Ray of Light
American Life
Confessions on a Dancefloor
Bedtime Stories
Erotica
Music
Rebel Heart
Like a Prayer
Hard Candy
Madonna
Like a Virgin
MDNA
True Blue
The only good thing about her first three albums are the singles, basically.
All of them are soo different so it depends on the mood and what genre of music you most enjoy. There is always songs on her so called "bad" albums that are amazing.
Best IMO are:
Ray of light, Erotica, American Life And Rebel Heart.
There's at least two gems in each one of her albums. My top 5 albums as a whole are as follows (in no particular order):
Confessions on a Dancefloor
Bedtime Stories
Ray of Light
Rebel Heart
Erotica
1. American Life
2. Ray of Light
3. Confessions on a Dance Floor
4. Erotica
5. Bedtime Stories
6. Like A Prayer
7. Hard Candy
8. MDNA / Like A Virgin
9. Rebel Heart
10. True Blue
11. Music / Madonna
Listen to Ray of Light, if you like it a lot, listen to American Life & Confessions next, if not, listen to Erotica and Bedtime Stories next, at any point you can listen to Immaculate Collection for a taste of her 80s music to figure out if you'll like it (some of it sounds date, some of it sounds amazing). Music is a stepping stone between ROL and AL but it's not too important outside of it's lead single, Hard Candy and MDNA are the desserts to her main course of a discog. Rebel Heart is cute but look at it as a collection of songs instead of looking for cohesion, but you'll probably still end up finding more gems in it than MDNA/Hard Candy, my above list is just personal preference. 80s can be listened to in any order but it's best to probably go Madonna then True Blue then LAV then LAP for a more even and upward sloping experience quality wise.