Sesame Street/Funny

This early skit where Kermit speaks about the letter B. Then Cookie Monster (unnamed at the time) emerges and starts consuming the letter piece by piece. The B turns into an R, then a P, to an F, to a I? A small L? Number 1?, so Kermit tries to keep up with the letter change.
- And don't forget that even though Kermit can't at the moment think of any words for the letter "P", in reference to the letter "F" is: "Now the letter 'F' starts a number of words I can think of."
- Also in the longer version of this sketch (if you can find it) is Kermit's humorous rant about the future Cookie Monster's manners which prompts the monster to come back and apologize... with a big, slobbering, monster kiss on Kermit's face followed by Kermit's patent "Yeesh" face.
In an early episode, the aftermath of Kermit's rectangle lecture visited by Cookie Monster. "It's a wreck, and a it's a tangle! Ahahahaha."
A hilarious Take That at those who believe in the Veggie Monster rumors and the media in general
After Grover pesters Kermit too many times to purchase earmuffs, Kermit confesses he doesn't have any ears.
The skits that have dog-headed humans acting out various mundane activities:
- Mechanic
- Home Cooking, made funnier with the right cook's subpar discipline.
- Barber
"Little Red Riding Cookie. Particularly the fact that Cookie Monster views it as a melodrama masterpiece. Not to mention how hilarious the Grandma is.
Don Music banging his head on the piano while songwriting with Kermit the Frog.
Bert teaches his pigeon to play checkers. Ernie is suitably impressed, and says that a pigeon that plays checkers has to be the smartest pigeon in the whole world.

Bert: She's really not that smart, Ernie. [...] Out of ten games we've played... she's only beaten me twice.

Bert is It!
A crossover funny moment with The Daily Show: After Jon Stewart pointed out that Grover's harried restaurant customer looked just like Republican Party Chairman Michael Steele, they were able to get that Muppet (or at least a replica) as their own Muppet Michael Steele, responsible for some of the show's best moments.
The Sesame Muppets appearing on talk shows. They tend to get a little more PG-13 when there aren't kids watching.
- Elmo on Jimmy Fallon.
- Big Bird on Jimmy Kimmel.
- Cookie Monster on The Colbert Report.
  - "Me have crazy times in '70s and '80s."
  - *Pointing to Stephen's Peabody Award* "Is that cookie?"
  - At the end of that show, the Award mysteriously disappears as Cookie Monster wipes his lips...
The ending of Christmas Eve on Sesame Street. Big Bird (who spent the entire special worrying about how Santa would fit down the chimney) sputtering silently after Oscar asks him how the Easter Bunny is able to hide so many eggs in one night is priceless. Cue an "OSCAR!" from the humans.
"I am on a horse... Moo! ... cow." Not to mention everything before it.
In Christmas Eve on Sesame Street during a discussion of Santa Claus:

Kermit: Who knows more about Santa Claus than anybody?
Patty: The elves!
Big Bird: Uh, Mrs. Claus?
Patty: Macys!

The entirety of the classic sketch "The Magic Apple" from Sesame Street. Bob is narrating a book that is in turn being performed by Ernie and a couple of other muppets. Fourth-wall violations abound. But this sketch gets especially funny when they trot out a very reluctant Bert in drag, who had to play the part of the princess in the script because no one else was around to do so. "You look great, Bert. You're beautiful!"
The entire skit in which Bert and Ernie go fishing is a classic example of Sesame Street's brilliant humor, especially when Ernie's rather unorthodox method of catching fish proves to be far more successful than Bert's more traditional approach.
- "Heeeeree FISHY! FISHY! FISHY! FISHY! Heeeeeeeereeee FISHY! FISHY! FISHY! FISHY!"
Robert DeNiro teaches Elmo how to act. Hilarity and Surprises ensue. Oh, and he even gives a Shout-Out to some of his previous roles:

DeNiro: I can be a New York City taxi driver, an out-of-shape boxer, or a cabbage.

Forgetful Jones singing "Oklahoma" wrong (and Kermit's reaction each time).
Kermit's visit to the Wonderful World of T-Shirts.
Grover messing up with the pizza that Mr. Johnson ordered.
ABC Cookie Monster: A little girl sings the alphabet song with Kermit, but every so often, giggling hysterically, she replaces one of the letters with "Cookie Monster". Kermit's reactions are priceless. After the fourth time, Kermit says, "Next time Cookie Monster can do this with you. I'm leaving! Hmmmph!" and storms off. It becomes a Heartwarming Moment when the little girl immediately says, "I love you!" and Kermit comes back on: "I love you, too." And she kisses him.
Oscar was, on the day of Gabi's birth, the only one making regular contact with Luis. Oscar, doubting his honor as a grouch, refuses to tell a soul whether the baby has been born. Bob uses reverse psychology to assure Oscar that he is as grouchy as ever. It doesn't work. Pretty soon, David and Gordon are about ready to kill Oscar. Take a look at this!
Spider Monster: http://www.youtube.com/watch?v=aR1DdMeVqTw
Normally the martians are seen as Nightmare Fuel, and they are for Ernie, but...

Ernie: "Bert! BERT! The martians are here Bert! What'll we do Bert?!"
Bert: *completly deadpan* "Ask them if they want any oatmeal."

- and then the martians wiggle off to the kitchen to get some oatmeal.
The whole "Waiting for Elmo" skit, parodying, of all things, Waiting for Godot. Especially when the tree itself has enough of it and just leaves the set.
The crew of Cake Boss had a task to create a huge cake for Sesame Workshop's 40th anniversary of the show... where they met Cookie Monster. Buddy mentions to him that he bakes cakes......... and Cookie completely fanboys over him. When they ship the cake over to the studio again, they give Cookie a surprise- an ENORMOUS cake made to look like a cookie the size of a table! Cookie's reaction is priceless.
Kermit, Cookie Monster and the Mystery Box. It's performed masterfully and it is gut bustingly hilarious seeing Kermit lose his temper.
One episode from Season 37 has Cookie Monster doing his own version of "Elmo's World" called (naturally) "Cookie World". It's an Internal Homage that goes close to Self-Parody at some points.
Ernie has trouble sleeping, so he tries Counting Sheep, which is visualized to the audience. However, their bleating is so loud that Bert suggests something else. He then moves onto counting fire trucks, and finally balloons. Ernie imagines blowing up a balloon, which gets so big that it explodes loudly, causing Bert to scream.

Ernie: Um... one?

Follow That Bird

One of the Sleaze brothers barks at the two kids, as if he's got a guard dog.

Sam Sleaze: Hey kids! Get away from the talent! Go on! Scram! WOOF WOOF! WOOF WOOF WOOF WOOF WOOF! Haha!

Cookie Monster keeps eating the car he's riding on while they search for Big Bird.

Gordon: Cookie, will you stop eating the hubcap?
Cookie Monster: Road trips make me so hungry.
Olivia: But we haven't even started the trip yet.
Cookie Monster: That's okay. Me eat three other hubcaps later.
Gordon: Cookie!

Kermit's joke: "Why does the chicken not cross the road? Because it's chicken, get it?"
Cookie Monster's good-bye.

Cookie Monster: Don't forget to eat!
Big Bird: I won't, Cookie Monster.

Grover's good-bye is arguably even funnier.

Grover: Don't forget to breathe! In and out!
Big Bird [without a trace of sarcasm]: I always do, Grover!

The Sleaze brothers looking for Big Bird.

Sid: Hey look. A haystack.
[Sam looks at a walking haystack, which is actually Big Bird hiding from Miss Finch]
Sam: We're not looking for haystacks, you chowder head. Keep your eyes peeled. Big Bird's gotta be around here somewhere.

Super Grover falls into the yellow bug, thinking he's found Big Bird.

Super Grover: [his cape covers his eyes] Big Bird! Big Bird! I found you! Big Bird! Big-- [Olivia removes the cape] This is not Big Bird. You are imposters.
Gordon: Grover.
Olivia: Grover.
Super Grover: Super Grover please. When's lunch? Hahaha.

The Sleaze brothers spotted Big Bird.

Sam: Big yellow bird at 1 o'clock.
Sid: Is that late already?
Sam: Its air force talk, you nerf!

When the Sleaze brothers capture Big Bird:

Big Bird: Do you mind if I hide in your fun fair?
Sam: Why no. Not at all. We have the perfect place for you to hide. Right here: in our "hiding cage".
[The brothers lock him in]
Sam: You'll be safe here.
Sid: Yeah, real safe.
Big Bird: Gee, thanks.
[The brothers laugh]

- Later...

[The Sleaze brothers are playing cards]
Big Bird: Hey guys, you can let me out now. Is it safe now? Can I get out now?
Sam: What's the matter, don't you like our cage?
Big Bird: My cage? My-- my- my-- MY CAGE!?

The Sleaze brothers arrested:

Officer: You can tell that... to the judge.
Sid: [crying like a baby] The judge.
Officer: Be a man!
Sid: But I don't wanna be a man.
Sam: SHUT UP, SID! SHUT UP!

Sid: [still crying] Judge... jail...

Bert and Ernie lookout:

Bert: What do you see, Ernie?
Ernie: Your nose, Bert.

Gordon trying to get Big Bird to jump into the Beetle:

Big Bird: You should never jump from a moving truck! Why... I shouldn't even be standing up!

Gordon: You have my permission! Just this once. NOW, COME ON!

- Earlier:

Gordon: Come on!
Big Bird: Come on? Gordon, you know I can't fly.
[inside the car]
Sid: I got an idea! What if we built a big high tower, and he jumps down into a pool of water?
[outside]
Big Bird: Jump?!
[inside]
Sam: Nah! He's a chicken.

Everything about the Grouch Diner. Especially the tossed salad.
- Cream of mushroom soup, eaten by itself, is revolting: it's an ingredient, not a food. The Grouch Diner serves cream of mushroom soup with maraschino cherries.

Maria: There's nothing here I can eat!

Elmo in Grouchland

Just about every time Bert and Ernie appear on-screen is hilarious, but this scene in particular:

Bert: Elmo didn't get his blanket back! This is terrible! How can it end this way? It's so sad, oh, it's so sad...
Ernie (trying to interrupt): Oh, no, no, no, no... Bert, Bert, Bert -- no, Bert, Bert, listen --
Bert: Don't -- don't 'Bert' me! This is -- this is terrible...
Ernie (still trying to interrupt): No, it's okay, Bert, the movie's not over yet!
(Beat.)
Bert: Oh.
Ernie: Mm-hmm.
Bert: You mean good things could still happen?
Ernie: Of course they can, Bert! In fact, I'm sure good things will happen, because...who'd wanna see a movie with a sad ending, Bert?
(Beat.)
Bert: Titanic.
Ernie: What?
Bert: Titanic had a sad ending.
Ernie: Uh... no, Bert. Uh... Roll the film! C'mon, Bert. C'mon...
Bert (as Ernie ushers him off-screen) Gone with the Wind. Doctor Zhivago.

The jail scene gets two CMOFs right after one another:
- First when Big Bird starts singing the Alphabet song to cheer his Grouch cellmates up, and they panic, screaming: "Lemme outta here! It's torture! Let us out!"
- Then, immediately afterwards, we get this gem of a scene with Gordon and Telly:

Telly (rattling the bars of his cell door): That's it! That's it! I can't take it anymore! I demand justice! I want a lawyer! CALL THE MEDIA! START A DEFENSE FUND!
Gordon: Calm down -- calm down, Telly! Let me get you some water. (calling out to the guard) Hey! Can we get some water in here?
(Gordon promptly gets a bucket of water thrown at him.)
Gordon: ...Thanks.

Telly (looking at the soaking wet Gordon, holding out his cup): I didn't get any.

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