Top 20 Funniest Dean Winchester Moments on Supernatural

[@MsMojo]

Is there a Dean moment YOU find awesomely hilarious that we forgot? Let us know below, and check out our video of the Top 10 Things ONLY Supernatural Fans Understand - kzbin.info/www/bejne/eWq6c2WHhNWZns0

[@Swearengen1980]

Did you actually say out the full, correct alphabet communities numbers/letters/symbols?

[@lucindamorningstar9108]

When Dean's baby was abducted and he nearly has a heart attack. I've always wondered if the extra in the background was an actor or a "real" person 😂

[@vanmoody]

In Folsom Prison Blues Dean makes a comment about how he heard something in the yard. Sam looks at him and says, "Dean, does it bother you how well you fit in here?"

[@elizabethjones7309]

What about the turduken sandwich? His comment was hilarious.

[@chelseacanales8763]

Him arguing with a pigeon is still hilarious to watch along with him lip syncing to All Out of Love

[@Georgi343]

Love that series

[@mariamorgan9817]

Yelling "Hey! Hey!" at mailman as the dog barks is great too! 😂

[@michaelpetersen6579]

While babys on lock down. Nobody puts baby in a corner. You know that's a line from Swayze always gets a pass 😅😅😅😅. Lol I'm so glad somebody remembered him singing air supply 😅😅. They forgot him saying I killed hitler to everyone he knew 😅. I just rewatched most of the series and I'm on season 14 and mannn it used to be there was one or two episodes that were so so and now it's like there's maybe 1 or 2 episodes that are okay and rest are pretty bad. I love him as Soldier Boy in The Boys.

[@dracrorasco4907]

What's really funny about that Batman line is Jensen Ackles would go on to voice Batman

[@comora010304]

Don't forget Red Hood. It's kinda interesting that he has 2 batfamily members under his belt

[@RandyWhite-e6t]

And people want him to play Batman in James gunn’s dc universe

[@Khaleesi_Jack]

There’s 15 years of funny moments. This list barely scratches the surface.

[@athenalindsey]

Knowing he actually acted in a soap opera makes everything funnier and intriguing 😅

[@shivermetimbers6128]

He was only on Days of Our Lives for a couple of years but he was ridiculously popular

[@roginal1677]

I loved him on Days. He's the whole reason I started watching Supernatural in the first place.

[@rcschmidt668]

Don’t forget Smallville.

[@raynevonwerner8695]

​@@roginal1677same!

[@Lost_feline613]

@@roginal1677my reason too lol😂

[@caseymacmacl7463]

Supernatural is one of the shows my son and I watched together. To this day, simply exclaiming "PUDDING!" is a guaranteed way to make either of us laugh. 🤣🤣

[@MsMojo]

Love that!

[@haley4699]

Still the single funniest scene to this day for me lol

[@mariamorgan9817]

Same thing with my daughter. 😁

[@niyanlan8928]

I loved the one when he found out he was fighting gods scribe - Metatron. He explained in frustration - ‘what, we’re supposed to fight transformers now?’ Priceless.

[@dianastella]

That one had me screaming 😂😂😂

[@RandomFandomDragon]

I thought Sam was the one who said that, because Dean corrects him that the name is Megatron

[@funtimes8409]

@@RandomFandomDragonyou are correct

[@feralart]

His Scoobynatural moments.

[@joiedevivre2005]

Best crossover EVER!!!

[@koncan5]

Sam. SAM. LOOK OW BIG MY MOUTH IS!

[@ameliacrowther-davies6458]

Dean Winchester content?!?! In 2024!?! Dream come true baby!

[@RandyWhite-e6t]

I misread the last part as Dean come true

[@georgec7782]

I don't know what was funnier: the scream or him saying "that was scary!"

[@katerinasimpson1100]

There’s so many awesomely hilarious Dean moments that it’s impossible to choose just one. Sam and Dean (and Cas too) forever. The irony of the demon karaoke is that Jensen is actually a really good singer.

[@icynishia1723]

Honestly. Hes in a band called radio company i think. His music is good. Kinda country/soulful blues type of music

[@athenalindsey]

I could watch this man all day 🤣

[@MelaninMuva]

I know a lot of ppl 💩 on this show but I literally grew up with “Sam & Dean”. I was a senior in high school when it premiered and by the time it ended, I was married with 3 kids. I never missed an episode no matter how bad it got and boy, it was truly touch and go for a little while 😂 but I still love this show to this day so I’m super stoked that Dean got his own list 🤗

[@michaelpetersen6579]

You ain't lying. I was 25 when it started but I didn't know about it until it's 5 season because my ma told me about it. I was like okay I'll give it a go and man I binged watched it to catch up with her and we watched every episode from then on. In my opinion every season up until then had a few episodes that weren't good but in the last 2 and a half seasons in my opinion Unfortunately there was only a few episodes that were okay. Covid really screwed up the ending. I loved supernatural because it was a great time watching it and spending time with my ma. I love Jensen as Soldier Boy in The Boys and I think we might see him blow up even more because of that role. Did you watch it with your partner or was it just your thing?

[@jennagisclair3058]

No mention of anything from Changing Channels???? The whole scene where they play detectives alone is great. His comments in the beginning about Dr. Sexy. When he plays the sit-com role and does his Son of a B*tch line are all fantastic.

[@lazonfutura2872]

The episode with Linda Blair, when Dean mentioned he was hungry and thought pea soup sounded good makes me laugh every time. It's a line we often repeat at our house.

[@Shamboopy_]

I really don’t know how to explain it, but whenever I watch the show, I just felt at home and comfortable. It was just one of those things that you never wanted to end.

[@ItsJustCiCi]

Yes! 🙌🏾 This warms my little supernatural loving heart! ♥️ more SPN content please! 😊 I love when Bella had baby towed and Dean asked Sam if he could shoot her. Sam replied with not in public 🤭

[@matthewvorwald7169]

Dean easily has the best funniest moments on Supernatural. And some of these are so much fun when you find out that Jensen Ackles improvised some of these scenes himself. One of my favorites will always be the moment when he finds out that Bela took their winning lottery tickets, and when he says that infamous line, you can see Jared couldn't keep a straight face.

[@KuriyanJei]

what's the line?

[@Americangirl1991]

​@@KuriyanJeiHe yells "sonofa*****"

[@genageeraert8039]

Scaredy cat is my all time favourite moment

[@louielucifer]

How could you not include Dean's love of pie!!!

[@devilspice7042]

“Son of a bitch!” Priceless.🤣 I also love the fact that Jared wasn’t expecting Jensen to do that and he tried to hide his laugh.😂

[@firehawk2324]

I mean... it's canon that Dean's favorite movie genre is Rom-Com, so it's not hard to imagine he also loves Finding Nemo.

[@achimdemus-holzhaeuser1233]

Also it's a known fact that Men are allowed to cry at the Toy Story Movies

[@RandyWhite-e6t]

Finding not fining

[@firehawk2324]

@@RandyWhite-e6t thank you. My previous keyboard had a falling out with the letter D so it was replaced.

[@haley4699]

My favorite two lines: "PUDDING!" and "Their human?!". They never get old

[@cookiesncream789]

I love how Supernatural is meant to be a horror show but there is so much comedy in it 😂😂😂.

[@mortimerbrewster3671]

I don't think the show would have lasted 15 seasons if it didn't have the humor.

[@richieagame503]

The scream in ghost sickness was so funny. That episode as a whole is so good.

[@mrandisg]

"Eye of the Tiger" will ALWAYS be my favorite, hands down! Not just hilarious, but sexy AF!!!! 🥰🥰😍😍🤩🤩

[@kimarmstrong2010]

#2 is my very fav! That scream gets me every time lmao

[@Chapter_1997]

Thought for sure the scene where Dean's asked if he has anything that's real by a cop and he says, "My boobs," with a smile was going to be on here

[@A4Kelly]

same. iconic dean moment from the pilot. sets the tone for the entire show

[@tinagiordanella3212]

You forgot the scene where Dean admits he's a Swiftie lol.

[@tracydoyle2512]

I love his facial expressions in "Just My Imagination". Richard Speight Jr ( Archangel Gabriel) did an excellent job directing the episode! The part where he makes the joke about the whole family showering together then realizes he messed up is great. But the best part is when he makes the joke about the mermaid. He fixes his face then tries to act serious. It's so well acted by him.

[@shannonmorris-f2t]

My favourite Dean moment is when Sam and Dean were in the antique shop and he kept dropping the model ship 😂😂😂

[@AC005]

Should of had the eye of the tiger outtake even if it was an honorable mention where it not techically 'Dean'

[@Desaki65]

Hear hear! I love that outtake so much!

[@phoenixflare07]

literally came in the comments to see if anyone else was like "Where is freaking eye of the tiger?!" It still made the cut for the end of the episode so technically it was a part of an actual episode even if an outtake.

[@daisysunshine1324]

It might be an outtake, but it’s massively loved by all of us.

[@kiddisskat]

ikr?! That’s my fave scene of the entire series 😅❤

[@mrandisg]

Yep. "Pudding!" is cute, but nothing tops "Eye of the Tiger!" Except maybe "I'm Batman." That's a close second.

[@art.of.verser]

Has there ever been a time when Dean Winchester DIDN'T make us bust a gut (so to speak)? All I know is that the episode "Tall Tales" definitely cracked me up the hardest the more I watched it, especially those supposed scenarios with Dean being a total highlight. Oh, yeah, as well as that freaking Batman line of his when he ends up with a lot of good luck while saving Sam. But, seriously, HE'S FREAKING BATMAN!!! 😂

[@yondu689]

The one where he gets old playing cards with the witch was good.

[@SongbirdRebel]

PUDDING!!! that and the cat scream are one of my favorites

[@comora010304]

I love it when he freaks out trying to bother Sam, when both talk in sync on the loop day in the cafe 😂

[@sarahswitzer5846]

The episode is mystery spot

[@lacyInmon1978]

I will always be a Dean Winchester fan. I have been a Supernatural fan since day one.

[@tanz_divianfaizian]

I can watch anything on Jensen and Dean all day😊😊😊.

[@sagefoole]

My favorite Dean moment was when he had to talk to Demon Snooki! Hilarious!!!

[@TrinityRodas]

Everyone wants a man that has a sense of humor and doesn't take himself too seriously! Goals!

[@crystalshaw8744]

" You fight those fairies "😂😂😂

[@heatherlyncleare1706]

Love the second one with the cat. The dog at the beginning was really funny too❤

[@MrRonald327]

He’s the real star of the series!

[@gregkral4467]

I loved the outtake of when dean was scared of everything, and he was lip synching eye of the tiger in and on baby..... he rocked it.

[@VampColt]

When the guys were at the cemetery with Bela, destroying the rabbit’s foot. She takes his lottery tickets he won and when he realizes, he yells “Sonofa*****” while Bela honked and drive away with the lottery tickets. I laugh so hard on that and you also see Jared aka Sam trying to hide his smile to laughter.

[@sunflowers47]

In The French Mistake Dean ans Sam go to Jared's house and find out that he married "Ruby". Also I love the line "You fudging touch me again and I'll fudging kill you!" From season 3 episode 8 "A Very Supernatural Christmas"

[@mrandisg]

Yes! The "fudging" line! I love that!!!

[@MGG87]

"Scaredy cat" will always be my favorite Dean moment.

[@joiedevivre2005]

Surprised the episode where he gambled away years of his life & became an old man didn't make the list. The Dog Dean, the Multiple Dean Deaths & the Scaredy Cat episodes are definitely my favorites.

[@carolynsanders2972]

I love this incredible show ❤️. It has to be the best series. Hopefully, they will bring the show back. They are all my favorite. Scary Cat was so funny. 😂 I have watched TV for over 10 years. Until my sister moved in with me. I lost my son, Michael, to a drunk driver. She turned on the show for me, and after 10 years I was finally able to laugh again. God bless you all. 🙏

[@MissWocyBear]

🫂💞

[@alltheworldsastage4785]

The guy is a riot! 😂 What's equally funny to Jensen (Dean's) wit, is Jared's facial reactions when he encounters weird circumstances. 😂😂

[@crystalshaw8744]

I haven't seen him in alot of episodes of Supernatural, but I love him in The Boys.

[@TheFirst_No_L]

The Batman line is even more funnier seeing as he voiced Batman

[@MrRaziel25]

YEA especially when they go cartoon and dean goes crazy for daphne on scooby doo

[@mooseman1754]

My favorite character from my favorite show 😂. There are too many to fit but one of the episodes I always thought was funny was 5-7 “The curious case of Dean Winchester” he turns into an old man and Bobby just adds to the humor…would be funny to do a Bobby version of this too now that I think of it.

[@missenceladus]

My favorite Winchester ❤

[@TBuchan]

"I killed Hitler" for the fact Dean comes to this realization and then proceeds to bring it up repeatedly in following episodes and is just so proud of himself lol

[@Oktopia]

Pure gold. Dean would fight us to the death if we suggested it, but we all know he's the comical sidekick. :D

[@imanassole9421]

"Pudding!" I freaking died🤣🤣

[@victoriashore1332]

Why did you cut out “That was scary”? That’s the best part of that scene

[@alltheworldsastage4785]

One of the funniest moments from Dean, was when he butted heads with the Angel Uriel, Dean asked Uriel to leave so he could speak to Castiel alone, Uriel reluctantly agrees, and responds with: "I'll go seek revelation, Heaven may have further orders" as a way to put pressure on Dean before he leaves, but Dean's response was so funny, that even Uriel laughed his ass off, Dean, without missing a beat, immediately responds: "Well, get some donuts while you're out." 😂 That should have been on this list.

[@Traci2000]

There's just way, way too many funny moments to fit in one video, lol. I miss this show so much!

[@debbieduckworth9339]

The one where Dean is running from a dog. Sounds like a big scary ,but when we finally see it. It's just a very small dog but, he's hearing, I think it was hellhounds.

[@scheidttruevaluehardware6731]

The time Dean dressed up like Clint Eastwood. Was hilarious.

[@grimby44]

The whole scaredy cat episode is gold !

[@SingerBabyJay]

The moment at the end of the episode "yellow fever" when Dean #jensenackles sings #eyeofthetiger dancing along 😂 Its just the best!!

[@TiredOfApathy]

ScoobyNatural needed o be mentioned! And when Dean played Death for a day, that was classic. He's asked by a dead guy "What's this all mean?" Dean replies "Everything is dust in the wind." HAHAHAHAHA A freaking KANSAS SONG?! LMAO

[@MyVwccStar2023]

His moments in season 13, episode 16, along with this scene "I would have gotten away with it if it weren't for those meddling kids!" Dean: "He said it, he said the line....Scooby dooby doo!"😂😂

[@mikl12354]

Rowena will ALWAYS have a special place in my heart in this show. Yea she was a big bad but, when she showed emotion after learning about the death of crowley showed me that she may be evil, but shes still human. Shes more human than most in OUR world. I think thats why i like most of the villains who turned good in this show. It helps me cope and lets me think "If This EVIL person can be human, what stops our evil from being human too" Hell, Even LUCIFER was trying to make a change for the good of things. Its just, No one gave him the chance and told him he was too late to change.

[@brb__bathroom]

the end of the series took a jackhammer to my heart

[@ofeliasevilla3264]

They made me cried a lot the last episode 20,season15,when Dean dying moment,they are both good.

[@carlblankenship8619]

"what's in the box?!" From the 7 deadly sins episode

[@sarahswitzer5846]

Magnificent seven episode

[@elizae2528]

Yaaaaaaass!😊😊😊❤ daddy! I love him! 😅😅😅😂

[@shielakay]

I always liked the lines in the benders when he tells them "eat me- oh wait you just might" and "demons i get, but people are crazy"

[@Ookami88]

Seriously? You forgot one of the most hilarious episodes, the one where Sam, Dean and even Cas get stuck in a Scooby-doo episode. The way Dean has fun with suddenly being a cartoon character and being able to chow down food exactly like Shaggy and Scooby, not to mention his failed attempts at wooing Daphne. How come such hilarious episode got omitted?

[@kimberleyrigg7503]

DW is one of my all time favourite characters - a funny badass.

[@kamron_thurmond]

I found his reactions when Dean met Sam's imaginary friend to be particularly funny. Also the Christmas episode where the wood nymph escapes containment in the bunker to have some pretty funny moments.

[@george.a_m]

Sheriff Jody Mills was also Zack and Cody’s mother in the Tipton hotel In case you recognised her but couldn’t place it

[@alltheworldsastage4785]

1:58 I remember laughing until tears came out of my eyes the first 😊time I saw this scene. 😂😂😂

[@JeffinIC]

What?!! No mention of "Eye of the Tiger"?!!! 🤯

[@Kleineganz]

Technically that wasn't Dean, that was Jensen during an outtake. Definitely one of the best "bloopers" though.

[@DravenGal]

You did forget one! The "Eye of The Tiger" scene! Shoulda been number 1!

[@jaked.6386]

"NOBODY LIKES BEING IN THE CAR WITH YOU SAM...YOUR GASSY!!!....YOU EAT A BURRITO AND YOUR TOXIC!!!!"

[@msfeistybabe]

"We... are insane!!"

[@KuriyanJei]

didnt even include the "You got iced by a teenage mutant ninja angel?"

[@taylorsues302]

Eye of the tiger is my favorite outtake 🌟💥💖

[@pamelaJoyce384]

Pudding!!!!😅😅😅

[@AngelsHeart87]

15:00 When Jensen would look at me like he looked at the poodle... omg😍😵😅

[@cathytrottier8944]

Dying Dean Episode was an angel tying to get Sam to accept that he wouldn't always have Dean with him but yep really funny. Scaredy cat was hilarious I never knew he could hit that pitch.

[@ladykaia2000]

I loved it when he kept saying I kill Hitler

[@invadertifxiii]

Should definitely be a part 2 that includes the changing channels episode 😅

[@sikes442]

Nutcracker!!!!

[@jessicariley2114]

Last time you zapped me somewhere I didn’t poop for a week! (Talking to Cas) 😂

[@chadmoore4298]

The supernatural episode where Dean keeps diying is one of my absolute favorites.

[@DeannaBrownlee]

"IT'S NOT A TULPA."

[@Rando0962]

I've got a GED and a give em hell attitude is my fav

[@matthewcoger6274]

"My boobs" from the first episode isn't number 1 ? It set the tone of the whole series !

[@Soron661]

"I'm Batman" is not just funny cause of the seen, but because Jensen eventually gets to voice Batman in the Tomorrowverse. Now, I'm just waiting for him to get to portray The Dark Knight in a live-action series. Be it tv show, which would be better, or a movie franchise.

[@college87]

LOL I never saw the hairy hand episode lol

[@samuelcollantes1175]

Of course i agree. Happy tuesday afternoon, Emily. Take care and God bless you, greetings from Colombia to you as well.

[@Americangirl1991]

Supernatural will always be my favorite show. Dean is definitely my favorite character, aside from Cas. ❤️

[@Lcbdolpindm13]

You cant watch this show without seeing deans' manurisms they are hilarious

[@bratzmama]

Jensen is actually a very good singer so in any episode where Dean sings, Jensen is purposely singing badly. I've been a fan for years and always will be!

[@HomerSimpson-xo8vw]

Freaking Awesome 👍👍😎😎 Dean Winchester Rules ❤️❤️😎😎👍👍❤❤