Jonathan Winters FUNNIEST Moments Ever! HT

 

A lot of people say, you know, how are we doing? What does this mean? Why can’t you say, how are you doing? You know, but they say that in hospitals, how are we today? Not good.    Jonathan Winters’ perfect impersonations and delivery made him one of the funniest comedians of all time. Uh my father uh said, what are you going to do, kid? You haven’t done anything for the last 3 years with yourself.

 Of course, when I was a corporal, I mean, that was a big thing to me. I was told that if you made corporal, you was good as a general. Yeah, and I believe that.    These are Jonathan Winters’ funniest moments ever. Winters with Dean Martin. He’s rude, Margaret. Can I light your on the television? Sweet, boost.

Well, I sweat what time we take a lobster night. Wait, they wait a little good shuffle. Short. Hey, little devil.    And love him here, touch him on the leg a little bit. Have a little kiss, huh? How you doing? Well, I forgot it, forgot    I didn’t get into this thing, boy. I was flying out to can incidentally let me give you my name.

 I’m I’m Howard Stuffelfinger. The American Kindling Company. Anytime you want any kindling, lay it on me, sweetheart.    I’ll give you all the sticks you need. Dean stays cool while Jonathan keeps making everything stranger looking like he’s inventing half the bit right in front of you.

 Winters’ 1988 Tonight Show appearance. These little surprises. Everybody out OF THE POOL.  [applause]  LET THE YOUNG PEOPLE STAY. DID YOU TAKE SWIMMING as a youngster? I I had no alternative. Uh the tough guys on the farm used to drag me through the creek. Why, I was very it was really bad taste and I you know, for mile after mile and you boy So, on the third day, of course, I I I learned learned to swim.

   A lot of frogs, you know, and kelp and stuff, but not kelp because they’re in creeks, but kelp is seaweed. I’m I’m rather quick on that. Winters turns normal answers into something weird so fast, never letting the conversation stay simple for long. Jonathan didn’t fit in the Marines. And I kept asking questions, which is always trouble.

Running up to a captain, you know, or colonel like yourself and saying, where are we, sir? On your business. Move out.    I was ALWAYS MOVING OUT. I WAS frightened a great deal of time. Uh I was frightened of the guys. I I didn’t understand a lot of them. They didn’t understand me.

 I was kidding all the time, you know, I being grandma one minute    Hi, honey. That’s good. A lot of guys didn’t understand. That would shake up a barracks late at night. down and I’ll never forget to a full bird, full bird, bird colonel, and did a voice on him which I’ll never forget and I said, oh, sir, what is your name? The story keeps growing while he tells it like it’s just normal life, making himself sound tough and completely out of place. The stick on Jack Paar.

Uh send in the smaller ones. I should like to play for you now an old tune that I played when I was in Vienna. It’s called “Und steigen auf zu Kölner nach Dürnstein an der Donau.” Which means along the river we go. Imagine what I could do if I had the other part. Doctor, I’m not kidding. I seen them Beatles and this is one of their failures.

Jonathan takes a tiny premise and turns it into a huge performance, acting like the stick is the most important thing in the world. The American Comedy Awards moment. Fantastic, buddy. That outfit got me out of World War II. Poor outfit.    We’re up in this area right now. We’ll get him home. I uh I don’t care whether you’re wondering or not why I didn’t wear a tuxedo.

I’ll tell you why. It doesn’t fit me. Uh He still feels sharp and playful, never sounding stiff or formal, even in a big award setting, bringing light, funny energy as soon as he starts talking. The Elwood Suggin Show with Dean Martin. Mr. Martin, are you are you out THERE ANYWHERE? YES.  [applause]  LISTEN, JUST JUST UH TAKE a seat right there. Let’s see.

 Is No, no, no, over here. Over here. Oh, I said take it.    Oh, you’re just like you are on TV. Yeah, you sit down there. Okay. Boy, that’s a that’s a good-looking suit. Oh, incidentally, this is uh made out by the Boyton brothers. Uh Howard Boyton puts these suits out for for me, makes them down there.

 People make them at the home. This moment’s hilarious because Jonathan completely disappears into the character, making Elwood feel like a real strange person rather than just telling jokes. Interview on the Jack Paar Show. Thank you, Jack. I I think you said I’m probably dying tonight. That’s    But I’ve had a full life.

38. Easy come, easy go. I had kind of a different day today. Uh Several things happened I can’t tell you about because uh they’d only embarrass you and embarrass me and have my family going. But I uh I did a thing that uh a lot of us uh probably would like to do. Maybe few of us don’t, I don’t know.

 I’ll just have to ask you. Did you ever undress in front of a dog? Winters feels exciting because it seems like he could say anything at any moment as Jack gives him space and Jonathan fills every second with strange turns. Teaching kids how to finger paint. Yeah, I made You really look like you’re something older than 8930.

 Well, I look old for my age. And my mother was old when she had me, she was 90. So, I inherited my genes. I Old man. Thank you. I’m going to show you how I paint. Now, look, see? We push that up there, over here a little bit, see? Now, pay attention. Just like school. And I take my finger.

 This is my finger, just like you guys. See, you’re doing all this, which is good. And that would probably bring as much as $100,000. This bit is funny because Jonathan acts like a serious teacher while everything keeps getting weirder, giving the whole thing strange authority that makes the nonsense even funnier.

 The gap between the serious tone and the ridiculous idea creates the entire comedic foundation. Has this happened to you? I had kind of a different day today. Uh Several things happened I can’t tell you about because uh they’d only embarrass you and embarrass me and have my family going. But I uh I did a thing that uh a lot of us uh probably would like to do.

 Maybe few of us don’t, I don’t know. I’ll just have to ask you. Did you ever undress in front of a dog? You think about that for a minute. I don’t know about people, you know, it’s funny. A a bird a bird somehow doesn’t count, right?    Or a cat. But a dog, they really stare.    This bit starts with an everyday idea, then slowly turns into something much crazier as Jonathan talks like he’s honestly explaining life to you.

 Winters and Art Carney. With a chicken. And of course, an elephant throwing a young man AGAINST A MOUNTAIN. THIS IS A BUG. OR A LIZARD. EATING A BUG. And you have a a MONGOOSE WHO’S TIRED. THIS CLIP IS GREAT because both [music] men seem happy to let the scene drift into chaos as Jonathan keeps pushing the moment into stranger places while Art Carney tries to stay with him.

 That back and forth gives the whole clip tremendous life, demonstrating two comedy veterans playing together without ego. Jonathan introduces unexpected elements mid-scene, forcing Carney to adapt his performance in real time. The scene starts with a simple premise that both actors immediately abandon for something more interesting.

 Carney’s attempts to maintain narrative structure get repeatedly derailed by Jonathan’s tangents, creating visible struggle. Neither actor tries dominating, instead building comedy through genuine collaborative exploration. Jonathan throws in non sequiturs that Carney somehow incorporates into his responses, showing professional skill.

 The moments when Carney nearly breaks character become their own source of humor. Their different comedy styles complement rather than compete with Carney grounding what Jonathan makes fly. Isaac Boothcourt with Dean Martin. Hello there. My name is uh Walter Stone and I’m with the National Broadcasting Company. We’re doing a survey on senior citizens.

 You don’t mind answering a few questions, do you? Well, I just wanted to Yeah. Uh people think I feed squirrels. I’m feeding kitty. Feeding the kitty nuts. Yes. Why what did you ask me? This isn’t a book about sex, is it?    No, no, no. I’m not a talker, I’M A DOER. JONATHAN builds this character so well that he feels like a real person as he doesn’t rush the joke, but lets odd details do the heavy lifting.

 Every line makes the character bigger and stranger while Dean staying straight-faced helps everything land even harder. Isaac Boothcourt gets introduced with a lengthy title suggesting an important government or academic position. Jonathan creates a pompous voice suggesting education mixed with inherent foolishness.

 The character discusses his supposed expertise in fields that either don’t exist or make no sense. He references past achievements that sound impressive until you realize they’re completely meaningless. Dean occasionally asks innocent questions that expose how little Isaac actually knows about anything. Jonathan gives Isaac verbal ticks like clearing his throat before saying something particularly stupid.

 The character name-drops famous people suggesting [music] connections that are obviously fabricated. Winters with Burt Reynolds. I’m sorry this is all we’ve got is just a telephone book. Yeah, and you make new friends that way. Okay. That was our regular shut-in call. We’ll make another one incidentally uh Mr. Mr.

 Bonlinger Hard Bonlinger puts these forks out. These are real good for hay around the barn or any place like that or uh or just like this. This is funny because Jonathan has more room to play throwing out voices, ideas, and little comic turns constantly while clearly enjoying the creative freedom. The whole thing feels like his imagination running free as Burt Reynolds mostly becomes a witness to the madness making Jonathan seem even more unpredictable.

 The show format allows him to shift between characters without explanations or transitions. He abandons bits midstream when new ideas arrive showing zero attachment to planned material. Reynolds appears genuinely charmed by the chaos occasionally trying to contribute, but mostly staying out of the way.

 Jonathan treats the show like a comedy laboratory testing how far he can push each moment. He cycles through regional accents, ethnic stereotypes, and age variations within single monologues. The lack of rigid structure creates genuine spontaneity that scripted shows can never replicate. Reynolds’ presence provides just enough grounding preventing the show from becoming completely incoherent.

Improvising with Robin Williams. Reverend Ainslie my hands are arthritic as you can tell. Well, just consider them not as hands anymore, but as paws. Be ready to do this. Get a little cat tree. Don’t be afraid. Say yes. Yes. Don’t be afraid. I’m going to put my hands on your head now.  No, but they’re in my hands.

 Why would you put your hand on my head? There’s nothing wrong with my head. IT’S A TWO-SHOT. GO WITH ME. IT’S A TWO-SHOT. Work with me now. Work with me, demon spirit. Bobby, get the extra. Look at MY HANDS. THEY’RE STRAIGHT OUT. THEY’RE STRAIGHT OUT. NOW NOW YOU CAN SERVE THINGS. Now you can serve things. Go table for tea. Table for tea.

No, but I can’t get them back that way. How do you get them back, Reverend Fred? Look, horrible, this is called mime syndrome. A tendency to be in a box for no reason for horrible long periods. Tendency to walk against the wind when there is no wind. Won’t you please help? A mime is a terrible thing to waste.

Jonathan never tries to match Robin by going faster, but stays calm and still gets huge laughs. Stand up on Smothers Brothers Show. What did you do with the comb? Well, he combed his sideburns. Yeah. Okay, I want you to have it. Do you have any pets? No, I don’t. Huh? That’s  Thank you very much.  In case you get one.

 Huh? Don’t blow on it cuz that’s No, eat it on. Cats have that in these mouths. Getting fever. This is a strong stand-up moment because Jonathan doesn’t need much setup as one voice or one strange thought carries the whole routine moving fast because he never stays in one place long. That freedom makes it feel like anything can happen next showing pure unfiltered stand-up energy.

 He abandons traditional joke structures in favor of pure character work and improvisation. The audience never knows whether bits were planned or spontaneous which adds excitement. He shifts perspectives mid-story becoming different characters having conversations with each other. The Smothers Brothers format gave comedians extended uninterrupted time creating space for experimentation.

Jonathan uses every second building momentum rather than letting energy flag. His willingness to follow tangents makes the act feel dangerously unpredictable rather than safely rehearsed. Some bits land harder than others, but he moves too fast for any individual moment to fail. He treats the stage as a discovery space rather than a delivery platform exploring ideas in real time.

 The crowd’s laughter sounds genuinely surprised suggesting they can’t predict what’s coming. Winters with Orson Welles. Who are you? Uh my name is John. I I know  John who? Davidson. I’m a singer. That’s Of course you are. John Davidson, well I’ve seen you before. Oh, a lovable guy. Yeah, I’ve seen you. Yeah, boy, real good.

 I really have to get some pictures taken. I’m going on a concert tour. You know what my problem is? I’m going on a concert tour and I have to be able to hand out pictures. People come back after the show and they say, “John, do you have any pictures?”  Yeah, of course I do. I want a picture that that would be sort of a sexy sort of a sexy picture.

 They come back to me  Please, I don’t want that. This is a strong final pick because the whole format gives Jonathan space to be himself as the show feels built specifically for his strange imagination. He jumps from one odd idea to the next without slowing down as that freedom makes the humor feel fresh and alive showing how great he was when given room.

 Orson Welles introducing the show adds unexpected gravitas to pure chaos creating deliberate contrast. Welles’ serious authoritative introduction gets immediately undercut by Jonathan’s madness. The variety format means no single idea needs sustaining beyond its natural lifespan preventing drag. Jonathan moves between sketches, characters, and bits with complete fluidity never repeating approaches.

 The production values support rather than constrain his creativity giving him props and sets when useful. He revisits successful characters like Maud Frickert while introducing entirely new ones within the same episode. The show proves he was more than a talented guest, but a complete creative force capable of carrying entire programs.

 Welles’ participation suggests the show had cultural ambitions beyond simple comedy programming. The 1972 production captures him at peak powers when his improvisational skills remained sharpest. Various segments showcase different aspects of his talent from physical comedy to vocal work to pure improvisation.

 The show format itself influenced later variety comedy demonstrating what television could do with proper creative freedom. Jonathan Winters was so drop-dead hilarious he became the blueprint for the funniest comedy and how total creativity and absolute commitment to whatever character or idea creates the funniest moments and crowd reactions.

 Which Jonathan Winters moment do you think was the funniest? Let us know in the comments and don’t forget to subscribe for more funny comedy moments.