Riddles can be difficult or simple as shown in these examples:

 "Three eyes have I, all in a row; when the red one opens, all freeze." The answer is
traffic light.
 "What animal walks on all fours in the morning, two in the afternoon and three in the
evening?" The answer is man, since he crawls as a child then walks and uses a cane
when he gets older.
 What does "Mill + Walk + Key=" The answer is Milwaukee.
 "What gets wetter and wetter the more it dries?" A towel of course.
 "No sooner spoken than broken. What is it?" It is silence.
 "I am weightless, but you can see me. Put me in a bucket, and I'll make it lighter. What
am I?" A hole.
 What is so fragile that when you say its name you break it? Silence.
 I have a tail, and I have a head, but i have no body. I am NOT a snake. What am I? A
coin.
 What falls, but does not break, and what breaks but does not fall? Night falls and day
breaks.
 You throw away the outside and cook the inside. Then you eat the outside and throw
away the inside. What did you eat? An ear of corn.
 I have holes in my top and bottom, my left and right, and in the middle. But I still hold
water. What am I? A sponge.
 What can run but never walks, has a mouth but never talks, has a head but never
weeps, has a bed but never sleeps? A river.
 I never was, am always to be,/No one ever saw me, nor ever will,/And yet I am the
confidence of all/To live and breathe on this terrestrial ball./What am I? Tomorrow.
 I am the black child of a white father, a wingless bird, flying even to the clouds of
heaven. I give birth to tears of mourning in pupils that meet me, even though there is no
cause for grief, and at once on my birth I am dissolved into air. What am I? Smoke.
 Pronounced as one letter,/And written with three,/Two letters there are,/And two only in
me./I'm double, I'm single,/I'm black, blue, and gray,/I'm read from both ends,/And the
same either way./What am I? An eye.
 A man is on a trip with a fox, a goose, and a sack of corn. He comes upon a stream
which he has to cross, and finds a tiny boat which he can use for the same. The
problem though, is that he can only take himself and either the fox, the goose, or the
corn across at a time. It is not possible for him to leave the fox alone with the goose or
the goose alone with the corn. How can he get all safely over the stream? Answer:
Take the goose over first and come back. Then take the fox over and bring the goose
back. Now take the corn over and come back alone to get the goose. Take the goose
over and the job is done!
 A boy was at a carnival and went to a booth where a man said to the boy, "If I write your
exact weight on this piece of paper then you have to give me $50, but if I cannot, I will
pay you $50." The boy looked around and saw no scale so he agrees, thinking no
matter what the carny writes he'll just say he weighs more or less. In the end the boy
ended up paying the man $50. How did the man win the bet? Answer: The man did
exactly as he said he would and wrote 'your exact weight' on the paper.
Who makes it, has no need of it.
Who buys it, has no use for it.
Who uses it can neither see nor feel it.
What is it? ANSWER: A coffin
What can travel around the world while staying in a corner? ANSWER: Stamp
I'm tall when I'm young and I'm short when I'm old. What am I? ANSWER: Candle
What has hands but cannot clap? ANSWER: Clock

You can drop me from the tallest building and I'll be fine, but if you drop me in water I die. What am
I? ANSWER: Paper

What has a head and a tail, but no body? ANSWER: Coin

What has an eye but cannot see? ANSWER: Needle
What gets wetter and wetter the more it dries? ANSWER: Towel
Paul's height is six feet, he's an assistant at a butcher's shop, and wears size 9 shoes. What does he
weigh? ANSWER: Meat
There was a green house. Inside the green house there was a white house. Inside the white house
there was a red house. Inside the red house there were lots of babies. What is it? ANSWER:
Watermelon

If you have me, you want to share me. If you share me, you haven't got me. What am I? ANSWER:
Secret

What is as light as a feather, but even the world's strongest man couldn't hold it for more than a
minute? ANSWER: His Breath

In "The Hobbit" by J. R. R. Tolkien, there are several hard riddles that Gollum and Bilbo ask each
other.
Alive without breath,
As cold as death;
Never thirsty, ever drinking,
All in mail never clinking. ANSWER: Fish

We'll float like a butterfly, sting like a bee

And leave you suckers black and blue
Though when we're in action we usually bleed
That's who we are, that's what we do
We do it for kicks and we do it for thrills
When boredom makes you lose your mind
But mostly we do it to pay off the bills
We hope that you can read the sign
Now give us our headgear or give us a punch
So we can hang around with you
You'd best wear protection alongside our bunch
Although you might be called a prude ANSWER: Pen

First you jerk me by my ear

Then you kiss me on the lips.
You say I'm hot and hold me near,
Then laugh that I lack shapely hips.

Up and down your silly game

Your passion stirred already,
Whether mood be light or dark -
Just try to hold me steady! ANSWER: Mug of coffee

I'm the acrobat at your command,

Give me a turn, or put me on the stand.
I'm the sentinel, doorman you need,
Give me a go, a go-ahead from me.

Hit me, poke me, nail me in your wake,

Without my flips, weak knees would quake.
I live in one state and travel to another,
Sunny side up or fumble in the other. ANSWER: Light switch

Five-walled open house

Shut my door and make it four.
I know exactly who you are,
Where you sleep, friends you keep.
A loyal soldier out on tour
I take my leaves overseas.
So pin the gold upon my breast,
Give me orders crossing borders. ANSWER: Envelop
Alive without breath,
As cold as death;
Never thirsty, ever drinking,
All in mail never clinking. ANSWER: Fish

Voiceless it cries,
Wingless flutters,
Toothless bites,
Mouthless mutters. ANSWER: Wind

What has roots as nobody sees,

Is taller than trees.
Up, up, up it goes,
And yet never grows? ANSWER: Mountain

We'll float like a butterfly, sting like a bee

And leave you suckers black and blue
Though when we're in action we usually bleed
That's who we are, that's what we do
We do it for kicks and we do it for thrills
When boredom makes you lose your mind
But mostly we do it to pay off the bills
We hope that you can read the sign
Now give us our headgear or give us a punch
So we can hang around with you
You'd best wear protection alongside our bunch
Although you might be called a prude ANSWER: Pen

A blustery wind blows over the bay

I hoist up my sails, I'm off on my way
Hoping to find, for the sake of my bands
A village to pillage in neighboring lands
I barge in the house
I drink all their wine
(Why, they hardly even seem like they mind!)
When business is done, I bolt out the door
Picking up more than I'm bargaining for
In port once again, my comrades all glance
And they all take note of my singing and dance
We're off to win GOLD!
We're leaving the bay
Harpooning whoever might stand in our way! ANSWER: Honeybee

A metal tube quite long and thin

My function seems surreal
Along my body coming in
I'm bringing quite a reel
Just cast me out into the waves
And leave me standing tall
I'll bring in catches that you crave
Unless I'm foiled by squalls
To find the perfect spot, explore
Shun ghosts, avoid the snow
It's best if you can monitor
What's going on below
I'll try to grab you with a hook
And lines that hold you tight
Designed to draw a longing look
Be careful should you bite ANSWER: TV Antenna

My buddies and I were inseparable mates

Til one by one were we split
My teacher, she gave me a smack on the pate
And off in the corner I sit

Admittedly still I'm not hitting the books

Though now I'm hugging a tree
I guess in the end it's not bad as it looks
I went from a C to a B ANSWER: Staple

I'd grab ahold of all I can

Relentless in my spree
Amidst the crimes I hung a man
And then the man hung me
I met some more of my own kind
We really got along
In open hid where none could find
Except the dead and gone ANSWER: Spider Web

Heaven sent with company

Clad in cloaks of four or three
Straight and narrow I'll not be
Thus my fate is cast
Sawn asunder as you're fain
In coffin uninterred lie slain
'neath ice with blood-stained ball and chain
Gouged until the last ANSWER: Banana

Entombed alive yet I survived

To glimpse once again at the sun
But legs to ground are shackled down
Curtailing all efforts to run
In body lies a dozen knives
My crown's sure to split and to smell
A robber's spear flew by my ear
Be thankful this ended so well ANSWER: Rose

As we face off, the white and black

I stand beside my twin
See sunbeams fall through patterned cracks
That lie above this den
Of diamond, sir, my heart's composed
It makes me who I am
Across that heart I keep exposed
The mark of Superman
If in the end our paths should meet
Then head o'er heels let's go
Should safeguards fail, there's no retreat
As I bring forth the snow ANSWER: Saltshaker

Bedecked in flowing robes

Assuming my humble station
I draw the curious globes
And strive to enlighten my patron
The task I've taken up
Providing you with protection
Unlike my peers corrupt
Distorting your sound perception
I shall not be long winded
Unless I am cast away
Results might be quite splendid
Or varying day by day
The prudent give me praise
The slovenly fools, rejection
For after several days
They only see imperfection ANSWER: Window

Snow has fallen to the ground

Still my lawn is clear
Lifeblood flowing all around
Doesn't wander here
Spring and Summer, nearly drown
Watering the lawn
Whether grass is green or brown
I will make it strong
When the days are hot as hell
Shade the sun above
Scorching not the quiet well
Where they fell in love ANSWER: An eye

First you jerk me by my ear

Then you kiss me on the lips.
You say I'm hot and hold me near,
Then laugh that I lack shapely hips.

Up and down your silly game

Your passion stirred already,
Whether mood be light or dark -
Just try to hold me steady! ANSWER: Mug of coffee

I'm the end that brings the end

I'm the one that hides.
Shackles gird me waist to toe
Sealed in tower I.
Ever tasked to make amends,
Slowly here I die.
My stricken foe you'll never know
His death is met with sigh. ANSWER: An eraser

I'm the acrobat at your command,

Give me a turn, or put me on the stand.
I'm the sentinel, doorman you need,
Give me a go, a go-ahead from me.

Hit me, poke me, nail me in your wake,

Without my flips, weak knees would quake.
I live in one state and travel to another,
Sunny side up or fumble in the other. ANSWER: Light switch

Five-walled open house

Shut my door and make it four.
I know exactly who you are,
Where you sleep, friends you keep.
A loyal soldier out on tour
I take my leaves overseas.
So pin the gold upon my breast,
Give me orders crossing borders. ANSWER: Envelop

Soldiers march all in a row

Through field, the part they play they know.
Soldiers black, soldiers tall
Across the fruited plain they crawl.
Grinning wide, standing firm,
Your ego safe they will confirm.
Scrape the dead, part the waves
They will not break, these soldiers brave. ANSWER: Comb

Treasure waits beyond the reach

gold within a hold,
remnants of the dead are stitched
to keep the living whole.
Broken bones among the weeds
scattered 'round and round,
where untouched gems wait silently
o'er blades upon the ground. ANSWER: Bird’s Nest

Stabbed and tied, have never died

Old as old can be,
Push me to the moral ends
I'm all for modesty.
Often lost and all alone
Find me without teeth,
The holes I bear with pride I wear
Security in my reach. Answer: Button

I rank higher than the privates,

Commander of the Line,
The uniform my noble goal
Security 'cross time.
Underway and under knots
My medal borne with pride,
Within my grasp a flag, sans mast
All noblemen would fly. ANSWER: Tie clip

Two girls were born to the same mother, on the same day, at the same time, in the same month and
year and yet they're not twins.
How can this be? ANSWER: The two babies are two of a set of triplets.

A girl who was just learning to drive went down a one-way street in the wrong direction, but didn't
break the law.
How come? ANSWER: She was walking

There was a man one night. He started to run straight forward. Then he turned left.
Soon after, he turned left again. Then he started running towards his home. When he
got home there were 2 masked men waiting for him. Who were they?
Answer: The man running was a baseball player. The 2 masked men were the catcher
and the umpire.
Fred owns a pet store. He puts one canary per cage, but has one bird too many. If he
puts two canaries in each cage, he has one cage too many. How many cages and
canaries does he have?
Answer: Fred has 3 cages and 4 canaries.
Two planes take off at the same exact moment. They are flying across the Atlantic.
One leaves New York and is flying to Paris at 500 miles per hour. The other leaves
Paris and is flying to New York at just 450 miles per hour. Which one will be closer
to Paris when they meet?
Answer: They will both be the same distance from Paris when they meet!

What walks on four legs in the morning, two legs at noon, and three legs in the
evening? Answer: "Man, who as a baby crawls on four legs, then walks on two
legs as an adult and in old age walks with a cane as his third leg."

In The Goblet of Fire, Harry Potter also has to face a sphinx in the tri-wizard
tournament. He has to solve this riddle of the sphinx:
'First think of the person who lives in disguise,
Who deals in secrets and tells naught but lies.
Next, tell me what's always the last thing to mend,
The middle of middle and end of the end?
And finally give me the sound often heard
During the search for a hard-to-find word.
Now string them together, and answer me this,
Which creature would you be unwilling to kiss?'
Answer: Spider

In The Hobbit, Bilbo Baggins and Gollum have a game of riddles. These are two
examples of riddles posed to Bilbo by Gollum:

"This thing all things devours;

Birds, beasts, trees, flowers;
Gnaws iron, bites steel;
Grinds hard stones to meal;
Slays king, ruins town,
And beats mountain down." Answer: Time

It cannot be seen, cannot be felt,

Cannot be heard, cannot be smelt.
It lies behind stars and under hills,
And empty holes it fills.
It comes first and follows after,
Ends life, kills laughter. Answer: Darkness

Riddle #1.
Until I am measured I am not known.
Yet how you miss me when I have flown.

Riddle #2.
If you drop me I'm sure to crack,
but give me a smile and I'll always smile back.

Riddle #3.
What always runs but never walks, often murmurs, never talks, has a bed but never sleeps, has a
mouth but never eats?

Riddle #4.
It's red, blue, purple and green.
No one can reach it, not even the queen.
Riddle #5.
I am the beginning of the end, and the end of time and space.
I am essential to creation, and I surround every place.

Riddle #6.
The one who makes it always sells it.
The one who buys it never uses it.
The one who uses it never knows he's using it.

Riddle #7.
What's black when you get it, red when you use it, and white when you're done with it?

Riddle #8.
Each morning I appear to lie at your feet.
All day I will follow no matter how fast you run, yet I nearly perish in the midday sun.

Riddle #9.
My life can be measured in hours.
I serve by being devoured.
Thin, I am quick. Fat, I am slow.
Wind is my foe.

Riddle #10.
You've heard me before, yet you hear me again,
Then I die 'til you call me again.

Riddle #11.
What does man love more than life,
Fear more than death or mortal strife.
What the poor have, the rich require,
and what contented men desire.
What the miser spends and the spendthrift saves,
And all men carry to their graves?

Riddle #12.
Three lives have I.
Gentle enough to soothe the skin,
Light enough to caress the sky,
Hard enough to crack rocks.

Riddle #13.
At the sound of me, men may dream or stamp their feet.
At the sound of me, women may laugh or sometimes weep.

Riddle #14.
I build up castles, I tear down mountains.
I make some men blind, I help others to see.

Riddle #15.
Reaching stiffly for the sky, I bare my fingers when it's cold.
In warmth I wear an emerald glove, and in between I dress in gold.

Riddle #16.
Whoever makes it, tells it not.
Whoever takes it, knows it not.
Whoever knows it, wants it not.

Riddle #17.
You saw me where I never was and where I could not be. And yet within that very place, my
face you often see.

Riddle #18.
Say my name and I disappear.

Riddle #19.
I drift forever with the current down these long canals they've made.
Tame, yet wild, I run elusive, multitasking to your aid.
Before I came, the world was darker. Colder, sometimes, rougher, true.
But though I might make living easy, I'm good at killing people too.

Riddle #20.
I am always hungry and will die if not fed, whatever I touch will soon turn red.

Answers:
Riddle #1. Time
Riddle #2. Mirror
Riddle #3. River
Riddle #4. Rainbow
Riddle #5. The letter "E"
Riddle #6. Coffin
Riddle #7. Charcoal
Riddle #8. Shadow
Riddle #9. CandleS
Riddle #10. Echo
Riddle #11. Nothing
Riddle #12. Water
Riddle #13. Music
Riddle #14. Sand
Riddle #15. Tree
Riddle #16. Counterfeit money
Riddle #17. Reflection
Riddle #18. Silence
Riddle #19. Electricity
Riddle #20. Fire