“Unstoppable force vs immovable object” energy 🤣🤣🤣

This was a huge pop culture moment at that time. The cursing and vulgarity was something you didn't see on a show like this. Now...well, it wouldn't even make news.

I was at this taping. It was a great moment. During the breaks, they were still telling jokes. This was one of the best Letterman’s interviews.

This would never happen today. Late night talk shows are so scripted and safe and BORING.

“What is that? A swim cap…?” Freaking GREAT comeback!

I still laugh out loud at this interview every single time. A superstar being so chaotic on live tv back then was so wild, iconic.

All I can say this is the legendary interview, the interview that cannot be happened today. They both maintained their own wildness of 80's - 90's, and decided to crash as hard as they can. Witt, humor, bravery, assertiveness and intelligence exploded all together in this interview. While some celebrities got publicly humiliated by David, not having a chance to fight back, but Madonna, she was never one of them.

Do you get the feeling Madonna had the time of her life? She really had a good laugh, as we all did. She couldn't stop giggling.

I remember this interview from back in the day. Madonna was all over the news because of what she said and did in this interview. If I remember correctly, this was one of the most popular reruns of Letterman well into 1995.

I remember this so vividly. I was in a friend's dorm room. I watched Letterman every night in college.

Madonna has always been notoriously hard to interview, Dave being the absolute professional he is manages to just keep it going and we have a classic episode!

Dave was incredible the way he held his composure and harmlessly fired back at Madonna in a friendly way. Not easy to do...

"That microphone is really long.... Speaking of the NBA." 🤣🤣🤣

She was onto something. Her chaos and confrontationality in this interview were piercing a hole in the polished, be-happy, look-nice veneer that was (and still is) talk shows

He's pushing her to kiss a stranger when she doesn't want to and he's calling her inapproperiate for saying cursewords. aight.....🙄

This interview is iconic at this point. Never have we ever had a superstar as fearless as Madonna especially back then. Legend!

The payoff to this came at the MTV VMAs later that year. When Dave and Madonna showed up on stage together, the roof blew off the dump, to borrow a favorite Letterman phrase. And, of course, Dave delivered his line - “I’ll be in the car. Watch your language” - PERFECTLY. What a performer. What instincts. This is why Dave is iconic.

People don’t understand just how talented Dave really is, it’s extremely hard to do what he does on the fly 😂

“What is that- a swim cap?!” 🤣😂🤣

2 heavy weight champs sparring and it’s amazing. Dave’s comebacks are lightening fast. Most talk shows are soooo boring now. This was truly epic.

Dave has a perfect comeback to any situation as fast as a bullet. When Madonna turn to the guy "who said that?" got an instantly "he is the guy you didn't want to kiss at the begining", that was very fast.

Madonna being high for the whole interview was an iconic thing in itself 🥰👍🏻

I remember watching this in Australia and howling with laughter so much i got in trouble with my folks haha

I remember watching this with my Mom (I was 14 at the time!) she and I both were shocked and laughing throughout the entire time! (especially when they kept cutting to the old couple in the audience!)

This was so great! Only Madonna can take over the show and only Dave can handle this interview. The two of them going back and forth was like two prizefighters. Just classic!

Dave put on a masterclass in dealing with a complicated interview.

Paul jumping in with the Tonight Show theme was genius.

One of Daves best interviews. I absolutely love his sharp responses. He is just not impressed by her remarks. Who else is that quick?

I used to record Letterman and watch it with a few high school friends during lunch hour in the art room, and we watched this a few times - it made the morning news, and we were so excited to see this.

I've never been a fan but she does have attitude. I'll give her that.

Robin Williams described this as " a battle of wits with an unarmed woman "

Okay but can we appreciate how good Dave handled Miss Madonna and had the funniest comebacks instead of getting offended and stopping it THIS IS HISTORY

This never gets old, funnier than hell!

This is the best interview ever…the chemistry whatever it is was awesome and natural

That was one of the wildest, most off the wall guest appearances that I have ever seen!

Dave: "We wanna get the Counting Crows out here to play their songs." Madonna: Why?

It's like a complete train wreck and a brilliant live comedy show all at once! Hilarious and deeply uncomfortable but you don't want it to stop 😆 Dave did a sterling job of holding his own against her, they have a weird and explosive kind of chemistry together. Deep down I think they really do like each other.

Didn’t see it live, to my own chagrin. I had to wait until KZfaq years later to finally watch in its entirety. Even then, it was a renegade video: back when KZfaq kept everything under 10 minutes, so you knew it would get scrubbed. Dave was so damned professional and hilariously still Dave the whole time. Magnificent.

The swim cap comment got me crying 😭 he was eating her up 😭

One of the most legendary interviews in late night ever. Love it. Beautiful Johnny Carson reference at @17:30 from both Dave and Paul who spots it immediately and starts playing the theme from The Tonighr Show.

"Former mayor of New York.....Dave Dinkins?" 🤣🤣😂😂🔥

PRIME Madonna! PRIME Dave! God, that was freakin' fantastic. We're talking 28 years ago, and I remember it like last night. this is SO FUNNY! What chemistry they have.,

Only Dave could have handled this interview so well

I remember this. It was hilarious. That was also the third time that grocery bagging champion got bumped. He came back in a later episode and talked about meeting Madonna in the green room.

A classic interview. Should have included Dave’s intro: “Our next guest has slept with the biggest names in the industry,” And Paul’s astonishment “She your guest!”

Madonna was so fearless wow. The back and forth between her and the host shows maturity that she can take a joke and she wont just sit , she will also throw the punches

That old dude was legit disgusted 😂

The only late night host that could handle her...he's a legend

Easily the best interview of all time. I heard humours that at the time the latterman show was struggling for ratings and David latterman asked Madonna to be outrageous and wild prior to the show started. Madonna was dating Tupac at the time and she admitted on the latterman show In 2009 that she had a joint prior to the show. Madonna even asked Dave “have you Ever smoked Endo? So basically she was high lol!! No other music star could cause such controversy then Madonna. No way she could get away with it now In 2022 as people would be too offended. Especially in the day of social media. It would ruin her career. This show is still the highest rating episode in lattermans career and Madonna’s single I’ll remember after the show aired peaked at No.2 on the billboard charts for 4 weeks. So it worked out well for both I say

this is the most entertaining yet pointless interview! great stuff

Madonna admitted later she was high during this interview (obviously).

She was 36 here. I thought she was like 44...

I remember watching this Live, and had been Lucky enough to have taped it so I then was able to rewatch it again and again- Dave is a Legend, but one of the things Dave could do so well is when a guest goes off kilter, the interview starts to go wrong, you see Dave's face and attitude just go "screw it", he starts jabbing back, and somehow he and the guest end up having a great time- Madonna was one, the Andy Kaufman/Jerry Lawler bits, when Joaquin Phoenix went method actor, and all the Charles Grodin appearances (that was an act, but I never knew for years- Grodin and Dave played off each other so well) - I remember when there was an older Lady who had an "act" with monkeys- they went crazy, and one was a Baboon and Lunged at Dave- Dave was genuinely afraid but still popped Lines and made comedy out of it

Classic and completely iconic till this day. I hope they upload her follow up interview with him in nov 2000. Complete night and day! Dave why haven't you had her on your Netflix show yet?? Long-overdue

I remember watching this when it originally aired. I was a junior in high school at the time.

This feels chaotic in 2023…hard for me to imagine how it seemed in 1994…

This interview was so controversial at the time. I remember news programs saying that this interview had the most "bleeps" at the time. When Madonna and Dave showed up together at the awards a short time after, it was classic. =)

“Dave you are a sick fuck!” Band: Plays Holiday😂

She is high asf here. She was dating Tupac at this time and just got done "hanging out" in the back with him 😂.

Back in the mid 90's I was Leaving Webster Hall Madonna got out of her Limo and walked towards to me and bumped in to me and smiled...I turned around to look at her and see continue walking into Webster Hall. That night I didn't know that was her until the following day to later found out Madonna was promoting Pajama Night Party and her new album.

I know there are a lot more obvious things going on in this video, but can we take a moment to appreciate how at 17:33 Dave does his Johnny Carson impression, and almost instantly Paul Shaffer starts playing the Tonight Show theme?

There is a magic in this interview which i really don't see anymore. Late Show was a party every night no matter the guest.

Its charming to see her so self-conscious.

"I can't, he's not tall enough." Story of my life.

Classic! Best talk show interview / banter ever!

This is amazing! What a gold moment for pop culture. Madonna was so fearless and having so much fun and Dave was enjoying so much, following the acid mood of the talk all the time. She was so ahead of her time (even now a days) and its really good to see moments like this. So sad the tv and pop artists became so plastic with time.

Legendary interview

You did have something there, David Letterman. One of the highlights of your show. Ever.

Wish I could go back in time capsule. Watching this making me feel nostalgic. Loved 90s Madonna

"You realize that this is being broadcast, don't you?" - "Yeah, you realize that I'm Madonna, don't you?"

7:54 you're welcome!

16:30 "It seems like it has" 😂 I STILL remember that comeback. This interview showed me what a pro Dave was.

This what she would’ve looked like if she’d done The Matrix. She was offered the role as Trinity but turned it down!

I’ve never seen Letterman as genuinely angry as when she started swearing.

This is the first ever episode of David Letterman I ever saw - watched it with my dad on vacation. We both thought she was bonkers but I loved every second of this mess. Letterman was the best.

I remember watching this first air as a kid. I didn’t get a lot of it but the swim cap joke made me laugh hysterically.

In a different way clichéd and obscene, but at the same time the best Letterman Late Show that I have ever seen.

i've seen this too many times and i don't plan to stop 😂😂😂

madonna was going to the free fall part of her career, but she made "rain" which made her ok again until her latest stuff which is nuts. She's had a great career.

Can understand why her first marriage lasted as long as it did after watching her here.

Two entertainers at the top of there games. Two very different games, but both charming in their own way. Dave is always Dave, but finding Madonna that attractive just shows, I've definitely got a type.

Dave is sharp as hell with his comebacks. He put her in check multiple times! 😂

I really miss her being like this. She’s so jaded and hyper-obsessed with youth that her amazing talent is overshadowed by her desire for relevancy. I wish she would have taken the higher path and aged with her dignity still in tact.

old but gold. they both are Funny and Freindly..lovely ínteraction :)

People were mad about this but she gave that show life and reality that night I love her for that. Dave really did a great job rolling with the punches as well

This was when Madonna had her New York accent. Six years later, she moved to London and magically picked up an English accent.

"Is that a swimming cap" 🤣

I never cared for her or her lousy songs. But shes smart she knew how to get attention and made millions doing it.

"What is that, a SWIM CAP?!" Dave Letterman was so quick.

The one time when David Letterman was completely upstaged, taken aback, dumbfounded and IMPRISONED! A moment in television history that will stand as an indestructible monument!

I remember watching this first time on weeknight late show with david. Time flies.

This is pure gold!🥲

And then HUMAN NATURE was born!! The backlash she received from this interview surely inspired her songwriting

Love, hate, or don't care about her, she really was far ahead of her time - for a very long time. Gotta give her credit for that. These off the rails episodes are incredible.

seems like Madonna has a mad crush on letterman.

If this is a contest to see who was the smarter, wittier, and funnier of the two, the obvious victory goes to Letterman. With his comedic-improv-standup skills, he schooled her on how to give a snappy comeback. All Madonna did was cuss and try really hard to look like a bad-ass, which was pathetic and sad. So Dave wins this handily.

I love Modanna. Subverting everything with no apologies. Dave riding through, but it ended with a great laugh.

Fair play to Madonna for trying to break the system and fair play to Dave for his professionalism 😂👑 legends

Her laugh is so cute. I think she had a little crush on Dave.

14:12 This is quite a brilliant moment. It seemed she broke character when he said that he knows everything there is to know about her. It negates the whole act. And she replies that he doesn't know a go**** thing.