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!

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

I miss this Madonna.♥️

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

Madonna's giggle has always been so infectious 😄

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

Her acoustic performance was great, I loved 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

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

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

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.

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.

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

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

I've watched several Madonna videos today...I never knew she was so giggly. She has a wonderful full laugh, and it's very infectious! I laughed too.

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

She is so Full of Innocence, Wits , Creativity and Life! Gosh!! I only knew her through her song "Frozen" and nothing before or after that song! But looks like missed such Diva!!! Mind Blowing!!!

Ray of light / Music era was the best! 2 Of the most iconic, legendary albums of all time back to back!!!

I want this Madonna back 💔

Madonna was at her best here. Gorgeous and at her musical best.

21 years later, it is difficult to imagine the stir this lady Madonna caused in the world.

Her voice is so melancholy and complements the sad lyrics. Second time I've listened to this song and I appreciate Madonna more now than ever.

It's difficult to express just how amazing Maddona is here singing and playing guitar at the same time.

Her voice isn't spectacular like other singers but it's massively iconic. I hear it and it's unmistakable and conjures up my time as a young person in the 80s and how iconic she was to the Era and for women.

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

Admit it, we ALL miss this Madonna.

What a great interview..and beautiful song with acoustic guitar! Probably the most vulnerable I've ever seen Madonna, in the best way possible. 💖

This clip shows why she's been so successful and lasted so long. She has musical talent and the ability to write and perform a memorable song.

Madonna was her most beautiful from 1999 to 2006. She looks so gorgeous here. I wish she would have just aged natural. She would have looked SOOO amazing just aging normal. But I love her song "tell me love isn't true" and also "musicccc". I can't remember the names to those songs but late 90s and early 2000s Madonna was the best! She looks beautiful with minimal make up and blonde hair.

She's matured up and come into her own here.

I love that song and the guitar playing was perfect. She sang it like a true Rockstar.

Her performance was beautiful

This woman literally changed AND saved people's lives, including mine back in the 80's, and I don't think she realize how big an impact she has on people... 👑💋❤️

This is such a lovely interview .. and her performance was soothing

Such a full conversation. Two people who totally misunderstand each other. But by the end Madonna gets maximum respect.

She sings live and without the backup singers…and the rawness of her voice sounds good!

Wow Madonna can sing! I LOVE HER!! Didn't care how she pulled it off. This is one of my favorite songs of hers. Adore this version. Now I have to go watch the video, which is awesome probably why I love the song so much. Was living in Vegas,had a break 💔 up. Seeing her kick up dirt and men worshipping her(when I had TONS of attention too) I loved her fighting for love. Best interview with her I've ever seen.

I can watch her talking whole day. She is absolutely charming and amazing.

Go listen to her "Music" album from 2000. Its literally just as relevant sounding today as then, its amazing how forward thinking she is

I think this was Madonna's cutest stage in her life - cant get much more than this.

I love that she kept the guitarist even till now, he is also amazing musician

I liked her so much better when she was this age at this time in her life she was personable and funny and lighthearted.

Let’s just say Madonna was a great guest in every aspect. Could stand up to Dave and anybody she faced. Just always loved her…

21:00 she plays acoustic wonderfully and her singing on this is way better than the recording!! So new and fresh if you haven’t heard her sing this tempo! ❤❤❤❤

I love Madonna in all the era’s she has gone through. Through her worse times to good time. I guess I am just a fan. She is a music legend, one of a kind.

Madonna was terrific on the guitar and she looked great too. I liked this interview.

This is where her career should be going in 2021. Hot damn.

Beautiful Madonna ❤ love her voice here pure she never backs down ..ever! 💖.

Miss that Madonna!!!nowadays I don t recognize her anymore.... 😢

her honesty always amaze me: she's the only one I know who can be badass and cute at the same time.

Great example of her talent and gorgeous vocals.

These two are hilarious together...I could watch these two banter for hours...back and forth give and take

Everytime Madonna meets Dave, it'll be a home run..

A totally different Madonna, Magnifique, natural and sweet. Beautiful voice ❤

Beautiful song. Thanks Madonna

No auto tune/pitch correction and I’m fine with that. Great performance!

Lovely version of Don’t tell me.

Love their location interviews cause they are both quick and witty! The queen forever 👑👑👑

I love the dynamic between these two it's just... down to earth.

I Love Modana! It goes back my days when good Songs music was astonishing.

She is so sweet! And she sounds great! Lifelong crush. xoxo

Very inteligent Lady.....❤ thank You Madonna to be with us!

Over 2 decades ago I think i love guitar playing madge alot more than i do the smoothy cream pop goddess. Great ballad,n I miss you too Dave

My God she stook up for herself brilliantly

Absolutely agree, I remember first knowing her in 1984, MTV

Erotica was a beautiful revelation for our ears and eyes. What a great piece of art!!

She’s so cute here and her voice sounds good.

In this interview she seems so humbled. Children will change a person so fast. I totally appreciate how calm, cool, and collective she is here. It makes her that much more sexier and attractive to me. And I was that guy in the 80s that would not listen to any of her music at all.

she's amazing, smart talented, beautiful and a great sense of humor.

She was on the right track to get older in style: Look, outfit, hair and makeup, body and most importantly the music was on point. And then Hard Candy and 5 other albums and surgeries happened!

I love you Madonna!!!

Madonna is an Icon. Love her work. This was married Madonna. You can't hold her spirirt. She is a free spirit. I wish her the best on her Celebration Tour 2023. She will do well.

I love this woman so much

Drink a Guinness, that's my girl. Hello from Ireland 🇮🇪 everyone, imagine if Madonna said hello to me lol. I'd faint.

I’m impressed by her guitar playing it’s really hard to sing and play at the same time

OMG, just listen, thank you

Beautiful lady and artist❤❤

loved the song, oozing raw talent, such an icon ❤

Madonna and David how I love these 2 together!

I will always love Madonna 🎉❤

She’s fed up of being asked questions that people ask her just because she’s a woman. She has a career and that’s why she’s there, so she wants to be asked about that, rather than motherhood and patronising questions that people don’t ask men.

I always regarded Madonna work as silly and frivolous till the day I watched the videoclip of 'Frozen' on MTV Brasil. I also noticed she irradiated a different glow, the kind only real stars are capable of. And all of this is confirmed on this interview.

Definetly talented!! And television does her no justice she is more beautiful in person!!

LOVE LOVE LOVE her!

Madonna is a Queen! I've loved her, music, dance, creativity, and her messages since I was a little girl, the first song I loved of hers was Lucky Star when I was 7 years old in 3rd grade and still love her today at 44 years old. She puts out great music and she is a true entertainer!! And just to think she never thought she was a singer or actress but just a dancer.

18:28 "creamy smooth pop icon goddess" lol This is Monte's first public gig with her ..... he's been with her ever since.

Love Madonna 👏 great job

…wow, what a haunting version of this great dance pop tune

This is Madonna at her best. Holy hell, this woman right here is a Goddess. So smart and her laugh is intoxicating.

Damn her! If THIS Madonna could see what she's become in 2022, she's lose her mind. God, I miss THIS Madonna!!!!

Awesome! Loved the Show 👍

I miss grown up madonna

That Madonna is something I tell ya, and Letterman is funny! Great show!

Love her hair very plain down to earth

She looks great. She's one smart cookie.

Motherhood, cleaned her up quite well ! 🙏😎🙏

i like the song and her outfit

She's amazing!❤