Jailbreak ~ Tennessee Whiskey and Wagon Wheel

Jason, Rob & Friends at Jailbreak in Rome.
With Jason Manns, Rob Benedict, Jensen Ackles, Richard Speight Jr. and Timothy Omundson.
Best Jailbreak ever :D Thanks Guys for the awesome evening

[@annabellelee1073]

jensen's voice is as smooth as tennessee whiskey.

[@shannoncraig4790]

Annabelle Lee right! And both would go down so smooth!

[@wywardmoose]

aND jASON'S LIKE GOD DAMN

[@karleeward8711]

He’s sweet like strawberry wine

[@maryschaeffer944]

I would love to see how smooth he really is

[@meganennis9974]

Isn't it tho. And so rustic and soulful.

[@martinslvsten428]

Jenson sings so well that God is his backup singer

[@monlovchel]

🤣🤣🤣

[@nbdy__hr]

LMAO

[@e.d.m3076]

*Jensen

[@stellarzekia674]

this is brilliant- i cant- i love this

[@evasettgast8467]

Why is this so true 😫

[@briar7157]

Jensen: "no one can sing Tennessee Whiskey perfectly." Jensen: hits that run LIKE THAT

[@ShakespeareanWannabe]

Find someone who looks at you the way Rob Benedict looks at Jensen Ackles when he sings. Awe and wonder and amazement all in one

[@rysart2301]

I love rob so much he is such a great singer and I love Jensen too

[@denucci66]

Not awe, not amazement, nothing but pride.

[@emcer3543]

Did anyone else notice Rob's face at 2:35 when Jensen did that riff? That is everything to me.

[@peacefulsocialjustice9270]

Emily Hill Perfect

[@Xbitxx]

run not riff

[@emilysmith7142]

he looked like a proud dad

[@kristyperry8044]

Emily Cerros It's 2:39 😘

[@chadsanchez508]

That's really why chuck wanted to torment them.

[@Ca5ty]

I love how Rob/Chuck/God looks at the guys with this fatherly smile as if he's having 'yep, I made them. amen' moment^^

[@brittanyconrady3712]

Ca5ty I thought that exact thing!

[@SlapshotGritty2814]

Ca5ty Agreed.

[@katamstutz]

I was thinking that Rob looked at Jensen with adoration and that Jensen was impressed with Jason's vocals.

[@amandagantz1789]

Anyone else think Jensen could rock Chris Stapleton's "Broken Halos?"

[@AlaskaGuyette15]

Amanda Gantz omgg yess 😍😍

[@kaitlynnneal7041]

Yess

[@angieharris4402]

YES, yes and yes! Then imagine Misha, Richard and Alex sitting at his feet looking adoringly up at him as he sings it!! :)

[@otterlyemusing6688]

YES

[@katiewinter2314]

@@angieharris4402 Yes!😍😍😍😍😍😍

[@addykelly1777]

One of my favourite things about this cast is that even 99% of the men are a little in love with Jensen and think he’s so darn pretty and amazing. They all talk about it. It’s so cute. Like he brings out everyone’s inner 12 year old girl.

[@Wakaflockabach]

It'd be gay not to be be gay for Jensen Ackles.

[@emmasagers9118]

jensen's scruff will forever be the most wonderful thing on this earth

[@makailamcevers7397]

Yes thank you

[@onepunchman3922]

What's your snapchat babe?

[@makailamcevers7397]

@@onepunchman3922 what

[@ShakespeareanWannabe]

Those runs...remember when Jensen claimed he wasn't a good singer?

[@dizmen.d6960]

Link?

[@jenbranker4775]

He is a very modest guy

[@sandycubberley9250]

I couldn't get the link to take for me to post. Search Jibcon 2010 The Weight Jensen. The video shows Jensen with Jason Manns on stage. About 1 minute in Jensen is starting how "this wasn't supposed to happeb" and "I don't do this". He was so nervous! Look at him now ❤❤

[@saanvil124]

Here’s the link to the video: kzbin.info/www/bejne/in-wiWp-pNuFepo

[@AgentXv2]

Jen Branker without a doubt an absolutely exemplary human being

[@pettingbears]

You can tell he's nervous at the beginning but loosens up as it goes on. The "Tennessee Whiskey" riff is really difficult so I'm impressed that he pulled it off so well!

[@victoriashore1332]

I think one time in an interview he was having on the Tonight Show or one of those shows, he was acting all nervous and they were all surprised. and he said he gets nervous when it’s live. Even though he’s a professional actor. I thought that was interesting.

[@barebled]

Soldier boy been doing it for a while

[@soulfulhappiness6223]

Jesen hit that vibrato in the beginning i was like "JESUS!" "BRACE FOR IMPACT!!!!!"

[@laundrydetergent713]

These guys... dammit could the SPN cast be any more perfect?

[@aaronmontgomery2055]

more plaid?

[@Justasheepwithashepard]

Laundry Detergent I KNOW RIGHT

[@aceenby5674]

@@aaronmontgomery2055 I mean you're not wrong...

[@Entertainer145]

💫 Right 💫

[@weemidge3314]

Richard, man can he sing. Could the guy be more loveable? I mean I know most of you are here for Jensen or Rob or Jason but damn. I love the man with a passion.

[@ceciliacabrini]

WeeMidge I agree, a had to come back to Richard's part almost as many times and Jensen's. That Nashville accent is soooo good!

[@weemidge3314]

Ohhhh I knoww. I fell in love with his voice when I was about 13, watching Band of Brothers on BluRay with my dad on Sundays!

[@missymo8608]

Who is Jason? I see him all the time, but I have no idea who he is.

[@ceciliacabrini]

Missy Mo he is the tall guy with a lovely voice. At first he was just a friend of Jensen's who happened to be a singer, but through the years and conventions he became friends with the cast as well, even goes on tour with Rob. Now even the fans expect him to be at every con.

[@missymo8608]

Cecilia Cabrini thank you so much! I've been really confused and I was trying to think real hard if he was on the show or not.

[@spidey8us]

3:19 rob looks right at the camera with a look that says, "thats not the line, but at least he sings it well."

[@vleath1119]

For the first minute and a half, Jensen was me in any social interaction, I have never related so much to that man as now!

[@shekinahgonzalez3904]

jensen's face when rich starts singing tho like "yeah, that's my boy"

[@angelarobertson2668]

Shekinah Mikael right

[@hazelbell3067]

Does anyone else use Jensen’s singing as comfort when you can’t seem to stop crying other wise

[@zoeyaddison2365]

YES

[@collequ]

Yes gives me hope maybe there’s a chance to meet my own Jensen

[@laurenwinchester3902]

Doing just that

[@paulrobl7474]

always

[@veronicakenner4722]

I find comfort in Supernatural, behind the scenes, and conventions. Jensen is my safe place even if he doesn't know it.

[@aureaflamma2449]

2:33 it took me a hot second to realize that vocalization was Jensen. Showed this to my choir teacher and she's now obsessed XD

[@rysart2301]

She should be. My family doesn’t even watch supernatural or know abt he cast but when I put this song on it makes me happy so it makes them happy and they sing it

[@winniesmith8991]

I need Jensen to stop being so freaking amazing because I love him too much already and it is becoming unhealthy

[@KrisWolf4]

Join the club lol!!

[@sonjahesse1089]

I'm with ya there!

[@melaniethielmann3108]

Right?! He is amazing!

[@nikkibrowngodley859]

😂😂😂😂😷😷😷😷🤒🤒 he's killing me im dead im so in love😘😘😘

[@brendanewman2815]

Same

[@seeneembb8983]

I don't even like songs like this but their VOICES. JENSEN CAN RUN LIKE A KING OH MY GOD HE'S LIKE SCOTT HOYING. JASON IS JUST... OH MY. AND ROB, DONT GET ME STARTED

[@seeneembb8983]

And "Four Cheese" oh my god 😂

[@robing231]

I CAN RELATE TO THIS ON SO MANY LEVELS BUT YOUR PROFILE PICTURE MAKES IT EVEN BETTER. I

[@FFLCJT01]

I absolutely loooove Rob!!!

[@lexiplayz3284]

Omg I love this!! I feel like no one knows Scott!!!! You are so right

[@melissagray461]

Yess riffs and runs for days

[@hannahadams2312]

Nobody should be able to be as perfect as Jensen Ackles. I'm not complaining though

[@hannahtaylor26]

THE WAY ROB LOOKS AT JENSEN

[@angelarobertson2668]

hannah taylor yes !!!

[@maruchaansimpson5618]

Like he finally created something perfect;)))♡♡

[@jillbertothegreat9962]

OMG RICHARD I WAS NOT EXPECTING THAT!!!

[@alexhowe3861]

homeboy has an amaaaazing voice for Southern music.

[@angelarobertson2668]

Jillberto The Great same !!!

[@kittycat1291]

when they all started singing together it gave me chills, they are amazing

[@LeavesAbove]

I wasn’t a super fan of supernatural but I do remember Sam and dean popping up pretty frequently when I flipped between the channels. I watched the whole series after seeing this video because this is the song that played just before I got the news that my best friend had died of cancer. As you can imagine I fucked up the whole series for myself because now not only do I cry every time I hear the song but when I rewatch an episode just because I’m bored I also cry So I guess thank you, Jensen ackles, for making me make myself cry

[@cynthiah4478]

Holy Gabriel.. Richard has such a sweet voice!!

[@Jordanthefoo]

Soldier got the voice of angel

[@miriamleyva8744]

My eyes are leaking. Didn't even notice until I felt the tear run down my face. These guys. I swear.

[@ashleymedina9099]

Ugh i can't imagine how great it must feel to sing with your friends like this. I'm jealous. And they sound great, of course.

[@kaedasonata4432]

Is that, Timothy Omundson?!?! The sun doth shine on me, and my mother wearest thy drapes!!! I love Timothy Omundson!!!

[@briane.9743]

Seeing all them sing together is not just a Supernatural show...it's Supernatural Life above and beyond the show. 🥰

[@smurfettetutorialchannel8248]

Damb Jensen sang the hell outta that song

[@elizabethadams1228]

I’m sorry - did you just spell ‘damn’ like ‘lamb’

[@smurfettetutorialchannel8248]

@@elizabethadams1228 I did I'm guessing thats not the correct spelling

[@elizabethadams1228]

@@smurfettetutorialchannel8248 haha no it was funny

[@AnnaMassey96]

My God. Jensen singing Tennessee Whiskey. This is something I didn't know I ever needed.

[@mariehales5846]

He has a beautiful voice. And he's beautiful

[@sonjahesse1089]

Oh you definitely need it!!

[@jensenackles2484]

Hello

[@MsBrookie99]

We all needed it!! G%ck!!! My only adult crush!!

[@natashanelson-joy2415]

Jensen is a dark horse! Gorgeous guy, beautiful voice, generally nice demeanour and amazing actor! What a beautiful man 😍

[@kiara6262]

how can someone be that good looking, kind (as far as we know from interviews), a great actor and an amazing singer ?

[@julie_anne]

the second jensen and rob singing in sync im like "THEY SOUND SO GOOD TOGETHER SO MAKE A DAMN COLLAB"

[@morganl.kennedy3619]

That was the first time I heard Rick Speight sing! Hes awesome!

[@justanothersherlockian7058]

1) THAT RUN 2) THE HARMONIES HOLY SHIT 3) GOD'S BAND

[@magiv4205]

Their version of Wagon Wheel is like a hundred times better than the original. And not only because I love them so much, but the vocals and the especially instrumentals are MUCH more beautiful here.

[@ecstasiaburdened]

Magi V completely agree. The deep voices mixed with the high voices makes this, for me. And Dick’s verse just slayed this. Would love to hear him sing the first verse because I LOVE “pickin’ me a bouquet o’ dogwood flowers” 🎶

[@donovanyork1510]

Um. It’s pretty good but definitely not better than the original. Old crow medics show just are in a lane of their own. But still very good

[@timmcelyea8467]

You got to be kidding!!

[@Wakaflockabach]

​@@donovanyork1510they probably think Darius Rucker is the original...

[@topcheftoriko123]

Chuck, dean, cain an gabriel... What a combination of awesomeness!!

[@cheyenneh4759]

the way rob looks at jensen when he sings makes my heart melt

[@kyleightracy574]

Cheyenne H same

[@brooklynhinds8317]

Cheyenne H yesssssss I thought I was the only one who saw that lol

[@jenellis2185]

Cheyenne H the second I saw rob biting his lip and shaking his head I was like "same rob, same" 😂

[@eniojunior2237]

He did that cuz Jensen mistake the lyrics, so sorry :|

[@spnfan4ever978]

Enio Junior because jensen didn't really seem to know it that well, or at least not the Lyrics. because in the beginning you can hear him and Jason having a small convo before it started. This is what I heard: Jensen: Tennessee Whiskey? | Jason: *nods* | Jensen: I don't know it | Jason: do you wanna still do it, and just read the lines?| Jensen: *nods* yes ||| he didn't do too bad considering. I'm not trying to start something so i'm sorry if it comes across that way.

[@kim4707]

It seems like everyone from Supernatural can sing

[@AmySmith-to8jt]

Jason Manns + Jensen Ackles + Rob Benedict = pure perfection ❤❤❤

[@rebeccawright9508]

I could listen to these 3 sing anything. I love the way they blend their voices.

[@Shadow-rv4gn]

Awesome Jensen. Your talent knows no bounds.

[@ambergotwalt3613]

The bond with all of these guys is incredible!! Love seeing the cast members and all of their talents!! Long live SPN!!! So much love for you all from 🇺🇲

[@allegreetate6678]

Sweet baby Jesus on a scooter!

[@-equinox5252]

Richard singing gives me life

[@christyleffew1833]

Jensen: *starts singing Wagon Wheel* Me: OH ROCK ME MAMMA LIKE THE WIND IN THE RAIN

[@candaceharding4611]

The talent that man has crazy good

[@MILONICD]

God Job Soldier Boy

[@rosetrombley6106]

I love Jensen's singing so much he got me loving country music, love all he sings, he is so multitalented. ❤🎉

[@iamher00]

I’m in love with Jensen even more now ❤️❤️❤️

[@NannyMcfanny]

I’ve been avoiding Jenson singing as I thought he couldn’t be that good (nobody is that talented thought I) but how wrong I was !!!! ❤️❤️

[@ashm2266]

I love this so much, Jensen & Timothy singing together. & Chuck & the Trickster can sing too damn! they are all so full of talent.

[@janetlarsen8072]

Best show ever!!!! Great cast! Miss you guys, even still in 2023!

[@fjordhorsegirl1993]

to think the show only ended 3 years ago... seems like AGES it's been over

[@paralegalerika_s6389]

Rich melts my heart 7:12

[@jensenackles2484]

Hello thank you for been my fan how are you doing

[@jenyssmason9794]

Oh Richard! Your voice is so f..... perfect! I wanna record a song with you! That would be a dream.

[@cheesewhiz7124]

Rob's face seeing and hearing Jensen sing is exactly how my soul feels.

[@waywardqueen8985]

I keep watching all of these but forgetting to like or comment. But seriously, is there anything the SPN cast can't do? So many musicians, writers, and directors, aside from ya'know, being amazing actors. I love everything they give their fans..The panels, the meet and greets, and going out of their way to do things like this. Perfection. I seriously want there to be an album made with covers from the cast (I know Jason Manns has a cover album but one with everyone would be amazing. A benefit cover album for one of the many campaigns, they could raise so much money and make us all so happy!)

[@lightday2980]

WoW ! Jensen ... Just Beautiful ! Unbelievable . Your voice is ......... Just WoW !

[@avalonazure5488]

It is impossible not to grin in your god damn soul when you listen to Wagon Wheel

[@gracerobbins8505]

My mom loved Wagon Wheel as I was growing up, and countless visits to the beach included blasting the song on full blast. Hearing them sing it is so comforting

[@KrystleHamilton131]

I could listen to Jensen sing all day, I love his voice so much

[@karenculver4550]

FRIENDS FOR LIFE MAN,WHAT AN AMAZING GROUP OF ACTORS AND FRIENDS,I'M JEALOUS

[@Leoned91]

its nice to see how rob is humble when he gets praised so much, he is an awesome singer himself for sure

[@asimplestrawberry]

its embarrassing how quickly this became one of my comfort videos

[@billyhall3256]

Jensen ackles is the best singer that i have heard in a few years

[@sydshu5550]

Imagine these guys and Chris Stapleton performing together...

[@amyithistnichole5301]

Just when I thought I couldn't love this man more ... 🎉❤❤❤

[@MonikaS1890]

They shouldn't be allowed to stop singing...

[@angelarobertson2668]

Monocerosik right

[@morgankayleigh1709]

they need to have dean do it on the damn show

[@kenzh32]

Morgan Kayleigh they did now, his buddy’s bar before he fought his buddy

[@reginagle]

My husband’s favorite song for me and him to dance to. ❤❤

[@lottajcinthio531]

They sing Tennessee whiskey so so so amazingly good! I get shills form top to toe!😍

[@lottajcinthio531]

Rob😂 (4:55) "told ya" 😂

[@amyrissolo2079]

everyone here is as smooth as TN whiskey🥰

[@gemmacartwright7646]

Absolutely loved this. I love watching them sing together and enjoying themselves. ❤

[@soulofanartist2563]

2:33 gET thIs cHiLD a MedLe! That voice is heavenly

[@karencarver8094]

He can sing act and that voice. His wife is one lucky lady. Love this guy!!

[@bluzmaniac]

Wow two songs that need never be played again all together in one place. Happy new year to me

[@Wilma-de8sb]

Sweet and he's just so special 💕 we need to acknowledge him❤❤❤❤❤❤❤❤❤

[@brendaolivas2611]

My new favorite video on the Internet, ever. Dear lord. 😍😭❤️

[@blindkimberly1360]

When I heard Chris sing Tennessee Whiskey the first time I thought no one could ever do it as well. I was wrong. Beautifully done and a beautiful song. I love these guys!

[@kaylapotter-jones8448]

I love listening to these guys, they have amazing natural voices to listen too.

[@Dejam]

I love how even people like Jensen can get embarrassed and insecure for a moment. Shows we are all just human and it's ok not to be perfect.

[@freetobeme6013]

Love the chemistry between these guys.

[@michaelheinen563]

this is the supernatural/psych mashup I needed today lol

[@Wakaflockabach]

I wonder if Woody can sing? Bring him on for backup and Gus can tap dance

[@CoastDreamz]

Wow - just when I think I've heard everything his voice can do discover yet more. So awesome. He has such a deep, gravely voice when he speaks some times that it's a surprise when he sings like this. Awesome!

[@AngelaBouts]

Listening to Jenson sing is like being touched by A Angel his voice is so beautiful love you Jenson ❤😇❤

[@chandrarippe8790]

Gotta love a relaxed show. Couldve been rehearsed but had hiccups, could be on the spot jam session. Just music, friends and some people to appreciate it :)

[@paulaferguson2550]

So gorgeous with so many tallents. I could listen to you sing and watch you day and night. I love all that you are.

[@jaynefearn9505]

I do agree Jensen has a voice that melts your soul but let's also give credit to Jason Manns his voice is like velvet and it goes without saying Rob is amazing 💙💙💙 you guys rock 🎸

[@tiffanyglaspie563]

Harmony not only on set but in sweet music. Hell yeah…..

[@lottajcinthio531]

Jensen at 2:35 and Jason's high note #perfect❤️😍😇

[@EagerOnlooker]

All these voices make me smile! I loved the showcasing of everyone. So much love for these people!

[@SlapshotGritty2814]

Oh my chuck!! The three of them together? Gorgeous!!

[@adriennevrooman3603]

Okay I love Jensen but Richard on wagon wheel was amazing!

[@bellaboo4584]

Me watching this: 😳😢 They're voices are so calming, soothing, comforting and beautiful

[@how2497]

I KNOW RIGHT!! Like their voices are just Aaaaaaaah

[@bellaboo4584]

@@how2497 yess

[@cassietessa5911]

No, no, no... a human form cannot that be THAT perfect. HOW IS IT POSSIBLE?!