Confessions Lightside

I would recommend "Early Years" (with Otto von Wernherr)

just kidding

I wouldn't start with a studio album. I would just recommend the 2 cd version of Celebration or the DVD (or the Confessions tour DVD) and then let that person decide which tracks/eras to start discovering.
The easy answer would be telling Confessions, Ray Of Light, True Blue or Music but all her albums are so different from each other that starting from a compilation would give that person a bigger perspective to choose where to start from (that's why I also mentioned the music DVD and the Confessions Tour, Madonna's visuals are increible).

I would recommend "Early Years" (with Otto von Wernherr)

just kidding

My friend is a swiftie and I suggested her Ray of light and Confessions. She loved both albums. She also liked Rebel Heart. It totally depends on their music interest and age etc. 

If it's someone i hate i would recommend "Madame X"

It completely depends on what kind of music they are into.
Pop fans? Confessions or Rebel heart
Classic rock fans? Like a prayer
Electronica and ambient fans? Ray of light
Jazz and spoken word fans? Erotica or I'm Breathless
90's ballad fans? Bedtime stories
Broadway fans? Evita
R'N'B fans? Madonna
Hip hop fans? Hard Candy... I guess?
Taylor Swift fans? True blue or Music (The Immaculate Collection would be better)
Disney fans? I'm Breathless

Ray of Light or Confessions

If you had someone (who was very interested in Madonna, but, hadn't listened to any of her studio albums in full yet) ask you which "studio" album of Madonna's would you recommend for them to listen to first, which album would you choose? I'd choose "Confessions On A Dancefloor". I love how it's structured like a "DJ set". You can dance to it and it's still relevant to this day. I think they'd only want MORE after listening to it.

Oh this is like choosing a favorite child:
BAT the first I saw live so that’ll never get it out of the first place. 
CT
RHT the best feeling of joy and happiness in a concert ever 
Celebration
MDNAT
TGS this place is because I always have trouble remembering how good it was 
S&ST
RIT/MX can’t place one over the other 
VT I worshiped this one when I was 14 but didn’t see it live
DWT didn’t see it live
WTGT didn’t see it live 
 

1. Confessions Tour
2. Re-Invention Tour
3. Virgin Tour
4. Drowned World Tour
5. Celebration Tour
6. Blond Ambition Tour
7.  Who's That Girl? Tour
8. Rebel Heart Tour
9. MDNA Tour
10. Sticky & Sweet Tour
11. Girlie Show
12. Madame X Tour
 

The Confessions Tour Drowned World Tour 2001 Sticky & Sweet Tour Re-Invention World Tour The Girlie Show MDNA World Tour Rebel Heart Tour The Celebration Tour Blond Ambition Tour Who's That Girl World Tour The Virgin Tour Madame X Tour The Confessions Tour will always be number one to me. ^^
 

The Confessions Tour Drowned World Tour 2001 Sticky & Sweet Tour Re-Invention World Tour The Girlie Show MDNA World Tour Rebel Heart Tour The Celebration Tour Blond Ambition Tour Who's That Girl World Tour The Virgin Tour Madame X Tour The Confessions Tour will always be number one to me. ^^
 

Yeah I think so too - regardless on whether MDNA was a good album the interest was there for it when it was launched and think people were hoping for something better than Hard Candy after a 4 year wait between albums but I think the single choices were so poor the interest quickly dropped upon release though. Had Warners been involved I think we would have got a different version of the album with some of the tracks worked on a bit more and better single choices and promotion and most likely a set list on the tour that had more hits like she did for Re-Invention after American Life perform as well as Music and Ray of Light commercially.
When she attended the premieres around the world for W/E around the same time the public went crazy to see her on the red carpet and not so much the actors in the film - was so obvious everyone was far more interested in Madonna being there - so think there was still so much interest around the time of MDNA anticipating it's release.
I do think the move from Warners and not having their expertise and clout with promotion and when Liz Rosenberg retired too that didn't help and was around the time she seemed to do alot of celebrity endorsements that I don't think helped her brand and how interested people were in her as an artist compared to period before 

As many have said, Madonna was relevant to the general public until 2012 with her participation in the Super Bow, after the launch of MDNA the decline began for that public.

I agree Superbowl was the last huge moment. Of course she still attracts attention, but after 2012 we got a lot less press coverage, not to mention radios. The ridiculous internet crap doesn't count imo.
Let me give you an example. For every new record or every tour Italian newspapers used to dedicate a full page to Madonna, sometimes even two. I used to buy at least the main 4 Italian newspapers to read reviews etc. This hasn't happened with Rebel Heart and even less with Madame X. As I said already, almost nobody noticed MX was released in Italy. And Italy is the nation where even Gambler, Oh father, Love profusion and Girl gone wild charted!

I'd say Eurovision...

"Confessions" was a huge GP era. It was cool to love Madonna again.

"4 Minutes" was a monster hit in 2008 and one of the pop songs of that year, it was everywhere. A proper international hit and her last one so far.
The "Sticky & Sweet Tour" was a huge success too.
And then the Super Bowl in 2012.
I know some fans don't like the "Hard Candy" era that much and have "Confessions" as her last peak, but let's not rewrite history...

I personally find all Deadpool movies awesome, so I'm actually really happy about that, can't wait to see the movie & hope that LAP is feature in some scene  

I love that she performed "Bad Girl" and "Bedtime Story" <3

I love that she performed "Bad Girl" and "Bedtime Story" <3

I love that she performed "Bad Girl" and "Bedtime Story" <3

I love that she performed "Bad Girl" and "Bedtime Story" <3

I love that she performed "Bad Girl" and "Bedtime Story" <3

I love that she opened her show  with NRM. cz nothing can go wrong when you open a show with a ROL song