Top 10 Most Awkward Moments on Late Night

From Leno to Letterman, these are the most awkward moments on late night. For this list, we’re looking at interviews and encounters on late night TV shows that were just downright uncomfortable to watch. Our countdown includes when Joaquin Phoenix wasn’t having it, when Jimmy Kimmel mocked Jay Leno to his face, when David Letterman shredded Paris Hilton, and more! WatchMojo ranks most awkward moments on Late Night. What do you think was the most awkward late night moment? Let us know in the comments!
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#LateNight #JoaquinPhoenix #JimmyKimmel

[@WatchMojo]

For more great late night TV content, click here!: kzbin.info/www/bejne/Y3SkmI2VhdV6eaM

[@mlggamer5296]

Number 1: Everytime Trump shows up on Fox and Friends. Now I don't watch Fox much or at all but I've seen so many clips of him on Fox and Friends via comedians like Trevor and it's super hard to watch. They couldn't even get a word in! 😧😧😧 Also totally didn't know he was on Stephen Colbert as well

[@elijahmoreno4203]

Charles Manson is not a serial killer. He never killed anyone. he just got a few of he's followers to do it

[@stefanrichard4986]

Where's Farrah?

[@CoolPandaTheMovieNerd]

Something that you forgot, Cardi b on Jimmy Fallon, Rose McGowan on Stephen Colbert.

[@donking751]

The narrator needs to shut up!!!

[@VidaAnimada]

It's weird when Joaquin's interview as the freaking JOKER was not as awkward as the one in which he is himself!

[@johnnyace2287]

Kimmel was rude and not very respectful.

[@pinhead42]

Johnny Ace it was fake

[@idonthaveaname576]

The interview was a joke. It was purposely bad and awkward

[@drummer7557]

Joaquin Phoenix's actions were real, he had/has a drug issue, this was widely known for many years. Along with drinking. And the Shockumentary was NOT fake, nor was his appearance on Dave, or the weird interviews he did on the red carpet etc. He was loaded and tired of Hollywood. Also many of the scenes in the film were REAL of him using drugs etc. Hence why no one wanted to work with him or be around him for the better part of like 7 years or so. The dude is still like that today, he's not THAT good of an actor to fool everyone out there. Fact.

[@VidaAnimada]

@Alfred Person Because I have over 100k subscribers

[@jadenlaue5005]

Number 1: "Your awful Murray"

[@travisinthetrunk]

Damn! You got to it first.

[@karim-mu3xu]

"you invited me to your show to make fun of me"

[@lamanhkhoa4921]

*you're

[@abramsullivan7764]

I'm awful oh yeah how I'm awful? Played my video, invited me to your show you just wanted to make fun of me you just like the rest of them. You don't know the first thing about me pal. Look at what you did what it led to they are rioters out there and you're laughing your laughing someone was killed today because of what you did. I know how about another joke Murray? No I think we have enough of your jokes. What you get when you cross by a mental ill loner with a society that abandoned him and treated him like trash I'll tell you what you get you get what you fucking deserve. Goodnight and always remember that's life.

[@qwerttzizzi]

Maybe it was the inspiration for this scene..to be able playing the character so good

[@jocquiwilliams7635]

Nothing's better than someone passionately telling you your wrong then you prove your right 😂 priceless

[@thekrustaceox5181]

you're writing "your" on purpose right?

[@mooseidon4484]

@@thekrustaceox5181 You edited this comment for the memes right?

[@marcoramirez852]

I can passionately tell you that “you’re” wrong and no you can’t prove “you’re” right 🤓

[@jocquiwilliams7635]

@@thekrustaceox5181 I love people who proof read thier comments then edit them how it must feel to care what people think that much

[@keithmccall5170]

Jocqui Williams it was scripted. Conan didn’t just happen to have a dictionary under his desk

[@disturbedpyro4511]

I love Conan's evil laugh as he totally schools Jennifer! 😂😂

[@margarethmichelina5146]

He was really flexing to everyone at that time that he really is graduated from Harvard

[@staceyboomboom8031]

That's basic english!!!!

[@samuelgalea7679]

@@staceyboomboom8031apparently not to Jennifer

[@ArmyHumor]

Joaquin Phoenix is weird as hell, but that’s what I like about him, what makes him unique, and makes him a great actor. Keep it up!

[@sagar1589]

HE IS NOT WEIRD. HE HAVE SOCIAL ANXIETY THATS IT.

[@edybocman76]

@@sagar1589 we all had social anxiety in some point

[@jrivera018]

The guy has been through a lot in his life and he’s really shy. Any shy person comes off as weird.

[@ArkaeaFCL3]

@@jrivera018 I think its weird that we all have the same issues but we can't recognize them in other people and relate to them on a personal level. We just say "oh they're just weird."

[@jrivera018]

@@ArkaeaFCL3 i agree. i feel like i have anxiety but like someone else said, we all have it somewhat. extremely shy pepople come off as weird because they dont want to give anything out. i say they come off as weird because thats just how people see it.

[@JorikPar]

That Leno-Kimmel incident is hilarious. Not awkward, just brutally real.

[@marcelobertoni2967]

Leno freaking deserved.

[@MASTEROFEVIL]

200th like

[@vhinang-kay3037]

Satisfying actually, im on conan/letterman side. The one find it awkward and humiliating was team leno

[@shannond7437]

Jay Leno asking Kanye West if his Mom would be proud of him after the Taylor Swift incident. Number one, no question! When you have to cut to commercial because he couldn’t answer or even speak that is next level.

[@ZhangtheGreat]

Technically, that happened in prime time (as did Jimmy Kimmel roasting Jay)...

[@ReeKii]

"snuck isn't a word", please, even my 5 year old niece knows that's the correct past tense.

[@Slipknot4769]

Right? Garner is f***ing dumb.

[@electricheadboy]

Sneak, snack, snuck.

[@wednesdaywestbrook3874]

Snuck is a word. Sneaked is the preferred, but snuck is also acceptable.

[@Jedi_Are_Scum]

No one realizes that was a scripted gag?? Conan just happened to have a dictionary in his desk. Wow.

[@ManFawkes]

@@Jedi_Are_Scum there was a commercial break in between the bit. He asked one of his people to give him dictionary. Definitely not scripted

[@Yusuyusuf]

The bit with Joaquin Phoenix on Kimmel was not real, they played it, he told his sisters in a podcast you can see on youtube.

[@Andre_APM]

Link?

[@Idk-fl2ed]

@Zenzo that was the point. It was intended to be awkward.

[@Idk-fl2ed]

@MotherTouching-Ninjas you literally have the internet right in your hands. It's not that hard to look something up. And secondly... it's not that deep that someone would "lie" about it. And lastly. It's you're* if YOU'RE going to come in here accosting someone then at least spell correctly.

[@mqure1983]

@@Idk-fl2ed I heard it too. I forgot the name of the podcast. It was nice seeing him with his sisters

[@Bkk-ok2qz]

Nope that was on David letterman my guy

[@paulnieder4236]

Too much voiceover, not enough audio from the clips! Stopped watching after the 4th one.

[@C.J.Hamilton]

Paul Nieder you must be new here

[@paulnieder4236]

@@C.J.Hamilton you are correct!

[@MG-eo8ps]

She is a gospel singer, and that is her field

[@hef4x]

Shut up nerd!!!

[@paulnieder4236]

@@hef4x I'm more of a geek than a nerd.

[@nicolaspazymino7997]

Joaquín it’s not disrespectful he is just shy and humble he just doesn’t want everyone to know everything about him

[@St.Linguini_of_Pesto]

@Nicolas Paz y Mino he's always been withdrawn. It was his older brother River that helped Joaquin emerge from his shell and exhibit his prowess as a great thespian. The event that may have caused him to "hide" was River's death; Joaquin was allegedly there when River died, which was heartbreaking to hear, because they'd been so close.

[@stikvidsyt1369]

When Murray got shot on live television... Lmaoooo

[@ashutoshgarg1915]

They would surely start checking Joaquin before entering these shows after what happened in the movie

[@thedavidjscott_]

Ashutosh Garg he’s an actor not actually the joker.

[@jj7203]

David J. Scott jokes go right over your head am I right or am I right 🤣

[@sovietdeathstroke6713]

RIP Murray, hope they catch the killer!

[@muyiduyi2287]

@@thedavidjscott_ We know, he was making a joke.

[@juancruz5507]

That Joaquin Phoenix interview in Kimmel is totally scripted, what a better way to promote your joker movie than with a weird late night interview.

[@matthewviel4546]

Christ, can we hear for ourselves why it's cringey? Stop talking over the clips

[@toffeebum]

YES 👏🏼👏🏼👏🏼

[@adpiviolet]

totally agree! What's the point of making a video about the cringe moments if you are just going to talk over them and not show them!!!!

[@harmie1743]

Matthew Viel it’s watch mojo..

[@whoopityscoop5029]

THANK YOU!! I’m on #3 and all I can think is “I wish this lady would shut up and let us see the clips!”

[@RebeccaJayne5x5]

Hear, hear!

[@heyjuderabbit85]

Almost every Jimmy Fallon interview is awkward with his constant fake laughs...

[@jrivera018]

Hahahahahahaha 🤪 HAHAHAHAHAHAHAHAHAHAHAA

[@aloysschikelgruber9683]

EXACTLY

[@lando8398]

So true, I rarely watch him because of his fake laughter and fake interest in his guests

[@anthonyatkinson8545]

Thought I was the only one who thought this

[@geewiz8253]

Lando I think that’s why a lot of people stopped watching. He’s good with impressions and bits. It just sucks he didn’t get better in interviewing. It’s still awkward...

[@Akratos2020]

LMAO! the way conan was laughing while pointing at the word

[@uxwxl3332]

Joaquin phoenix and David letterman interview is legendary 😂 he fooled the entire world and made them think he's actually insane

[@arnoldpalmer1210]

Top 10 Most Awkward Moments on Late Night: Every Eric Andre interview

[@ogilvieds]

The Lance Reddick interview is a stand-out. It was staged, but against Eric so he would know how it feels.

[@kevinmurry8803]

lol

[@delloffthewall]

First, we should give a shout out to Christina Applegate

[@spittingfire420]

The T.I. one was hilarious

[@kavinpillai6515]

@Michael P yet is the best one

[@Jamesucht]

Regardless of how you feel about Jimmy Kimmel, Leno absolutely deserved that.

[@vhinang-kay3037]

I love it

[@becuzMDsaidineededpersonality]

Yes...

[@herps4life33]

He was number one and didn't want to leave lol why would he

[@Paulafan5]

9. Sarah seemed to make the interview about herself and she's clearly not a good host. Bill was just thinking: I wish I were on Conan right now.

[@ludmillagutomo]

haha..i think conan is the only host that makes him comfortable 👍👍

[@joshkanter4803]

I heard that when Kimmel started out, Leno would tell guests they had to go on his show and couldn’t go on Kimmel which explains Kimmels disdain for Leno

[@UncleEbenezer77]

Josh Kanter There's quite a bit more to it. Kimmel is a Letterman superfan, but moreso it was because Jay was negotiating his contract and ABC was interested in him. The move would've pushed Jimmy to 12:30 and Nightline to 1:30. Jay tried to buddy up to Jimmy while it was going on and when Jay re-signed w NBC, he blew Jimmy off

[@joshkanter4803]

Mike Barbas could be but I’m just writing what I have heard Bill Simmons, cousin sal, and JK all say on BS pods over the years

[@ditiromotene2582]

Conan’s evil laugh kills 😹😹😹

[@NicklePickle426]

Drew Barrymore flashing Letterman should have been on there somewhere- even in the honorable mentions! I'm 35, and even I remember that from about 20 years ago! Dave's shocked expression and red face said it all!!

[@cakeisavegatable]

That old British lady's one-liner with Mailer was so great

[@St.Linguini_of_Pesto]

@cakeisavegetable agree.. I think I saw wispy tendrils of smoke. Btw, I also agree with your user tag.. and I'd like to add that cookies are an essential portion of the "food pyramid".

[@cakeisavegatable]

@@St.Linguini_of_Pesto Why thank you and may the Flying Spaghetti Monster bless you my friend

[@jooniebear9416]

Team Coco all the way ❤

[@ludmillagutomo]

YES! 👍👍

[@xxbigbangxx1]

How the Conan-Gardner one is awkward? Jennifer totally deserved that. Making fun of someone's grammar without even knowing it properly. It's only fair that Conan schooled her.

[@digapygmy70]

I'm still impressed by Letterman not even flinching when Crispin Glover nearly kicked him upside the head. Stone cold.

[@deelee1569]

Conan's my dude 🤣

[@Jamietheroadrunner]

Conan is the entire internet's dude.

[@geewiz8253]

Dee Lee He’s the Man. The Funny Man. “The Molecular Man!” Look up molecular man SNL. Thank me later. 😜

[@deelee1569]

@@geewiz8253 I remember that🤣

[@geewiz8253]

Dee Lee You’re Awesome for knowing this! 😆 ❤️! Unfortunately, not a lot of people in my inner circle are too much into SNL. And I mean the good SNL

[@geewiz8253]

“The Moleeeculat Maaan!” 🤓 “Yeah Yeah, we know you’re Moleculo” 😂 Okay, I gotta go watch it now 😆

[@PowerGlove79]

I HIGHLY recommend watching the full Madonna interview with Letterman. It’s both of them in top form and it’s hilarious

[@talaataleghani9691]

The one with Conan and Jennifer was funniest in my opinion, mainly because they didn't seem to hate each other at the end of it.

[@rebelpunx88]

Top 10 Joaquin Phoenix interview moments

[@robinsusan4166]

rebelpunx88 Whenever I think that Joaquin Phoenix is being weird I remind myself that his parents were part of a really screwed up cult when Joaquin and his siblings were born. They eventually left the cult but who knows how much they remember from that time.

[@jessicatucker3281]

I WOULD JUST LOVE IT IF WE COULD EVER HEAR WHAT ACTUALLY HAPPENED DURING THESE MOMENTS AND NOT THE INSIPID COMMENTATOR. SHE LOVES THE SOUND OF HER VOICE.

[@maddluv123]

A good chunk of Oliver Reed's appearances on late night shows would make this list for sure.

[@mysticsaxophone4181]

He was a mean-spirited perpetually drunk man, and I loved him for it.

[@St.Linguini_of_Pesto]

@@mysticsaxophone4181 yes, he reminded me of my paternal grandmother. Makes me wonder: how great was _his_ pineapple upside cake?

[@DallasHawes]

Should’ve included Janet Jackson’s Letterman interview from March 2004... he was grilling her *unfairly* about the Super Bowl incident and it was awkward as fuuuuuu

[@stevenmattrell3448]

#1 The interview scene from Joker

[@theplayaifyer]

It starts with Joaquin It ended with Joaquin

[@blackmambagyn]

For me is the interview of Jimmy with Nicole Kidman. When he finds out he blew a date with her.

[@jrivera018]

That shit was weird. She was not into it and I think she realized how lucky she was to never have gone on that date lol

[@johncolletti]

As I remember it she did show up for what she thought was a date and as she explained “ You didn’t seem that into it .” ,because he kept playing the video game he was playing when she arrived.

[@jrivera018]

johncolletti he would have faked more laughs than she would orgasms

[@thesilvershining]

I love that interview, I watch it all the time. Every game they play and every interview after that she totally flirts with him and he’s flustered trying so hard to not flirt back 😂

[@hasansyrf]

notice there's no craig ferguson on this list because he truly is the best talk show host!

[@gillesthibault429]

"Don't touch Ivanka, she's Daddy's!"

[@akashsalian247]

all interview with lily singh is awkward worst host ever

[@Deviant69]

yeah, the talk show host gig isnt working out for her.

[@ScoobyandShaggy5554]

Deviant she will be on for 10 years or more anyways because she’s a bisexual woman of color despite the awkwardness, unless she channels in her old funny self I won’t watch

[@kenthoover7608]

Never watched her but im sure it's because she's a woman

[@iluvdissheet]

So true! I had to check when this video was uploaded.

[@shavell9447]

Who ?

[@johnny1013johnny]

I've been watching so many of these lately.. it's like you read my mind mojo

[@michaelpipkin9942]

It's like you work for mojo....

[@prismaze]

@@michaelpipkin9942 yeah😂😂

[@digapygmy70]

My dad literally told my sisters and me that "snuck" wasn't a word every time we used it. I suspect he just wanted Conan to make fun of us on live TV. Is Jennifer Garner my secret sister??

[@johncolletti]

Too much talk , not enough clips.

[@FireoPyro]

Classic watchmojo. Clickbait video farm

[@margarethmichelina5146]

Being in the talk show is like a Jeopardy on your life. It's either the host being awful to you or you're being awful to the host.

[@ingenious5480]

8:21 (jennifer and Conan) was just funny!! They both take it well

[@ghostlyarranger]

Watchmojo: "If you think that was a mess, watch the whole interview." Viewer: HOW ABOUT YOU LET US WATCH IT!

[@tenko5541]

Copyright.

[@johnfulton2672]

Spade killed it with the line "now you go"

[@ayj1166]

Ben Affleck being asked about Weinstein maybe that was very awkward to watch

[@budcooke3055]

Going to Harvard doesn’t really mean anything😂 agreed!

[@krispydream6907]

Bud Cooke fact

[@St.Linguini_of_Pesto]

@Bud Cooke very witty.. so, which community college did you waste time & money at?

[@toaolisi761]

This list is certain to get a part two.

[@donculotta1551]

The Crispin Glover interview was classic😂😂😂

[@HookedOnSonics518]

Jennifer Garner: "Snuck isn't a word." Conan: "So, you have chosen death."

[@phoenixspire155]

Jimmy how many awkward moments have you been in? Jimmy: *yes*

[@mcmandy086]

It doesn't even matter which Jimmy

[@timkinel1497]

I was surprised any of Aubrey Plaza's interviews made the cut. But it was great list!

[@Ignoremeimjustdelulu]

"what do u have them on?" omfg 😂 😂 🤣

[@ogilvieds]

Craig Ferguson and Tony Shalhoub, 5/19/2011. (The famous "Oh, hell yeah! I've got a place down there!" episode.) Craig zoned out and asked Tony a personal question about his finances. Tony was graceful, but completely shut down for the rest of the interview. He had been a regular guest up to that point, but never appeared again.

[@TheCrusader1099]

That's nothing compared to old German TV Klaus Kinski Interviews;)

[@stevemurray2040]

Was pretty awkward when Letterman chewed on Jennifer Anniston’s hair

[@CCdion23]

Conan is a class act and a legend… the other, not so much

[@spittingfire420]

Jennifer Garner trying to be smart is really awkward 🤦‍♂️😕

[@quiquaequod322]

I thought the Crispin Glover bit would be #1, but perhaps that's because it was the only one of these I saw when it was first broadcast.

[@tuph4088]

Burr And Silverman banged. I have never seen that interview before now, but after watching it for 10 seconds, they had old history, and one of them is still not over it. So much body language going on there.

[@SeymourDisapproves]

WatchMojo: *says "piss"* Me: *:0*

[@jasonmatthew5508]

It seems this channel talks way too much instead of just playing the clips. We don't need you to narrate what we are watching

[@trini4204]

Jimmy Kimmel destroying Jay Leno was pretty hilarious actually lol

[@insertaliashere1379]

Being the absolute grammar nerd that I am, I find #3 incredibly satisfying to watch.

[@Abitofeverything4]

Did Jimmy not see Joker? Murraaay literally plays a clip of Arthur embarrassing himself on live TV, then gets shot in the face lol ring any bells, Jimmaaay?

[@daveteves]

Lol you could make a whole Top 10 List just on strange Joaquin Phoenix interviews.

[@valmacclinchy]

Yup. He's hilarious 🤣

[@bennygarcia1913]

Once WM didn’t know the Phoenix interview was staged, I was out.

[@lauriwatkins4570]

Need a Part II 👍🏻

[@lotusleo1]

Team Coco reporting. Love from India Conan. Just mention of your name brings smile on my face as I start thinking about your remotes.

[@Ryanjakehenry]

To be fair, I still have literally no idea when Joaquin Phoenix is joking or not.

[@melindakinnaird]

Andy Kaufman getting punched by the wrestler on Late Night with David Letterman?

[@LordLOC]

That was a work between Andy Kaufman and Jerry Lawler. Though pretty sure Letterman had no clue about it.

[@generalpatzer6893]

Yeah that was a setup by Lawler and Kaufman to freak Letterman out and it worked!!

[@edmawhinney3564]

Drew Barrymore flashing David Letterman

[@user-ch9zq9kn4p]

Number 6 wasn't awkward at all, one of the funniest interviews ever

[@renakmans3521]

Wouldn’t it have been nice to actually hear more of these as opposed to this women...

[@Benry11_]

wish i could actually watch the moments without someone speaking over all of them

[@jsmith1746]

Can't believe you overlooked the Steven Colbert - Richard Branson dustup that ended with a water fight.

[@bluecollarmenproductions]

Jimmy ripping on Jay is fantastic.

[@mvh_1380]

I'm not watching anymore. The narrator tells us exactly what we can see/hear. What are we...dumb?!? I'm out.

[@JS-tk2co]

U can make a separate list of top 10 awkward letterman moments alone

[@forallthestupidshit3550]

You should include the clip when David Spade interviews Guy Ritchie while filling in for Jimmy Kimmel. Spade later said he thought he was being punked, it went so bad

[@LtFaceMan]

Glover's appearance was definitely more than an honourable mention.

[@Teenterror983]

I remember watching #1 when it aired.

[@margegarland7635]

You forgot when Oliver Reed and Shirley McClain were being interviewed together and David letterman interview with Jerry Lawler and Andy kaufman

[@alikatali]

Honestly, if I were in Conan's situation, I totally would do the same thing! 😅

[@1mwithnovideos289]

Everything's funny until Joaquin says.. "You're awful..."

[@bernadine6695]

Joaquin Phoenix: Wanna hear another joke Jimmy Fallon: *HAHAHAHAHAHAHA* !

[@revelore4090]

somehow I remember an even more awkward late nite interview from Joaquin Phoenix, as of recently

[@marissabones]

The awkward moments are my favourite part

[@rayo1883]

Jennifer and Conan were both correct and incorrect. There is a word "snuck" but he should have said "had snuck". People make the same mistake by using stunk rather than stank.

[@poolside123canadian7]

Madonna on Letterman better be on here.😂

[@prismaze]

It was more hilarious, flirty and kinky than awkward. There also friends.

[@poolside123canadian7]

Ian No she was stoned

[@prismaze]

@@poolside123canadian7 and that too😂. It was still funny tho.

[@MrJeparo]

You should include on the list the confrontation between Linda Ronstadt vs. Robin Quivers at the Tonight Show.

[@Coolkidcoolkid1789]

I hope I get famous enough that one day Watchmojo dissects my conversations with talk show hosts

[@Zeytrixx]

I’d be so happy to meet the Watch Mojo Lady. She has such an iconic voice. Who wouldn’t wanna meet her?

[@CoolPandaTheMovieNerd]

Sarah Silverman makes everything hard to watch

[@arrolate]

Eric Andre: Hold my beer..

[@scottstapp6763]

That crispin glover interview should be number 1

[@primeshmohanty7701]

Jimmy absolutely killed Leno!