MADONNA/ ON DAVID LETTERMAN SHOW/ 2000/ PERFORMS DON'T TELL ME/ THESHOW 2019/

This was the era I liked best of Madonna. When she was in her 40’s. The Ray of Light, Music, American Life and Confessions on a Dance Floor albums. Her kids were children at the time and she was married. Maybe all of that gave her some groundedness.

I lucky enough to get tickets to Letterman this particular night. I was on vacation in New York City to see the Rocky horror picture show live on Broadway! Starring Joan. Chad and Dick cavett and a fantastic troop of players. And I just happened to manage to nail tickets to Letterman which they record at 6:00 p.m. or they did at that time and it left just enough time to grab a drink afterward and make my way to the theater. It was the spectacular evening. I didn't know at the time that Madonna was going to be on Letterman that night. I just booked tickets because I was able to get in and I thought it would be fun. During the commercial breaks she was hilarious. Her and David went back and forth and it was just so much fun that entire evening was busy and just absolutely as much fun as you could have in your life seeing Madonna and then Rocky horror live on Broadway and then going out to a few bars. What a wonderful night!

I miss this Madonna.♥️

The way she just sees through his shit the whole time, inspiring man

Admit it, we ALL miss this Madonna.

Madonna's giggle has always been so infectious 😄

I can seriously respect this madonna performance, shes singing and playing guitar with no back up! That's unheard of these days, she sounds great

What a treat to see Madonna play acoustic guitar and accompany on vocals

You can debate about Madonna all day, but the bottom line is the key to her success has always been her ability to craft memorable pop songs.

I’ve never heard this acoustic version – just raw talent: Voice, guitar playing, songwriting - impressive and simple at the same time. Great lyrics, too ✨

no music female icon will ever compare, she IS the standard. and the Music album, 20 years old? ahead of it's time, as always.

Whoever said madonna couldn’t sing? Madonna’s good at all parts of the biz. Love it.

This woman is the walking, talking definition of cool. Nobody intimidates her. Fuckin love it.

This performance must have been nerve wrecking for Madonna... She obviously felt vulnerable and insecure, albeit she did it! Pure and uncut, I love and miss this Madonna <3 #Queen

Watching Madonna on the David Letterman Show over the years has always been fascinating. The back and forth banter and interaction between them is full of wit and is really funny. Letterman likes to bait her to talk about personal stuff and controversies but she’s learned from previous experience how to parry them and turn the questions back at him. But through it all, they appear to have developed a genuine respect and appreciation of each other. No nastiness or crudeness here, just two intelligent people entertaining their audience. Madonna was gracious and Letterman obliged her.

I've watched this interview so many times over the years. I still think it is one of the best she's done. Madonna went from here to Ray of Light to Confessions. She looked and dressed fantastically. She was living in London with Guy and her style became more subdued and European chic. Far and away my favourite Madonna period.

I get such a kick out of her. She’s so confident!!

Say what you want, she has smarts & talent. She choreographed much of her own shows.

I want this Madonna back 💔

i love how Madonna's personality changes with each album ( she just evolves -grows) and i guess so do we All :)!