Top 10 Most Memorable David Letterman Moments 

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Letterman is a living legend. There will never be another like him. He definitely raised the bar!

"Joaquin, I'm sorry you couldn't be here tonight." - The Best Ever

I miss this show. Basically fell in love with it growing up having no cable and it was the only clear channel to watch on the local CBS. 🤷🏿‍♂️😂😂

My very favorite DAVID LETTERMAN SHOW WAS THE ONE WITH SONNY & CHER on it and their now son Chaz but was then Chasity sat in first row. David got them to sing "I GOT YOU BABE", which left CHAZ IN TEARS AND some in audience in tears as well! It was an absolutely amazing, monumental moment that captured the special magic that was Sonny & Cher! I will never "EVER" get sick of seeing this particular episode nor will millions of others! Reuniting and singing "I GOT YOU BABE" is perhaps the best episode of any program then or "NOW!"

I was actually in the audience on set for the Drew Barrymore episode. It was Dave’s Birthday. Rudy Giuliani, and Luciano Pavarotti were also guests. A couple friends were at the show the night before and were brought up to Dave’s office for stand in day and they had Wolfgang Puck cook for them while they ate with Faye Dunaway and Barry Manilow played piano for them. Unreal right? I couldn’t believe it. Then I get to experience one of the most famous and iconic episodes in person the very next night. An experience I’ll never forget.

I miss Letterman soooo badly. Nobody will ever be able to beat him or Johnny Carson! They are the the GOATs!

Letterman was the king when it came to how to handle dead air.... when his guests said something inappropriate or outrageous, then followed with saying nothing, the whole world couldn't help but laugh at Dave's physical comedy...his facial expressions revealed precisely what anyone would say in those situations, without speaking a word...his timing...impeccable....he took the Late night talk show format leaps forward, to the world's benefit....just genius.

There will never be another Letterman. Thank you for all of the laughs!

The GOAT. Not only THE greatest late show host but also one of the best comedians.

I miss watching DL. I used to watch almost every night. The good ol days.

In 1981 I couldn't stand David Letterman,......The years went by ,and AFTER his major,major By-pass surgeries,emerged THEE David Letterman that (after MANY,many yrs.) I finally loved and FAITHFULLY enjoyed. His comedic GENIUS blossomed!!!.,.......Paul Schaefer and the A#1 orchestra was a HUGE "cherry-on-top".This combination I (IMAGINE) think will never be duplicated.,....,There's No-No late night TV to match that ERA.But the trade-off is getting to bed at a decent time so now I enjoy the PRE-sunrise hours with much enjoyment.,......,....With all "RESPECT" to Letterman & the orchestra& FANS,The "2nd" half of Dave's (in my honest opinion) TV-Life was spectacular.,........Thanks to Dave,Paul & the real professionally trained and schooled musicians.A true slice of American HISTORY.

As a teenager, I used to stay up to watch David Letterman on the late late show which started at 12:30pm. Excellent television.

"I'm gonna go check on the top 10." Just...perfect.

Letterman was the man. He had great chemistry with many guests.

That Madonna interview is ICONIC!!!

"Joaquin, I'm sorry you couldn't be here tonight." Hilarious!

Crispin Glover was in character for a movie during his interview, and he never broke the act. Gotta give him props for that

Love that Kauffman & Lawler is still seen as real to so many people. Both amazing men

I can't understand why Cher didn't make the list. After turning him down for interviews for years, she finally went on and told him SHE called THEM and agreed to come on if they would pay her hotel bill of $20,000. She had been living in a hotel after leaving Sonny but couldn't afford the bill at the time. So she let Dave know quick that the only reason she was there was to pay her bill. And they agreed to pay it. She thought he was an asshole. Afterwards, they apparently became friends and she did his show several more times.

Sonny and Cher being goaded into singing "I Got You" impromptu was my favorite.

David is a good example of a man who knows how to approach any situation.

Drew Barrymore flashing Letterman. The freeze framed look on his face afterwards: priceless. I rememeber seeing this at the time. It would have been 1995.

He was touching and perfectly professional after 911. Bless him. And it was the greatest compliment for Carson to make his last tv appearance on Letterman!

David Letterman is a legend.

Top 10 David Letterman Top Ten Lists

He is so much better than any of today's hosts. Great show and very much missed.

Letterman and Carson are untouchable!

Drew flashing Dave was one of the best moments...totally awesome!!!

Go to 9:30 and it totally looks like Joaquin Phoenix is the one saying "and".

His 'in memory of' calvert deforest (before he died) where he comes out later on to say "I'm not dead you bastards" will always be a top 10 to me.

Carson and Letterman were great talk show hosts. I sure miss seeing them.

THANK YOU GOODBYE AND FAREWELL TO THE LATE SHOW WITH DAVID LETTERMAN 1993-2015

Loved Letterman. Greatest of all time, period

We seriously miss you Dave!! Thanks for years of laughs😁

The "I'm sorry you couldn't be here tonight" line might be the funniest thing I've ever heard Dave say

After Andy Kaufman passed away Jerry Lawler explained that everything they did was a "work" meaning it was pre planned. Originally they were both supposed to apologize and sing "What the World Needs Now Is Love Sweet Love" but the feud between them was drawing so much money that they didn't want to end it. According to Lawler, slapping Andy was Kaufman's idea but they didn't tell Letterman so Dave's surprise was genuine. Kaufman, who understood the wrestling business, signaled to Lawler that he was going to throw the coffee by grabbing the cup and then pausing as he looked Lawler in the eye. Lawler understood what that meant and it gave him time to move out of the way and when Andy threw the coffee he threw it behind Lawler hitting the empty chair. There are several videos that are easy to find of Lawler telling the story of the feud between him and Andy and they were actually good friends who shared a love for the wrestling business. Kaufman had everybody fooled and at one point he scared the daylights out of management at NBC when he threatened to buy the station and turn it into a 24 hour wrestling channel. Lawler and Kaufman created one of the most controversial, entertaining, and lucrative feuds in the history of professional wrestling and gave me a new respect for Kaufman as a comedian as he managed to pull off what may be the greatest wrestling / comedy gag of all time.

13:47 This moment cracks me up every time

No final stand up from Norm Macdonald where Norm cried? That was heartwarming.

You missed one that, for a short time, caused an international incidence! The former Soviet Union was having a food crisis when their crops failed. (I really do not fully remember all of those details). I do remember that at the time, the US was sending a cargo ship loaded with grain to help them. AND I very well remember Letterman calling a representative of the USSR on his show LIVE!, (the then Ambassador from the USSR perhaps?), and him talking about how great it was that they were helping their "Cold war" enemy. Then, just as he was hanging up from the call, Dave added almost like a quick afterthought, words that basically said, something like, "Oh, and we've poisoned the grain"! Well, his "funny" little joke, did get a reaction, but perhaps not in the way he would have preferred. His remark caused a huge stir between the USA and the former USSR and Dave almost got his show canceled. I was watching the show that night, so I KNOW that this happened, but I have never been able to find out more about it, or a video replay of it. In my opinion, that is one of the hugest "memorable moments" from the Dave Letterman show.

His final episode should now be included in this. That Everlong montage thing happening was a tear jerker!

"You're putting words in my mouth, just the way you put artificial facts in your head." That is literally the BEST insult someone could throw at Bill O'Reilly! #thanksdave

This man is the king of sarcasm. Love it!

Bagging Johnny's last appearance before he hit the links for good should have been higher. Dave's a legend, too.

Lawler and Kaufman without a doubt should be number one.

The all-time winner for me is a vanity at the end of the show showing the CBS logo, with a voice-over saying "ooh, it's that creepy eye!" I never laughed so hard....

Sonny & Cher should be #1, Can't believe it was left out.

Cher calling Dave an asshole from 1984, and the blunderous first Marylin Manson appearance in 1996! Crispin Glover, Farrah and all of the Andy Kaufman, Bill Murry and Howard Stern appearances are gold!

The one that was most memorable for me was the reunion of Sonny and Cher.I know there were so many memorable moments, it would be impossible to show them all...Good list btw!

I will always remember a series of events back in 1985 or 1986; Dave had on "The Worlds Fastest Hypnotist" (I think his name was Marshall Silver), and while the guy tried to hypnotize an audience member, Dave mocked him mercilessly. A couple of days later, they had to have him on again to attempt to hypnotize people because the dude threatened to sue Letterman. A forgotten but bizarre series of events on Late Night.

David Letterman was my bedtime story ❤🎉🤟😎

The Cher 'asshole' interview was pretty good too. And Sandra Bernhard "And one of them's got YOUR name on it Dave!"

The Paris Hilton interview was classic. 😂

That takedown of Paris Hilton was brutal and completely necessary. Thank you Dave!

I REALLY HAPPY TO WATCH THIS MEMORY RU-vid ESPECIALLY Mr. DAVID LETTERMAN THANK SO MUCH FOR YOU

Dave is sooooo smart. And landing Johnny... That was maybe a statement of how late night should have gone. Love and miss Dave. Best latenight guy ever.

My favorite Letterman moments were his interviews with Hunter S. Thompson and Harmony Korine. Korine actually admitted to being high during his interviews years later.

His interview with Oliver Reed in 86 or 87 was another classic

My roommate’s mother was David Letterman’s high school English teacher. Three memorable Lettermans for me, REM, Imitation of Life, just before 9/11, the 9/11 show, his return after bypass surgery.

“What are you doing here? I thought you were dead!” IM DYING!!

letterman is by far the most fearless late night host of all time.

i like the one with harmony korine, pretty bizzare and rude, as he is to most of his guests. :)

I was literally rolling on the floor laughing when the show with Paris Hilton aired. I almost felt bad for her, but she was asking for it.

I saw all these growing up. What a trip to memories of being a teen for me.

Norm MacDonald's last standup on Letterman is #2 at least

Best talk show host ever

Happy 75th Birthday David Letterman

I see David looked at Joaquin's beard and thought I will have that lol

Am I the only one who thinks joaquin Phoenix looks a lot like zach galifianakis

Other memorable personalities from Late Night With David Letterman from the 1980s I enjoyed were Chris Elliot and Larry "Bud" Melman. Dave had some great eccentric people on that NBC version before he moved on to CBS.

Number 1 should have been the speech he gave about Robin Williams after his death. Dave was heartbroken, they were true and dear friends. Everything he said came from his heart, Dave poured his guts out. Very raw and real. This video should be re-edited to include that.

Good One. I used to watch and enjoy David's Show often. Thanks.

The Andy Kauffman moment still up there on any late night or tv list.

I am not from the USA but I know what a legend this man is. Even if you don't like the show or his style, you got to have respect for him. For so long hosting a late night talk show and becoming such an icon. Yeah, he's a true legend for all of television.

I watched this show religiously. Amazing how many of these I saw when they originally aired.

Letterman is special to me! Used to stay up with my grandparents to watch!❤

You forgot to mention the time Dave interviewed Hunter Thompson form his hotel room across the street because he refused to come to the studio .Dave got a camera crew and filmed the entire show from Hunters hotel room

One that stands out for me was when Tom Hanks was telling a story about Slappy White. "Stop bending the shaft!".

Chris farley's interview, where all he kept saying was yeah....lol

I actually loved Dave with Richard Simmons..Those two together was golden.I never laughed so hard way David acted towards him it was the best!

This was a good list, but Warren Zevon deserved #1. His appearance and performance were breathtakingly honest.

watchmojo aren't even scraping the barrel anymore, they're inhaling fumes from it.

I wish the list stuck to comedic/zany interviews. 1) Crispin Glover's return visit was a hoot... 2) Jennifer Tilly appeared to be on speed, rattling on, not letting him complete a sentence. She got ultra crazy when Dave slipped up and referred to her as Meg (her sister). At one point Dave admitted that she was beginning to scare him. 3) Letterman's time with Michael Keaton was a riot. Dave asked him how it was to work with Dana Delaney on Batman Returns (she wasn't in it). A recording of Bud Melman constantly asked "Is Batman here yet? I must speak to Batman!" from inside a drawer in Dave's desk. Keaton poured his beverage into the desk... 4) During Cher's 1st visit she told him that she waited years before coming on the show because she thought he was an @ssh0le... I taped maybe a couple hundred episodes in the 80's & 90's.

One if the GREAT shows of television.... never to be replicated.... thanks Dave :-)

"I'm sorry you couldnt be here tonight " omfg I'm dying ..

i was hoping one of them might have been.... sonny and cher reunited , dave made her sing...we had "ive got you babe" omg, it was so great !

Used to love Late Night in the 80s....after working the 3-11 shift....smoke a joint and have a few laughs.

The thing about Drew Barrymore 's flashing Dave is that it wasn't seduction or vamping....it was dancing and an impulsive flash by a very sweet person. She seemed as surprised as Dave that she did it.

I think the Chris Farley entrance to his show should’ve definitely been in the top 10.

Andy Kaufman... The man was/is beyond amazing...

That Kaufman Lawler spot was just TV on 10. Great stuff

Great list of Top 10 Moments on Letterman except for 2 omissions: Final appearance of Sonny and Cher and Dave wearing the Alka Seltzer tablets in water tank.

I wish we had great Late Night overseas like this. Letterman, Conan and such are legends and I'd watch them everyday. To be fair though, America has a huge amount of top list celebrities to invite to those shows and not just boring-ass pseudo-celebs who just wanna sell their books and the showmaster won't even ask questions but just not and say "Yes".

In case you were wondering how the Mojoholics voted in our poll, see the votes and entries here: www.watchmojo.com/suggest/Top+10+Late+Show+With+David+Letterman+Moments Note, of course, that viewer votes are just one of the hundreds of data points and variables that we consider and look at when we create our lists. Make sure to sign up and participate on future lists at www.WatchMojo.com/suggest

Definitely Joaquin and Drew's my favourite moments!

When Norm Mcdonald teared up on the last show that to me belongs in the top 10 Letterman moments.

Maybe do a Top 10 anti-pirate traps in video games. :P Things that pirated versions of games do to make them impossible to beat/play.

Real tv legend. David Latterman was truly, one of the big mans.

not sure why Warren Zevon - "enjoy every sandwich" was not in the top 10, it's by far the most profound moment of the show

Incredible Letterman...