15 favorite sad Dean Winchester scenes

[@TheRealDionysos]

I never understood why people almost never mentioned benny. He was damn loyal and probably next to cas deans best friend ever. He dyed for him... and his death was final until now.

[@shantasticc9095]

Ikr? I loved benny 😢

[@Shan04268]

I love Benny! One of my fave characters. They could have done so much more with him!

[@chrisf2471]

Benny Charlie and Kevin we're all so great

[@abdulshaik8802]

Died*

[@paige_nlmg]

Ikr that's so freaking sad that ue killed his bf

[@lauradufresne6628]

This is why I love Dean. He's a multi layered character. The tough, sarcastic outside hides how broken he is on the inside. And as usual Jensen continues to blow us away with the sad and angry scenes.

[@yenh1144]

And he can deliver funny scenes with ease too. I hope he has a good long career, it’s well deserved

[@toxicchemicals6736]

This is how I am in every day life

[@CAPTAINPRICE79]

God the way he says “He’s my brother” in the scene with Bobby breaks my heart. He sounds so utterly _broken_

[@yenh1144]

I watch that scene everytime I wanna tear up

[@cameronmichelson7457]

And then the broken voice when he tells Bobby to please don’t tell him, Jensen and Jared are the best actors they could have picked for their roles

[@Theo1442]

My cat was asleep and as soon as he heard Dean crying he woke up. I taught him well.

[@Cemoniepooh]

Yes you did 😗

[@dina5575]

yes yes u did

[@mageras973]

Good job

[@imgaynow5213]

Yes you did ❤️

[@terryramsey2377]

It just hurts to really realize how hard it is for dean😫😭

[@p4alls]

It's fine, I'm fine, I didn't need my heart anyway.

[@PrincessLorie]

Seriously!

[@randomperson2899]

Rips out own heart

[@derstummelacher2.042]

I feel you. If i could feel anymore

[@emrose6413]

Ain’t it one of the worse thing God gave “man”. 🤣😭

[@bobyvarghese9725]

Benny and Dean's relationship/bromance.. far too underrated. I loved that guys loyalty and he won't even blink to sacrifice himself for Dean. 💔💔

[@67Imp]

S i am sad when benny sacrifice himself for saving sam for Dean

[@christinejanis6552]

We needed Benny for longer, I'm so annoyed that they killed him off. I loved Benny so much

[@yenh1144]

Totally agree!

[@cerysheaps6258]

When dean argues with Mary that hurt me because we’ve seen what her death has done to them and how poorly she treated them in the beginning of being back.

[@amarkasamarkas9645]

Да уж,мать у них ,прямо скажем,не из лучших...

[@alondrabustos8066]

“Don’t you dare think that there is anything last or present that I would out in front of you” damn I haven’t thought of that line in forever. I dead ass almost cried when Dean said that.

[@alexroberts6432]

Past*

[@MyNameIsAshleyyy]

my favorite line..ever ❤❤❤❤ the nest ending then the angel's falling. Crowley looking up..Just perfection.

[@ml0723]

i think the scene where Sam first died and Dean talked to the corpse before selling his soul is pretty dang sad and is central to Dean as a character, explaining exactly why Dean goes to such lengths to save/protect his little brother. another scene would be where Jo and Ellen dies because I think that Jo's death has stuck around far more than people give it credit. there is a reason why Jo came back in the seventh season. i think Jo was Dean's one true shot at happiness that even Lisa couldn't deliver on because she couldn't understand or embrace what Dean is, what he's meant to be. Jo could have been that and it's one of the greatest tragedies of the show is that it was always the 'wrong place wrong time' with those two and they never got a chance.

[@roxiedoes7894]

Michael Lewis Totally agree!!

[@wanderlingd7047]

I always liked Dean with Joe I liked what she brought out in him I thought they were good for each other. Lisa was ok but she paled in comparison and Cassie just used him.

[@nhuelsenbeck6924]

And when Crowley talks about dean's self hatred

[@PandoraWolveCrow]

Me too

[@rosanevithal3492]

Concordo e eu torcia muito por eles 2

[@shhhlemmesleep]

Dean hitting his car is such a powerful scene though. First instance where the show made me all teary-eyed

[@lewishamilton.f1.44]

I thought dean was holding a sledgehammer in that scene instead of a crowbar

[@dr.little7311]

That scene with Jo and Dean is so underrated. Jo and Ellen’s death really broke my heart. Having her back and having that heart to heart with Dean was sorely needed.

[@milanivosevic4771]

Damn, I've never hated a character more than I hated Mary in that scene. The boys finally get her back, and she just runs off ( and it's to the people that tortured her kids ). I get that she needs time to ajust, the boys got that too, but come on. She says she's NOT JUST a mom, but, up until season 13, she never was for Sam ( and I think that's what hurts Dean the most ). Dean's " I never was" gets me every time. Edit: I aso like how, in that scene, Sam just lets Dean talk, without saying a word.

[@marymartindale884]

I agree 100%

[@קרןקליפה]

I love how sem lets dean talk because as a person whit sistera there's so many time where one sister isn't strong enough (mentally) to fight this fight so another sister fight instead of her and that's actually the look sem have in this part because it's like I don't want to have this fight but it's need to be done so thank you dean for doing it instead of me

[@PandoraWolveCrow]

Me too

[@bookwormgirl1852]

Finding out that Benny died in Purgatory made me cry when Dean found out in season fifteen

[@Saniiiiiiiii]

woahhhhhhh chilll, lmaoo season fifteen isnt outon netflix yet for meee

[@tb.dana4064]

Shush ur faceeeeee

[@fierce.savage7076]

SPOILER ALERT!!

[@Spud1210]

I wouldve put the episode where dean loses his memory and he is looking in the mirror and forgets his name as the no.1 spot

[@horatio899]

That was really sad

[@hirumayoichi21]

What ep is that?

[@isabellewilburn1046]

@@hirumayoichi21 S12 E11 Regarding Dean (makes me cry everytime)

[@DHARK1873]

The thing about the “then I shoulda never come back!” line is that Dean INSTANTLY thought about the mission- not one thought about the safety of being back in his reality... which is common for him. Sam sometimes does it, but seems to me like Dean is ALWAYS having that attitude. In a way, it’s also destructive because it’s part of his feeling of ‘this is all I’m good for- being a soldier’, but it’s also what helps them all get through and get the job done. It’s also what moves him to save Sam no matter what the cost is, you know, not just his love, but his sense of duty as well. That’s the thing, Dean doesn’t just save Sam for himself, but FOR Sam, FOR his parents and anyone else who needs Sam to stay alive. Dean’s not perfect of course, but so often he puts others before himself... and this has helped me treat my own siblings better. Thank you dear writers, for creating Dean Winchester! ♥️

[@cassiecampbell2017]

You know you are watching a great actor that you can analyze a scene and you can literally feel what their character is feeling, even when the character is hiding it on the outside. You want to cry when he cries because it feels real, it feels like it's coming from the gut. Sometimes I honestly forget that Dean isn't a real person. I forget that there is an actor playing him. Jensen is so underrated.

[@deadshotya0974]

I saw the fear in Sam when dean got mad in the scene of when cass and Sam tell him they used Gabriel’s grace to heal him.

[@Conssumed]

Dean vs Dean is one of my favourite scenes in Supernatural.

[@SweeteaDove]

Man vs Self in such a literal sense

[@hamzaazhar8673]

3:19 I love Sam's reaction. Man is one of the best freakin hunters, but this shows he is still the little brother to Dean.

[@theredalpha7290]

Pardon me, but what do you mean?

[@toushirozge]

@@theredalpha7290 I think he means that Sam regularly fights monsters with barely batting an eyelash, but the moment his big brother gets angry and violent he flinches and is scared.

[@jptheflipper3825]

Why does Supernatural have to be so heart-breaking, I sat and binge watched it from the start, spent the entire time either heartbroken, singing along to everything or just in awe of it.

[@maissa1983]

Dean and Jo deserved better!!! she was his one shot at happiness I feel like, they should bring her back... I mean they always bring people back!

[@adanyadupont2568]

What about Lisa and Ben?

[@Kwmn7]

Looks like resurrection happens for only a selected few.

[@issa4767]

I think Lisa was his saving grace. The show was originally ment to end with her Dean and Ben together after season 5

[@raniamaco7120]

Michael Jazz Lisa she's normal person I prefer jo bcz she is a good Hunter

[@andyaitken4243]

When Dean said goodbye at the door of the hospital with Lisa and her son that was a huge sacrifice as he loved her so much. The acting is impeccable and really drives home how damn good this show really is.

[@pkphantom]

Quite frankly, I would've found it immensely amusing if Benny was still around. Like, they had an angel, a demon and a werewolf as an ally for quite a while, if Benny wasn't dead the circle of badassery would've been complete

[@frankrappa4765]

Benny was a vampire

[@theredalpha7290]

And a son of Lucifer

[@pkphantom]

@@frankrappa4765 You missed the point, I'm saying it would've been epic to see them all around at the same time instead of being already dead

[@frankrappa4765]

@@pkphantom ok

[@SweeteaDove]

@@frankrappa4765 Garth

[@rosaliebarvik1960]

Dean talking about Hell gets me every time😭

[@roxiedoes7894]

No one does the famous OLT like Dean Winchester… (One lone tear)

[@kaelaminadeo226]

It’s a single man tear... there’s even a song

[@gemini72aust43]

Didn't the SPN crew call it the OPT... One Perfect Tear?😁

[@saanvil124]

Gemini72 Aust Yess...Jensen spoke about not in a panel

[@kpoplove6001]

He plays the emotions so well

[@cassiecampbell2017]

he plays everything so well

[@ruadhrose]

As sad and crushing as the scenes are I can’t help but wonder how can someone be so damned sexy while he’s crying. Jeezus.....😭🥵

[@sarahkopp661]

I usually never cry which is weird but these scenes... *Supernatural in general* gets me to cry all the time When Lisa got her memory erased...I cried When Sam died....I cried When Bobby died....I cried When Jo and Elena died...I cried When Castiel lost his grace/died...I cried When Dean and Sam went to hell...I cried It is just so God damn emotional...(my mother doesn't understand why I love this show but I don't care I have been watching Supernatural since I was 6 years old bench watching every episode of each season untill a new season came out. It's just sad to think season 15 might be the *LAST* episode 😭❤️😍

[@ABC-co8id]

Sarah Kopp yeah i can totally relate..i am sad too that the show is ending and I feel i cant find a replacement for supernatural ever..there’s no other show like this and no lead actor as gorgeous as Jensen!

[@alexroberts6432]

I hated Mary so so much, she was always acting so high and mighty and like the whole thing revolves around her and was such a horrible mother to the boys, acting like she was so innocent and trying to blame it on everything else

[@darkfang25]

The saddest thing is when Dean’s talking about Hell, and how he got off the rack. Sam tells him, “You lasted 30 years, that’s longer than anyone.” Then we learn that their Dad was supposed to be the one to break the first seal, but he outlasted it. That reassurance is just empty.

[@eleonoramaciel6273]

The way Benny laughs as if to make Dean feel better about killing him, but it's nervous nevertheless. One of the best friends Dean ever has and never betrayed him. Even in the end, he put Dean first, even when he knew he himself was beyond saving, he stilled pulled through. For Dean.

[@estherw8554]

I so wished he'd appear in an episode this season...

[@lauratroy13]

Wow their casting is so good that for a moment I thought the thumbnail was brock kelly as teen dean

[@jaime2662]

I will literally die crying to these scenes, thank you for posting this,

[@MommaO09]

I cried a thousand tears watching this. My heart breaks every time I see those bright green eyes well up.

[@HistorysArena]

This is the reason i love DEAN. And usual Jensen Ackels did the a great job. I mean how do you do it every time. You are just phenomenal.

[@taasfiafatemaprapti6243]

You should've kept the "I am proud of us" scene.That is one of my favourite scenes.

[@shelbydn6187]

That’s what I was thinking! That has always been my absolute favorite scene.

[@cass80xj]

regarding dean ep were dean tries to remember who he is & can't(the mirror scene) should be no1, not sacrifice, cs dean was once again emotionally manipulated on that 1. that scene was abt his brother's jealousy towards dean's relationship with cas & benny, than dean himself. while regarding dean was abt dean losing his memory, which was heartbreaking to watch & jensen nailed it as usual

[@amberxv4777]

Losing his memory isn't nearly as sad as sacrifice. Dean basically giving up on his whole quest to seal demons and letting the world be screwed because Sam will always come first. And with Dean actually confessing it and coming to terms with it. For me it was the saddest scene. It was right in the feels.

[@BabyScatha]

wow calling someone being suicidal for manipulation is low. Sam was so far down a whole lot in that scene because of Dean. "Saint" Dean can do no wrong pfft.

[@x4n7h05]

15:13 Seeing bobby again makes me cry Jesus Christ.

[@luigiluigi4366]

i thought to myself oh i got this easy but then dean talked about hell and oh god

[@kaelaminadeo226]

Cleveland brown the thing that blows my mind is that is the one scene that Jensen said he had to walk away before doing another shot because it got so emotional for him.

[@wanderlingd7047]

In response to the #1 scene when sam starts talking about Dean turning to angels and vampires and asking about "do you know what it feels like to watch your brother . . " Well Sam at least he didn't turn to a Demon instead of you . . .. Yep I went there.

[@sangitadasgupta5082]

Loved the video to the core!!!! Jensen is an amazing and an awesome actor. Each and every scene old or new he just broke my heart. S2, S3, S13...so many emotions but the acting never fails. He has given life to a character and that is his best gift to all of us....just love him so much!!

[@labra6860]

What an actor Jensen Ackles !!👍 I love!!💗 I'm a huge fan...But especially Dean Winchester😍😍😍 I like the story of friendship with Beni😊

[@mookiepook7808]

Say what you like about this show, it's comedy, it's weird, deep, bizarre, incredibly creative, innovative and exciting, it's philosophy is astounding, it's also some of the finest acting I've seen from such a committed cast, I'm so sad it's ending 😭😭😭 💔💔💔

[@rosespaulding2874]

Wow. Made me cry. Now I'm sad, especially with the show ending. Please show, don't end.

[@ThisIsTricky]

Was the scene between Dean and Lisa sad though? Lisa told him to go, sure, but she also told him to come back. She gave him the opportunity to do what he's always done, to go and continue doing a job that's shaped him for three decades of his life, while still offering him a place. Somewhere physical he could call home. And I think that's absolutely beautiful. For the first time since the fire, he had a place he might've called home. A place separate from his "work," where he could live and breathe peacefully, even if only for a little while. I think that this scene is absolutely beautiful, even if it is now impossible and out of reach.

[@kir0606]

"You should be able to see that I am ninety percent...crap" Yeah, this is how I feel. I can relate to Dean so much and I believe a lot of people feel the same. Jensen is such an amazing actor ❤

[@jonatane5374]

the saddest moment for me is when dean slowly loses his memory in front of the mirror

[@aviesmith8883]

Thanks for making me cry for 20 minutes straight. Needed that.

[@TammiTuthill]

Very nicely put together... had me crying on more than one of them.

[@Sultan11-MF]

Awesome actor

[@hayley1868]

You know watching this video twice in a day cause I can't stop myself from crying😭😭😭😭😖😖😖

[@DarkosaDarkRave]

Benny was such a treasure.

[@steph0711]

The whole situation with his mom broke my heart, but I really cried when he spoke to Lisa and Ben the final time after their memories were erased... I think those two were the only people (aside from Sam and all) Dean truly deeply loved with all his heart and they were the only "ticket to a normal life" for him. That face he makes just rips out my heart

[@kenzie0934]

Benny was forgotten about too quickly and it suckered :/

[@MrKhho100]

I really hope the final season ends with a family dinner. When I mean family, I mean Dean and his family joined along with everyone who has come and gone as dinner guests.

[@lindascanlon2831]

What about when Sam got stabbed & Dean held him & cried & screamed out his name so freaking heartbreaking ! When he finally tells Sam about his time in Hell should be # 1 every time I see it I get all chocked up & really cry hard he kills me even when tears don't come his eyes bring me to my knees so expressive & heartfelt ! Jensen is a fantastic actor & if this show was accepted in mainstream T V hed have definirly won an Emmy by now ! YOU ROCK !

[@jackiedragonfly2461]

So true! It's sad really that actors from genre shows never get the awards, the bigtime fame they deseve. Supernatural was so much a brilliant show, but for me, who hates horror-movies, it was always such a shame it was angled as a horror show. Especially since it is one of the finest drama, adventure and even comedy that has graced TV this millenium. I hope Jensen gets Batman, and everyone outside of SPN and The Boys gets to know him. The guy should have an Oscar in his future.

[@kaitlynj.7389]

Each and every one of these scenes is so well put together and acted out. The amount of heart and emotion Jensen puts into every scene he does is incredible, along with everyone else who has made supernatural one (if not) of the best TV shows! 👍❤

[@Jo-or1gi]

im 10 seconds in and tears are already welling up nO

[@audiroxanne]

I can't bare it when my boys cry...but hen I feel so much better after watching the bloopers.

[@Pntngbrn]

I love your compilations. Other people shorten the scenes and use crap music dubbed over. Very nice, very well done. Work by a true fan of our favorite show.

[@jaya4093]

The way they made Mary look when she came back hurt so much cuz she wasn't really there for the boys and jus wanted to leave when they never even had her in their life

[@Artisan1979]

15:27 It's in that moment that I see Dean just become a scared little boy and Bobby the surrogate father by this gesture of touching his face. In many ways Bobby was more of a father to the boys than John was and this screams it.

[@Bbbb-bj3df]

im a dean fan.. i like sam but there was sumthing abt him that made me like him from ep2 of season 1.. the one who sticks on the plan. the one who never give up on his brother coz srsly from s1 to s5 all abt it was for sam to be ok,. all he wants was for sum1 to trust and depend on yet sam, cass and d family member he trusts betrayed him again and again..it was such a heart breaking thing for me.. yes he pull back sam wen he got a shot for a normal life but wth!

[@amberxv4777]

Those scenes are unique definitely. I would also put Swan song ending since that scene is basically hurtwrenching. But season 8 Finale definitely deserve the spot. It's my second favorite ending. And one can't watch it without crying.

[@supernatural_loverwinchest2958]

16:00 I just want to hug him and cry

[@Sultan11-MF]

The end few scenes . Jensen nailed them 100 percent

[@hobabi]

bro i never watched supernatural for too long, i only watched season one, but i know so much about dean... i love him so much, i just want him to be happy the way he deserves to be

[@cassiecampbell2017]

you should continue watching!! trust me- it only gets better. Season 1+2 they are still trying to find their foothold(just trying to not get canceled) but season 3+.... man, you will get hooked on it. HIGHLY RECOMMEND!! lol I started watching during quarantine abt a month ago, I am all caught up now and this was the best decision I have made to stick with the show.

[@Arda-bz9by]

Fantastic video, as well as heartbreaking. Great choices, thanks for sharing this. One addition I would make would be Dean talking to Sam's corpse in AHBL Part 2, but you already had a scene from that episode. (Also, Mary & Dean scenes still make me just as frustrated as I was when I first watched them.)

[@sandraestraume961]

He knows how to make those sad scenes

[@you_r_my-world2288]

Dean is my celebrity crush ❤️.

[@india7140]

i already had some tears in my eyes but at the end when Sam was sobbing my eyes turned into waterfalls.

[@Sqwabbles_]

Cried till the end then the ending song scared the hell out of me. So unexpected

[@cyriljude3033]

The line, "I never had one(Childhood)." Hit me harder than concrete wall. Can relate.

[@flaviadanielle3285]

Love Dean Winchester ⭐💖✨The Best actor 💖

[@roseolson1707]

7:27 I hate how Dean doesn’t have a response to anything Dean #2 is saying because he believes it’s true...

[@saijtarbox8159]

WHY AM I WATCHING THIS??!!😥😫😭😭😭😭😭

[@amberr907]

15:32 when I first watched this scene I tried so hard not to cry cuz i was in the same room as my mom

[@KM-vc9fb]

I’ve been watching edits for the past 3 hours. I came across this one and was like “wow great. I freaking love dean!” Half way in I saw like “why are these all so sad??” Then I read the title again. Congratulations I played myself and now I’m crying at 5am.

[@killikhivemind2776]

In Dean and Mary's argument. Everyone talks about the "I never was" line and it is truly gold. But I think the line where Dean refers to his mother by her first name. That was SO heavy. Show had its dull moments as it dragged on but they always knew how to make the big talks hit.

[@lindascanlon2831]

I think the no 1 spot is more the saddest scene for Sam not Dean but thanks for posting ! MY fave is when Sam gets stabbed & hes holding him & yells out Saaammm !

[@cameronmichelson7457]

That Lisa and Ben scene always kills me, he was so close to a real family but his past life ruined it😭

[@fiercewool5899]

I like this and all but it bothers me how the scene where dean was losing his memories and he started to cry while reciting his name. That’s my favorite sad Dean part because it really gets to you, but, overall great video loved it and reminded me of a bunch of old scenes

[@gabrielagarza9029]

#1 is one of my favorite scenes. I just love it and it makes feel so sad that Sam feels that way. Amazing acting by both Jensen and Jared.

[@earlaaaa]

Thanks didn't know a deadass like me could cry for 20 and a half minutes straight I mean how could I not subscribe-

[@ninjaeris131]

#13-I don't think I've ever really seen Sam flinch like that, like a scared kid.😢

[@SmallWorldFilms]

What you wrote to your viewers is lovely! Thank you.

[@rubyv5755]

I like every sad Dean and Castiel scene

[@alyssa2193]

I was very close to crying at around two and a half minutes but after that it was hard but I managed not to cry.

[@Jamiday13]

That is a beautiful message. Thank you.

[@blarmy827]

Benny 😭😭😭😭😭😭😭😭😭😭😭😭 I bawled like a baby during that and all of them lol

[@anitasingh4696]

God why did you give me feeling?!?

[@adriennemccue]

That first was the best... loved how Jared played that hurt of self-worth he feels.

[@denisehedden5108]

🖤🥀So sad moments with Dean. He's a powerful actor living proof that's what it truly takes to be able to show his talents through hell and back🥀🖤☝️

[@kirstenmcclain4489]

All the things he says to him mom, I wish I said that to my dad

[@zeeshanj2732]

At 5:10 when Dean was washed his hands each time a new face showed, I think it is because he is trying to was their blood off his hands(figuratively, of course). That's why it gets more and more vigorous each time. P.S : If anybody said this earlier, then I'm sorry. I thought about this right now and wanted to share it with everyone.

[@-_leslielopez_-1619]

The description is on a whole other level.

[@roku89107]

So many underrated scenes with Dean and Bobby

[@hayley1868]

Always crying out my hearts on seeing these videos. These videos are an important part of my daily life cause there is so much in dean that I can relate to in my big brother so in a way he is my big brother😭😭😭😭 can't stop crying after these videos THANKS A LOT you know I really feel that the producers should have created a little sister to go with those boys and that little sister would stick with dean in all his difficult times and keep him sane at least he deserves that much. What do you think?? Let me know.......

[@TammiTuthill]

Well... he had one in Charlie... said it himself. But I agree... Dean is everyone's big brother.

[@hayley1868]

Tammi Tuthill I mean yes he had charlie as a sister but I was saying like a real sister his own blood who would be there for them in hard times.🙆🙆🙆 maybe the producers should rewrite the whole series joining a little sister with them. Thanks for the reply by the way

[@Arda-bz9by]

@@hayley1868 "Family don't end in blood, but it doesn't start there either."

[@steeltoe9146]

No doubt i live my emotions through Dean tough as nails on the exterior BUT a ocean of emotions underneath

[@tonycoleman2184]

I do wish they'd make a video that focuses on good aspects of his character

[@David13579]

15:07 Okay that just breaks my heart 11:54 that’s a pretty intense scene 18:26 Guys, woah, please staaaaaaaahhhp 😢