. Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
6. In him, a palindrome girl meets a sailor.
7. See the back of the article here, mon ami.
8. He’d be a palindrome, but a note becomes a point.
9. Thank you, trumpet, for perplexing him!
10. He really is almost human!
11. Mix female-born herb for him.
CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
13. Call, master, and see him.
14. Den inside undisclosed igloos? Yes, initially. There they are!
15. This time, a glaring palindrome!
16. Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

10. Huan

1. One who loves the dark side swallows double zero, two directions and a note here?
2. Crooked cross. Destruction. And here we are.
3. Circle that draws lines?
4. Charged component in great turmoil for her.
5. Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
6. In him, a palindrome girl meets a sailor.
7. See the back of the article here, mon ami.
8. He’d be a palindrome, but a note becomes a point.
9. Thank you, trumpet, for perplexing him!
HUAN: He really is almost human!
11. Mix female-born herb for him.
CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
13. Call, master, and see him.
14. Den inside undisclosed igloos? Yes, initially. There they are!
15. This time, a glaring palindrome!
16. Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

#13 seems to point to RING-LORD, but I'm not sure Tolkien uses that term.

Actually, #3 seems like it might be a 'ring' clue as well, but I'm not sure what.

hS

1. One who loves the dark side swallows double zero, two directions and a note here?
2. Crooked cross. Destruction. And here we are.
3. Circle that draws lines?
4. Charged component in great turmoil for her.
5. Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
6. In him, a palindrome girl meets a sailor.
7. See the back of the article here, mon ami.
8. He’d be a palindrome, but a note becomes a point.
9. Thank you, trumpet, for perplexing him!
HUAN: He really is almost human!
11. Mix female-born herb for him.
CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
RINGLORD: Call, master, and see him.
14. Den inside undisclosed igloos? Yes, initially. There they are!
15. This time, a glaring palindrome!
16. Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

Your hunch about Clue 3 is right, too.

... it's RULING RING, isn't it?

#9: A long shot, but this could be TANTA (Ta'n'Ta) HORNBLOWER. I suspect 'perplexing' points at an anagram, though.

hS

Well Done!
 

1. One who loves the dark side swallows double zero, two directions and a note here?
2. Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
4. Charged component in great turmoil for her.
5. Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
6. In him, a palindrome girl meets a sailor.
7. See the back of the article here, mon ami.
8. He’d be a palindrome, but a note becomes a point.
9. Thank you, trumpet, for perplexing him!
HUAN: He really is almost human!
11. Mix female-born herb for him.
CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
RINGLORD: Call, master, and see him.
14. Den inside undisclosed igloos? Yes, initially. There they are!
15. This time, a glaring palindrome!
16. Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

You need a different synonym for 'clarion.'

I feel bad for you for doing this, but I'm going to take the clue: TAR-CALION (Ta clarion) for #9.

Which definitely puts a Sauron theme of some kind on the whole password.

hS

I love the Huan clue. It is so punny! :D

6. ANNATAR

1. One who loves the dark side swallows double zero, two directions and a note here?
2. Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
4. Charged component in great turmoil for her.
5. Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
7. See the back of the article here, mon ami.
8. He’d be a palindrome, but a note becomes a point.
TAR-CALION: Thank you, trumpet, for perplexing him!
HUAN: He really is almost human!
11. Mix female-born herb for him.
CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
RINGLORD: Call, master, and see him.
14. Den inside undisclosed igloos? Yes, initially. There they are!
15. This time, a glaring palindrome!
16. Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

Hoist with me own synonym, to be sure! ;)

Allow me to say that I hate that guy. Hate him.

Interesting info: His name might stem from the elvish 'arpho', which means 'seizer'.

GORTHAUR THE CRUEL for password?

2. ORODRUIN, from O...RUIN?

G: One who loves the dark side swallows double zero, two directions and a note here?
ORODRUIN: Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
T: Charged component in great turmoil for her.
H: Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
U: See the back of the article here, mon ami.
R: He’d be a palindrome, but a note becomes a point.

TAR-CALION: Thank you, trumpet, for perplexing him!
HUAN: He really is almost human!
E: Mix female-born herb for him.

CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
RINGLORD: Call, master, and see him.
U: Den inside undisclosed igloos? Yes, initially. There they are!
E: This time, a glaring palindrome!
L: Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

ORODRUIN is ROOD made crooked, plus RUIN.

UDUN for the first U, because un + du, both French articles?

And ULAIRI for the other U: U(ndisclosed) + LAIR + I(gloos)

For 1 I kept thinking the dark side lover had to be something like Sith... But working backwards, it becomes GOTH + OO + RR + G = GORGOROTH

GORGOROTH: One who loves the dark side swallows double zero, two directions and a note here?
ORODRUIN: Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
T: Charged component in great turmoil for her.
H: Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
UDUN: See the back of the article here, mon ami.
R: He’d be a palindrome, but a note becomes a point.

TAR-CALION: Thank you, trumpet, for perplexing him!
HUAN: He really is almost human!
E: Mix female-born herb for him.

CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him.
RINGLORD: Call, master, and see him.
ULAIRI: Den inside undisclosed igloos? Yes, initially. There they are!
E: This time, a glaring palindrome!
L: Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

Good work!

UDUN is DU, the French for 'of the,' backwards, then the article, UN.

Is the R RODNOR, aka Gil-Galad of disputed parentage? With the second 'D' that would make it a palindrome turning into N which... has points, I guess?

And based purely on 'her', and the relatively low number of women who've run into Sauron: is T TINUVIEL? (I really wanted to find an anagram of 'battery', or maybe 'capacitor', but... ;))

hS

The image of the Faithful coming up with snarky folk etymologies for the King's Men's names amuses me immensely.

There's a Primitive Elvish rood 'Arga', dread, dreadful which could be similarly interpreted as the source of Ar-Gimilzor. ;)

hS

GORGOROTH: One who loves the dark side swallows double zero, two directions and a note here?
ORODRUIN: Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
TINUVIEL: Charged component in great turmoil for her. (Bested by her)
H: Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
UDUN: See the back of the article here, mon ami.
RODNOR: He’d be a palindrome, but a note becomes a point. (His bane)

TAR-CALION: Thank you, trumpet, for perplexing him! (Deceived him)
HUAN: He really is almost human! (Bested him)
E: Mix female-born herb for him.

CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him. (Had him executed)
RINGLORD: Call, master, and see him.
ULAIRI: Den inside undisclosed igloos? Yes, initially. There they are!
E: This time, a glaring palindrome!
L: Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

I think TINUVIEL must have been LIVE UNIT.

Oh! Is the final E EYE?

hS

GORGOROTH: One who loves the dark side swallows double zero, two directions and a note here?
ORODRUIN: Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
TINUVIEL: Charged component in great turmoil for her. (Bested by her)
H: Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
UDUN: See the back of the article here, mon ami.
RODNOR: He’d be a palindrome, but a note becomes a point. (His bane)

TAR-CALION: Thank you, trumpet, for perplexing him! (Deceived him)
HUAN: He really is almost human! (Bested him)
E: Mix female-born herb for him.

CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him. (Had him executed)
RINGLORD: Call, master, and see him.
ULAIRI: Den inside undisclosed igloos? Yes, initially. There they are!
EYE: This time, a glaring palindrome!
L: Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

It is. And the 'Shakespearean' word for snag/problem in the L clue can be found in the most famous of Hamlet's soliloquies.

I found the word, but Lugburz is the only thing that makes sense given the word and the theme. But I don't see how LUGZ = HMNB Devonport?

GORGOROTH: One who loves the dark side swallows double zero, two directions and a note here?
ORODRUIN: Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
TINUVIEL: Charged component in great turmoil for her. (Bested by her)
H: Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
UDUN: See the back of the article here, mon ami.
RODNOR: He’d be a palindrome, but a note becomes a point. (His bane)

TAR-CALION: Thank you, trumpet, for perplexing him! (Deceived him)
HUAN: He really is almost human! (Bested him)
E: Mix female-born herb for him.

CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him. (Had him executed)
RINGLORD: Call, master, and see him.
ULAIRI: Den inside undisclosed igloos? Yes, initially. There they are!
EYE: This time, a glaring palindrome!
LUGBURZ: Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

For some reason - and I have no idea why - the barracks at HMNB Devonport have the nickname GUZ. I became aware of a place/thing called GUZ when I read a Charles Causley poem called 'Song of the Dying Gunner,' which has a line that goes 'Farewell Aggie Weston, the barracks at Guz.'

'To sleep, perchance to dream - ay, there's the RUB.' ('Mirror' it).

And 'well-directed start' tells you to put a direction, (L, as it happens), at the beginning.

...

Two to go!

I already know about rub, so you didn't have to explain that too (unless of course, you explained for the benefit of everyone else), but I see. :)

Noooo. Pervinca, you're killing me. :D



For the H, based on "them" it likely refers to a group of people - so maybe HARADRIM? Has HIM + 2xA + D (and RR somehow makes 2 liquids?)


PS: Huey, a "point" is a compass point - in this case N for North.

GORGOROTH: One who loves the dark side swallows double zero, two directions and a note here?
ORODRUIN: Crooked cross. Destruction. And here we are.
RULING RING: Circle that draws lines?
TINUVIEL: Charged component in great turmoil for her. (Bested by her)
HARADRIM: Two articles, two liquids, a note and a pronoun. Mix them up to reveal them.
ANNATAR: In him, a palindrome girl meets a sailor.
UDUN: See the back of the article here, mon ami.
RODNOR: He’d be a palindrome, but a note becomes a point. (His bane)

TAR-CALION: Thank you, trumpet, for perplexing him! (Deceived him)
HUAN: He really is almost human! (Bested him)
E: Mix female-born herb for him.

CELEBRIMBOR: Beleg returns, with noted change and edge. Denethor’s little son completes him. (Had him executed)
RINGLORD: Call, master, and see him.
ULAIRI: Den inside undisclosed igloos? Yes, initially. There they are!
EYE: This time, a glaring palindrome!
LUGBURZ: Here’s a well-directed start. A Shakespearean snag is mirrored. And HMNB Devonport is sprinkled around.

Perfectly correct, Galadriel. :)

Which clue were you referring to with the compass point - is it in another recent password?

A CLUE for the one remaining unsolved answer: what's the female form of a term that means 'born,' that you tend to find on firms, passports, etc? ;)

Well, the only term I could find is 'issued', but I can't find female term for that.

It's a French term.

Naissance?