13
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Be sure to keep watch,
a tough guy just walked in.
He's got a reputation in these backwards parts,
and he could deliver a real beating.
If there's a lady around, he'll just hold his cup.
I think, for the most part, he's just a mixed-up fool.

Each line matches the correct answer, but the title's irrelevant. None of the clues is literally applicable; it's a little more cryptic.

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  • 1
    $\begingroup$ If the clues where literally applicable, Sir Henry Morgan would have been a perfect fit :/ $\endgroup$ – Jean-François Savard Aug 11 '15 at 14:40
  • $\begingroup$ @Jean-FrançoisSavard Hah, not bad! Even ends up on the rum :P $\endgroup$ – Samthere Aug 11 '15 at 14:42
17
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The answer is

strap

Be sure to keep watch,

A watch strap

a tough guy just walked in.

As in a strapping lad

He's got a reputation in these backwards parts,

strap is parts backwards

and he could deliver a real beating.

To give someone the strap

If there's a lady around, he'll just hold his cup.

A bra strap, though possibly also works with jockstrap

I think, for the most part, he's just a mixed-up fool.

Anagram of sprat, though prat is more common these days, hence the "most part".

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  • $\begingroup$ hold his cup -> jockstrap $\endgroup$ – NeedAName Aug 11 '15 at 14:18
  • 2
    $\begingroup$ "If there's a lady around, he'll just hold his cup" could refer to a bra strap and a cup size. $\endgroup$ – Aggie Kidd Aug 11 '15 at 14:19
  • $\begingroup$ Thanks, @NeedAName, I edited jockstrap in within the 5 minutes :) $\endgroup$ – ClickRick Aug 11 '15 at 14:20
  • $\begingroup$ Excellent work! As Aggie mentions, I had intended line 5 as a bra, but jock strap works equally well. $\endgroup$ – Samthere Aug 11 '15 at 14:25
  • 4
    $\begingroup$ And here we present the only case ever where jock strap and bra work interchangeably. $\endgroup$ – corsiKa Aug 11 '15 at 22:38
13
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I take my chance with:

Jon Snow (from Game of Thrones)

Be sure to keep watch,

Jon works on the Night's Watch

a tough guy just walked in.

He is quite the tough guy beating wildings and white walkers

He's got a reputation in these backwards parts,

Reputation for being a bastard but also because he is a great fighter

and he could deliver a real beating.

He is a great fighter

If there's a lady around, he'll just hold his cup.

You are not allowed to sleep with women in the watch, so he'll just hold his cup...

I think, for the most part, he's just a mixed-up fool.

You could said that he is a mixed-up fool because he wants to help the wildings but he is from the night's watch.

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  • $\begingroup$ Nice guess and good application, but it's a bit more cryptic. I'll add a note to the main question. +1 $\endgroup$ – Samthere Aug 11 '15 at 13:26
  • 17
    $\begingroup$ You know nothin', TroyAndAbed! $\endgroup$ – CodeNewbie Aug 11 '15 at 13:38
  • 2
    $\begingroup$ TroyAndAbed knowing noooothing! $\endgroup$ – Telestia Aug 11 '15 at 16:35
2
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Sounds like a

cake

Be sure to keep watch,

Take care, don't drop it.

a tough guy just walked in.

I guess "tough" is a word that can be used to describe the consistence of cake.

He's got a reputation in these backwards parts,

Cake is said to be very tasty and ofc many people like it.

and he could deliver a real beating.

Thinking of films when people throw cakes at faces.

If there's a lady around, he'll just hold his cup.

Maybe some referrence to drinking coffee/tea etc,

I think, for the most part, he's just a mixed-up fool.

A cake is the result of mixing together ingredients.

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  • $\begingroup$ Good try, but most of the clues here feel pretty stretched, getting better towards the end. $\endgroup$ – Samthere Aug 11 '15 at 13:30
2
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Alcholol

Be sure to keep watch,

Dont drink too much

a tough guy just walked in.

Alcohol can be dangerous.

He's got a reputation in these backwards parts,

Not sure: after many drinks you forget parts of the day before and people have to tell you afterwards.

and he could deliver a real beating.

Hangovers suck

If there's a lady around, he'll just hold his cup.

?Ladys drink from cups guys from bottles?

I think, for the most part, he's just a mixed-up fool.

Alot of people mix alcohol.

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  • $\begingroup$ Maybe one can simply hit somebody's head with a bottle (of wine,...) :D $\endgroup$ – Avigrail Aug 11 '15 at 13:15
  • 2
    $\begingroup$ There's some good leads, especially with lines 3, 4 and 6! Unfortunately the others don't match as well and it's not the intended answer. Good try! $\endgroup$ – Samthere Aug 11 '15 at 13:28
  • $\begingroup$ @Samsthere whiskey was my original guess $\endgroup$ – Sven van den Boogaart Aug 11 '15 at 13:41
1
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I'm going to take a guess at:

Caitlyn Jenner, formerly known as Bruce Jenner

Be sure to keep watch, a tough guy just walked in.

College football player, and Olympic athlete

He's got a reputation in these backwards parts, and he could deliver a real beating.

Married a Kardashian, the surname being famous for their "backwards parts". Also won Gold in the Decathlon at the Olympics.

If there's a lady around, he'll just hold his cup. I think, for the most part, he's just a mixed-up fool.

Now he is the lady around, with his own "cups". Mixed-up in that he "dealt with gender dysphoria since youth", hence the gender transition.

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  • $\begingroup$ Interesting direction and a good attempt, but unfortunately it doesn't fall into place as well in the earlier parts. Nice try! $\endgroup$ – Samthere Aug 11 '15 at 14:30

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