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

[jadenlaue]

Number 1: "Your awful Murray"

[VidaAnimada]

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

[jocquiwilliams]

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

[paulnieder]

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

[shannond]

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.

[JorikPar]

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

[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!

[disturbedpyro]

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

[ReeKii]

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

[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.

[matthewviel]

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

[nicolaspazymino]

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

[juancruz]

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.

[Akratos]

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

[stikvidsyt]

When Murray got shot on live television... Lmaoooo

[heyjuderabbit]

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

[uxwxl]

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

[Paulafan]

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.

[arnoldpalmer]

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

[joshkanter]

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