Top 20 Most Awkward Moments on Late Night
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- Опубликовано: 2 июн 2024
- With great live TV comes great awkwardness! For this list, we’ll be looking at the most horribly embarrassing and difficult-to-watch incidents on these programs. Our countdown includes moments from shows “Late Show with David Letterman”, “Jimmy Kimmel Live!”, “The Late Show with Stephen Colbert” and more! Which of these made you cringe the most? Let us know in the comments below!
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#latenight #talkshows #awkward #madonna #letterman #teamcoco #kimmel #colbert 
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Which of these made you cringe the most? Let us know in the comments below!
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@@danielsantiagourtado3430 how much is watchmojo paying you
jay leno and jimmy kimmel
My biggest cringe came when Watch Mojo proceeded to voice over Every. Single. Video. You know what's good for content? Actually allowing the segment to play so the audience can feel the awkwardness without Rebecca's voice drowning out the feels
Letterman’s behavior could fill up all 20 spots on this list.
Horrid misogynist.
My first thought was, how many of these are going to be Letterman? He's the worst. 🤣🤣
That Kimmel/Leno clip was gold. Kimmel’s passive aggressive and sometimes straight up aggressive was sheer brilliance.
My favorite part was when Jay asked Jimmy if he’d ever ordered something off the TV, and he responded: “You mean like when YOU were ordered off the TV?” which was an obvious reference to Jay’s 9 PM show being cancelled. And then, as they were cutting to commercial at the end, Jimmy said- in reference to Jay taking The Tonight Show back from Conan- something along the lines of: “Why are you doing this,? You don’t need the money. You’ve got enough cars already!”
Yep, people try to act like Jimmy Kimmel was rude for doing that, but it was something that needed to be done, especially in front of Leno and his audience.
Conan went the high road, and Letterman followed suit, but Kimmel didn't care
i loved it. i was always team conan
Letterman's best line after interviewing Joaquín was “Joaquin, I'm sorry you couldn't be here tonight.” 😅😂😂😂
if david letterman's treatment of janet jackson, and so many other female guests, is him "mellowing out," he should have never been allowed on air in the first place.
I wanted to vomit and wash my own hair after watching David sucking Jennifer Aniston's hair. Ugh! 😖🤢🤮
I never knew Jimmy took Leno to task like that, gives me a whole new form of respect for gim
How can we know whether it’s cringeworthy when all we hear is the narrator’s voice?
An important thing to note about the Mailer / Vidal appearance is while the two had contempt for eachother (after Vidal made an unsavory comparison of Mailer to Manson), the two eventually reconciled in their older years and worked together frequently on stage. Two unique writers clashing on a battle of ideologies. You wont see that on TV now.
How lucky were we to witness that!
It’s worth mentioning that the “female guest” was acclaimed writer Lillian Hellman. Way to be clueless, MOJO.
@@patriciagrandjean8205 Wasn't ignoring her. My comment was specifically about Mailer and Vidal.
You're right. Ome doesn't see authors on late night TV unless the writer is a person who is famous for something else.
it's kind of fascinating how many of these see a popular host at least in some part be responsible for the controversy or awkward moment. yet Conan constantly tries the best even with guests who clearly have an issue with him.
Conan has always been, and possibly will forever be, my favorite.
I love how Conon said the word "Sneak" at 18:36. Everytime he says it, I just laugh and think "LOL" (And I don't even watch his show).
Conan was one of the original writers of the Simpsons and wrote for SNL during the late 80s and early 90s. He left SNL because he was battling depression. The creator of SNL wanted him to stay. He offered him David Letterman's spot after Dave left NBC. Conan only did audience warm-up, and never hosted anything or interviewed anyone, nor did any acting in any way. Conan knew he wouldn't get the role, but he was dating Friends star, Lisa Kudrow (before she was famous) and she convinced him to do it.
All I've learned was that Letterman was a menace!!!!
not surprised majority of the were on the letterman show
David Letterman is the center of all chaos on late night.
but he is soooo coool man
Overstatement much?
@@katica04 not really 70%-80% of the list took place on his show.
Didn’t realize many meant all
@@katica04 it's just an expression. There's no need for you to take it so literally.
Ok, so my takeaway from this list is that David Letterman was a master of discomfort. Say what you will about some of the other interviews involving Letterman on this list, but the one with Bill O'Reilly is nothing but pure joy to watch. I think that some of the times that he made people uncomfortable or grilled them on some level came from some sort of inner sense of acceptability that he felt some of them had crossed, though the Glover and Phoenix interviews were more thrust upon him than any desire on his part to create those situations.
The problem I had with Jerry Seinfeld berating the audience for laughing at Michael Richards was that he made it seem as though _Michael_ was the victim.
I love how most of them is coming from David Letterman and showed how chaotic the past was
20. Janet Jackson on Letterman after half-time show
19. Micheal Richardson (w/ Seinfeld) on Letterman to apologize for racist remarks
18. Bobcat Goldthwalt set a chair on fire on Leno
17. Dakota Johnson on Fallon tapping teeth
16. Shirley MacLaine clashing with Letterman
15. Andy Dick escorted away by security for inappropriately touching Ivanka Trump on Kimmel
14 . Guy Ritchie awkward interview with guest host David Spade on Kimmel
13. Awkward Bill Burr interview with Sarah Silverman on her show
12. Bill O’Reilly conversation about politics on Letterman
11. Trump on Colbert (need I say more)
10. Kanye West’s Jesus comparison on Kimmel
9. Norman Mailer goes after Gore Vidal on the Dick Cavett Show
8. Abel Ferrara went off the rails on Conan
7. Jimmy Kimmel mocks Jay Leno on Leno during the late night wars
6. David hounding Paris Hilton on Letterman
5. Andy Kaufman fought Jerry Lawler on Letterman
4. Crispin Glover nearly kicked David Letterman in the face on Letterman
3. Jennifer Garner got schooled on Conan
2. Madonna on Letterman
1. Joaquin Phoenix’s mockumentary interview on Letterman
This should be pinned.
Enjoyable video but how you left out the 1979 Kiss interview with Ace Frehley on The Tomorrow Show with Tom Snyder is beyond me. That is 33 minutes of awkwardness that you just cannot unsee!
I like how Leno chilled ol' Firestarter out!🤟🏿😉 Yup. Rub his nose in it!
Ah, good ol' Bill O'Liely. What a guy. He reminds me of a saying. "Some people bring great joy when they arrive. Others when they leave."
Love Bobcat setting a chair on fire Never seen Jay Leno actually get physical with a guest 😊
You missed drew Barrymore on letterman...
The list that you guys link to at the end is almost identical to this one 😂
Where is the Jimmy Fallon / Nicole Kidman interview? 😂
Jimmy Fallon and Dakota Johnson flirting was more awkward than Bobcat Goldthwait committing arson toward Jay Leno's favorite chair?
Asking Donald Trump what's his favorite Bible Verse was & he couldn't name a single one. 🤣
I wouldn’t be able to either. What’s the big deal ?
@@buddefreitas8945Ask Evangelicals.
@@user-em6ie2be7x don’t know any
Do you usually remember lines from a book you last read?
@@WahPunch Do you live your life by the last book you read?
Knowing these were all humiliation rituals is crazy to think about now.
"Even Fallon looks confused...". Have you seen his show before? That's sort of his thing. :P
A lot of people don't remember but David Letterman started out on daytime TV.
Alternative Title: Top 10 Most Awkward David Lettermen Moments Plus Extras.
This is one of those videos where it all about 90% narration.
The first one, Janet Jackson, Letterman is right. She probably wants to talk about her upcoming album or some boring thing. The audience wants to hear about the Superbowl. Letterman's instinct was correct.
Another fantastic Andy Kaufman moment was after he quit "Taxi" and went on Letterman to do a "Comedy routine" only to dishearteningly tell the audience how miserable his life is and then literally go into the audience and start begging members for cash until he got dragged out by the body-guards 🤣 The man was a genius of cringe.
Let’s face it, Donnie Donuts was probably turned on by what Andy Dick did to Ivanka.
No, he was just jealous someone else touched his woman.🤢
Hmmm from the entire vid that’s the thing that made you comment? Looks like projection
the "snuck" was awesome, don't kid yourself
Never forget that time Jimmy Fallon and Paris Hilton tried to shill their stupid monkey JPEGs on national TV, and the audience just sat in uncomfortable silence the whole time.
Ironically, if you came out of that taping with a free NFT, you more than likely still lost money.
3:12 where was he going with that? 😅
I like these videos.
I really wanted to see the awkward clips. Oh well.
Most of the Letterman ones aren’t really awkward. I can see why they’re on the list, as they were maybe perceived that way at the time, but… Kauffman/Lawler, Glover, and Phoenix are just brilliant gags. And I find the Madonna shtick just playfully hysterical. It’s like they joke about these things because there’s nothing to them. I have a friend I do that with sometimes… obviously not to this extent, as we’re not performers on stage in front of an audience. But it’s entirely playful (believe me… I’m gay… there’s nothing to my banter with my wonderful female friend, lol). So, none of these are really “awkward”. They’re just brilliant performances. And the narrator here saying that, well, Crispin Glover has never really explained it since then. Yeah, no shit. Neither did Lawler until decades later. That’s the point. Don’t EVER reveal that it was a gag. Maintain the illusion. Even if it’s obvious (the Glover one is most obvious, given that he was simply in character for his upcoming movie).
Don’t confuse brilliance with awkwardness. The Norman Mahler and Gore Vidal one… THAT’s awkward. Most of the Letterman ones aren’t awkward, they’re brilliant. They’re shticks made to make you feel awkward. And they’ve made this list some 20 years later!! Proof of their brilliance!!
Can you do top 10 episodes of Season 1 of the Stargirl TV show?
Letterman Letterman Letterman 😂
7:32 "Or they are taking the piss out of each other"... How does that work exactly?
Crispin Glover: only the first time I guess has tried to kick you? Now _that_ is fascinating.
I remember the Janet Jackson one bc it was on my birthday
LMAO poor Paris Hilton is sad.
I feel like this is the 5th time this list has come out.
One that made me cringe was when Larry King interviewed Ebert after Siskel died.
😭😭😭😭
What happened
Am I the only one that thinks the Dakota Johnson / Jimmy Fallon one was kind of adorable?
I never saw that bill burr/Sarah Silverman clip. I love them both, it's weird to see them uncomfortable with each other
Probably some sexual tension between them Just do it and get it over with 😏
Where’s Harvey Pekar’s final appearance on Letterman? All of his appearances were a little awkward, but that one ended with Harvey angrily yelling at Dave and Dave saying “We’ll be right back, and guess who WON’T be here!”
Awee. I miss Late Night..
I don't know how Craig Ferguson didn't make the list
This list is missing a very big moment - I thought it would be number 1, because there is a MOVIE about it called American Splendor in which Harvey Pekar got in a dispute with David Letterman because Pekar had a problem with GE (the parent company of NBC). The other one that was infamous for years was when Cher called Letterman an "a**hole," which is probably what Shirley MacLaine was referring to. Instead, the list includes a clip from Sarah Silverman and other clips that don't need to be on here. The inclusion of Jimmy Kimmel sandbagging Jay Leno is a bit outdated, as Kimmel has backed off from some of his criticism of Leno and the facts have shown that Leno was not "stealing" The Tonight Show from Conan O'Brien. The problem was with Jeff Zucker tinkering too much with time-slots because he thought a talk show at 10 pm would be less expensive than a drama and would get similar ratings. Zucker begged Leno to stay at NBC because Zucker was doubting whether O'Brien should host The Tonight Show when O'Brien was losing in the ratings on Late Night to Craig Ferguson. The vilification of Leno for the "late night wars" is mostly a mythologized narrative pushed by the media for dumbs**** who crave Hollywood schlock.
Surprised jimmy fallon isn’t number 1. His interview with roger waters is hella awkward
This is very awkward
Keep Trump off of all of the Late Nite Shows!!
Yes, that makes sense. Trump only brings the highest ratings to every show he's on so why would the late night hosts want that? 🙄
When Andy Kaufman and Jerry Lawler staged a fight on Letterman.😮
Can you do comic book origin of DC Captain Comet and Adam Strange?
Kanye's voice always doesn't just surprise, but *shocks* me.
Sorta like Mike Tyson’s does. This big burly dude sounds like a child. Kanye has that quality, too, but most of what he says is delusional. Jesus?? More like any sort of minor demon.
New tv list:
Shows that went downhill after a huge cast change
Grey's anatomy? Sliders (final season), scrubs,
The Conan/Garner is hardly awkward.. and not that high on the list at least :D
Bobcat rules
"I don't want to relive any of that."
"You don't mind some questions about it, though." le cringe
2:26 You left out the part where Jerry "SEINFELD" impersonating a mob boss (?) yells at Black People to just forgive his friend and get over it.
david letterman is literally the goat of late night shows
If he was "literally" a goat, he would have horns and eat his tie. You mean figuratively.
@@marcpeterson1092 No, GOAT is a new acronym that stands for "Gretaest Of All Time," often used in sports.
In defense of Letterman in the Janet Jackson and Paris Hilton clips, they do pre-interviews and discuss with producers what they do or don't want to talk about on the show. Janet and Paris (or at least their teams) most definitely knew those topics would come up and obviously didn't ask Letterman not to bring it up.
I believe they did bring it up and said it wasn't to be asked about but letterman seems like the type that doesn't really care and wants to give good TV and does it anyway.
@@jameshopkins503 No, he absolutely wouldn't. Talk shows are dependent on that trust and reputation. Letterman would've never booked guests if he was known to break agreements like that.
Surprised that Marilyn Manson didnt make the list anywhere. Letterman tried him, but kept getting out-classed
Jimmy Kimmel is the farthest thing from a comedian
Was Bobcat drunk on Leno
Most of the awkwardness on Letterman was on purpose. He excelled at this.
So madonna and Letterman is at 2, and Drew Barrymore and Letterman isn't at 1? Not even in the top 20?
Oh shoot!
Love your videos ❤❤❤❤🎉🎉
how much is watchmojo paying you
Love your spam
Not surprised most were from letterman - and the way he gets close to the female guests is a bit creepy
It would be a lot better if these clips were a little longer or showed more of what's going on.
0:59 accidentally ? They thought it would fly but people knows we get played and she saw fan said no more ... people dont like fake starz ... go keenu
The worst one was the idiot who sniffed jennifer anistons hair.
Interesting but the clips could have been a bit longer so the audience could get the full effect.
I don't think that Jennifer Garner interview was that awkward as it was funny. If I remember correctly, one of the writers was watching the feed, grabbed a dictionary, and ran down during the commercial break.
This list is a rerun.
no it not
@@jimbo9208 yeah it is. I’ve seen it many times. Good argument by the way. “No it’s not”. I hate talking to 6 year olds.
@@billythekidder7182 okay show me when they did this before
@@jimbo9208 WatchMojo does reupload videos a lot as new content, you'd have to use the internet time machine to find it.
#1 should be Michael Richards “apology” on letterman
Letterman was fun and not media trained . They’re so fake and sterile now. Telling everyone they have on “oh I’ve been a fan forever you’re amazing”. Y’all should watch how he used to roast Paris Hilton
What about all the vaccines skits? 😂
when was that
[ yawn ]
They would never put that in because they are a woke channel
@@FantaFun158Did DeSantis give you his permission to use his gimmick?
@@UncleEbenezer77 Nope, I just believe in the truth
What about the time Drew Barrymore flashed Letterman on live TV for his birthday??
Andrew dice clay on arsenio
❤ Rebeca
Poker Face 🃏
And not a single interview from Ellen's show
If janet Jacksons chest piece accidentally came off, then why was there a huge ring to cover her nipple in place?
A brilliant and awkward moment from Conan that could've made the list? Nicole Scherzinger and her breasts. Conan handled that amazingly!! 😄👍
So mostly letterman
Ugh I cannot stand Phoenix
Ummmmm, Farrah?
Letterman RULES!
What I love about MOJO is that they continue to believe we would rather hear then yap than listen to ANY of the clips
If they'd actually play more than a minor snippet of a clip.
More reasons why I am not a fan of Letterman.
No Tom G with the cutting of the desk? Or Opera and Tom C jumping on the chair? Or John S asking Reggie M if he can dun when he sat that time was the most prolific 3pt shooter. Ext. so many missed opps. Do a pt 2!!!
Find it annoying that these clips are monologued with a voice the whole time. Would rather just see the clips
Janet did not deserve that Justin got nothing it was a accident period