“Unstoppable force vs immovable object” energy 🤣🤣🤣

“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.

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 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 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.

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

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

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

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

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!

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.

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!)

“What is that- a swim cap?!” 🤣😂🤣

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

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!

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

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.

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

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.

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

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

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

This never gets old, funnier than hell!

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.

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

Paul jumping in with the Tonight Show theme was genius.

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.

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

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

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

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.

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

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

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.

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.,

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

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.

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!”

this is the most entertaining yet pointless interview! great stuff

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

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

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

Didn’t see it live, to my own chagrin. I had to wait until UKposts years later to finally watch in its entirety. Even then, it was a renegade video: back when UKposts 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.

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.

Classic! Best talk show interview / banter ever!

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

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

Legendary interview

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

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. =)

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

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

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

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?

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

"Is that a swimming cap" 🤣

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.

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

That old dude was legit disgusted 😂

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

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

This is pure gold!🥲

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

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

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

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.

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

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

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.

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

Awesome 💯

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

The Sandra Bernhard/Madonna tag team with Dave was epic in 1988 (I think).

"See I haven't dated that many basketball players." Never noticed that before!

this is amazing

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.

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

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.

18:27 she was actually angry

love how classic this feels like smoking cigars on live TV no taboo topics actual charismatic interviewers & stars like this was rlly the golden age of pop culture. also random but the ad placements at the original commercial breaks >>>

Dave is a legend. Good night everybody

As per usual, Ms Madonna was trying to take the center stage. She just brought out the complete narcissist in her. It was nauseating. However Letterman's responses were great. He's still the man.

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

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.

I was in South West Africa serving the balance of my 2 year military conscription when Madonna really started hitting the international chart's her music was inspiring and uplifting with an essence of raw energy, a yellow sony portable tape deck with headphones this tape and a few other 80s inspired music/ moments took e out of the present moment and into a possibility/inference ...at that time she was my true blue ...

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.

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!

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

seems like Madonna has a mad crush on letterman.

Dave is brilliant!

The funniest Madonna interview of all time in my opinion. I think that Madonna and David Letterman like each other and have since moved on from this interview, but even during her later David Letterman interviews David almost always makes references to this interview.

I love her giggle

What is that a swim cap?? 🤣🤣🤣🤣🤣🤣🤣

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

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